Vacation Home Rentals By Owner In Chatham, MA

$1113.91

Blue water views and coral sunsets from every room in this beautifully appointed home.

Chatham, Massachusetts, United States

Experience the charm of Chatham in this beautifully appointed rental, perfectly situated with stunning views of Oyster Pond and just a short stroll to downtown.brRelax on the decks as you soak in the breathtaking sunsets and enjoy the refreshing breezes. This home comfortably sleeps 7 guests across 3 bedrooms. The first-floor suite features a queen bed and an en-suite bathroom with a shower. Upstairs, you'll find a queen bedroom with an en-suite bath, and another en-suite bedroom furnished with 3 twin beds and a twin trundle. A beautiful wet bar and sitting area provides seamless access to the upper deck, offering captivating views of the water, where coral sunsets meet shimmering blue waters. The first floor boasts an open and airy living area with a large kitchen island, flowing out to a private brick patio in the backyard. Imagine grilling dinner under the stars before heading into town for a movie or ice cream. An enclosed outdoor shower is perfect for rinsing off after a day of swimming in the surf. For additional space and comfort, there's a large family room in the finished basement, along with central A/C and Wi-Fi throughout the home. This rental also provides a complimentary Welcome Bag, a reusable tote filled with essential paper and cleaning products for your stay, courtesy of the owner. Contact us at Chatham Rentals, and let us help you plan your memorable stay!

Bed

Bath

Sleeps

$810.17

/ Nightly

Private Vacation Home

Charming house located in the heart of downtown Chatham!

Chatham, Massachusetts, United States

This charming house, with a shared driveway, is located in the heart of downtown Chatham. Leave your cars parked and a short walk brings you to The Chatham Library, The Candy Manor or Oyster Pond Beach. Stroll downtown to get your morning coffee and paper, or for dinner and a movie in the evening. This 3 bedroom, 2 bath main house offers 3 twins, 1 king, 1 queen and a double bed. Slimline a/c units are in the bedrooms and a window unit cools you down in the downstairs living area. A private back deck to relax and rejuvenate on, or to grill up some dinner while the stars begin to peak out. Spacious updated kitchen, laundry, dining area and family room are on the 1st floor. Take a walk up the original Captain's Stairs to the 2nd floor and you'll find a private bedroom, an Apple TV lounging room and 2 more bedrooms that are adjoining. Please note if you are not familiar Apple TV, speak with an agent prior to booking. Great location and home for a great Cape Cod getaway. Call us at Chatham Rentals and let us help you plan your stay. This rental includes a reusable tote starter pack of cleaning and paper products, compliments of the owner.br** Please note: Captain's Stairs are narrow and steep, the 3rd bedroom is a walk through, and there are 2 other rental properties adjacent on lot**

Bed

Bath

Sleeps

$823.62

/ Nightly

Private Vacation Home

The Cape Escape: Walk to Harding's Beach

Chatham, Massachusetts, United States

4 Bedroom- 2 Bathroom- Sleeps 8brA 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of our homes offer flexible stays with a 3 night minimum in the off season - ask our Reservation Specialists for more details.brWe offer a 4pm Check-In and 10am Check-Out brbrOwners Share Why I Love My Home:brThe beach is so close we don't worry when the kids want to take off and head down for a few hours! There is plenty of room to spread out and relaxing on the back deck is also a favorite pastime. We hope you make great memories while in our home!brbrLet Us Tell You About This Home:brNew for 2022 - slimline air conditioning units to keep you cool. Enjoy the convenience of central air conditioning with the ability to set personal temps in each bedroom!brbrCalling all beach goers!! You are a 5 minute walk to the sandy shores of Harding's Beach and the beautiful dune walk to the Stage Harbor Lighthouse! Great location - with a sidewalk down Hardings Beach Road for safe walking with the family! You can even bring Fido on the Dune walk all year round!brbrOnce you are here - set your bags down and enter into an open living and dining area with a large flat screen TV and working fireplace - as well as lots of comfy seating. Off the dining room is an open galley kitchen that is fully equipped and offers easy access to outside deck for your outdoor dining pleasure. There is a gas grill as well as a charcoal grill for your use. Off the kitchen is Bedroom #1 with 2 Twin beds. There is also a bathroom with shower on this main floor. The washer/dryer is located off the kitchen for your convenience.brbrHead upstairs to 3 more bedrooms and a full bath with tub/shower combo. Bedroom #2 has a King Bed and a Flat Screen TV, Bedroom #3 has a Queen Bed and Bedroom #4 has a Queen size futon (great kids room).brbrOutside is the large back deck to enjoy perfect Cape Cod evenings. There is an enclosed outdoor shower with hot and cold water for you to enjoy and wash those sandy toes off when you return from the beach. There is also a partially fenced in yard offering nice privacy. brbrAccess to association dock and picnic area in Harding's Hills Association as well!brbrCome enjoy this Cape Escape - put your toes in the sand and a drink in your hand and make memories with us in Chatham! brbrFree Tickets and Complimentary Activities! Create unforgettable memories and experience Cape Cod like a local! Enjoy $750 worth of daily exclusive free tickets to exciting local attractions through our partnership with Xplorie. Your amenities include activities such as Island Cruises, Whale Watch, Bike Rentals and admission to Whydah Pirate Museum. When you're not soaking up the sun on the beach, enjoy daily rounds of golf at Cranberry Valley or Chequessett Golf Courses and mini-golf for family fun.brbrThis home offers Keyless Entry for your convenience. brNO SMOKING of anything containing tobacco, any other substance, and e-cigarettes, inside or outside of the home.brPET FRIENDLY HOMES are for a DOG only. This home allows 1 dog for $25 per night. With owner approval, a second dog may be considered for an additional $25 nightly fee. A Pet Registration form must be completed upon reservation confirmation. brMax parking of cars at property: 3 No parking on lawn anytime. brFireplaces are only available for use in the winter months with advance approval from owner. brTown of Chatham Rental Certificate: STR-389brbrAdditional Information to Assist You:brOur calendars are updated in real-time and are accurate.brDeparture cleaning is included with your reservation at no additional charge. Simply follow our basic check-out instructions at your departure. brState and local taxes are charged if applicable. brFor Reservations made over 60 days away, you will make two payments - 50% initial payment with reservation and the final balance will be auto billed to your credit card 60 days prior to arrival. We accept Mastercard and Visa for payments.brA confirmed reservation is non refundable--please consider purchasing trip cancellation insurance. Ask our guest specialist for more details regarding cancel options and trip insurance. br***Linens - bed sheets, bath/dish/beach towels and bath mats are not included with this home but can be rented at time of booking or at a later date through our linen rental partner. Please ask our guest specialist for details. Our NEVR Homes come with mattress covers, pillows and a bed cover such as blanket, quilt, bedspread etc.brYou must be 25+ years old unless accompanied by a parent or guardian to book one of our Vacation Rental Homes. An ID must be furnished upon request. brArea Informationbr0.3 mile to Harding's Beachbr0.6 mile to Chinese take out & Shop Ahoy! Liquor Storebr0.6 mile to Larry's PX - eat breakfast with the locals! br0.7 mile to Mom & Pops Burgers - next door is D'Angelos where you can get your subs for the day at the beachbr1 .0 mile for ice cream and the best fried clams on Cape Cod at Kream N Konebr1.4 mile to the Bike Path on George Ryder Road br1.4 mile to New England Pizza Housebr1.8 miles to Del Mar Bar & Bistro - Excellent dining and cocktails!brbrA short drive (2.3 Miles) into downtown Chatham where you will find :brThe Orpheum movie theaterbrSeal toursbrShoppingbrRestaurantsbrFriday night Band stand concertsbrThe Monomoy TheaterbrPlaygroundbrPublic TennisbrChatham A's Baseballbrbr*Mileage is approximate

3

Bed

2

Bath

8

Sleeps

$1959.95

/ Nightly

Private Vacation Home

Luxury Home with Pool, Hot Tub & Water View

Chatham, Massachusetts, United States

Summary:brbr16696 - Kingdom on the Cove: Luxury Home with Pool, Hot Tub & Water ViewsbrbrbrbrThe Space:brbrDiscover a serene and luxurious escape at this luxury Chatham home—a five-bedroom, five-and-a-half-bath haven that promises both comfort and convenience. Perfect for families and groups, this spacious home accommodates up to 12 guests, offering a seamless blend of elegance and relaxation. Inside, you'll find five well-appointed bedrooms and five and a half bathrooms spread across two floors, each exuding warmth and coastal sophistication. brbrEnjoy the central gas fireplace, a cozy spot for storytelling and laughter. The chef's kitchen, equipped with modern appliances and a coffee maker, invites culinary adventures inspired by the ocean's bounty. Step outside to the expansive and well manicured grounds. Equipped with a luxurious heated pool and hot tub, fire pit, and stunning views of the cove, you'll never have to leave the backyard to take in the beauty of Cape Cod's pristine waters. In the evening, head on over to the stone patio, where a gas fire pit beckons for marshmallow roasting under the stars. brbrA 10 minute drive will take you to downtown Chatham, with cullinary delights, local boutiques, and the Chatham Orpheum Theater, entertainment abounds. To connect with nature, explore the pristine beaches of Jacknife or Lighthouse Beach; dive into thrilling water sports on Oyster Pond or Pleasant Bay. Kingdom on the Cove is the perfect spot for relaxation and exploration - and where unforgettable memories begin. Reserve your stay at this enchanting coastal home today and experience the magic of Chatham firsthand. Your seaside sanctuary awaits.brbrHome Details:br-No Pets(Fines Remitted)br-Sleeps 12brBedroomsbr-Total 5br-1st Floor Bedroom: 1 King br-2nd Floor Bedroom: 2 bunks w/ 4 Twinsbr-2nd Floor Bedroom: 1 Kingbr-2nd Floor Bedroom: 2 Twinsbr-2nd Floor Bedroom: 1 Kingbr-Bathroomsbr-Total 5.5br-1st Floor: ½ bathbr-1st Floor: Showerbr-2nd Floor: Showerbr-2nd Floor: Showerbr-2nd Floor: Showerbr-2nd Floor: ShowerbrOther Amenities br-Heated Pool available May 15-September 15 annuallybr-Central A/C br-WiFibr-Smart TVbr-Streaming Servicebr-Washer/Dryerbr-Propane Grillbr-Gas Fire pitbr-Outdoor Showerbr-Please note outdoor amenities are available seasonallybr-Please note the garage is not for guest usebr-Please note there is an exterior camera facing the drivewaybr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-Parking for 4 cars maximumbr-C0557840550brbrbrbrOther Things to Note:brbrPlease note there is a camera facing the driveway and the garage is not for guest use

5

Bed

5

Bath

12

Sleeps

$2169.5

/ Nightly

Private Vacation Home

Pool, Hot Tub, Water Views and more!

Chatham, Massachusetts, United States

Summary:brbr16697 - Ultimate Escape: Pool, Hot Tub, Water Views and more!brbrbrbrThe Space:brbrWelcome to the Ultimate Escape, two expansive homes providing luxury and comfort for up to 18 guests, making it the perfect retreat for your whole family or group of friends. Lounge by the pool, soak in the hot tub, work on your free throws, and watch a movie on the big screen without having to leave the comfort of this sprawling two-home estate. Should the sea call to you, you can walk a convenient one tenth of a mile to a private neighborhood beach where you can work on your tan or cool off in the water. brbrbrbrWith eight generous bedrooms and seven bathrooms (6 full, 2 half) spread across two buildings, every guest enjoys space and privacy. Unwind in the chef-caliber kitchen or sumptuous living areas, then gather for evening fun in the game room upstairs—complete with a pool table and bar—or relax in the soothing embrace of the hot tub. Upstairs, the master suite offers direct deck access and sweeping pool views, while outside, a sprawling stone patio begs for lingering conversations over dinner or drinks.brbrbrbrBeyond the sparkling pool, you’ll find a half basketball court for friendly competition and a spacious yard perfect for lawn games. Rinse away the beach day under the stars in your own outdoor shower, then gather around the fire pit for storytelling and stargazing.brbrbrbrA two-minute stroll brings you to tranquil waterfront sands, or venture a bit farther to explore Chatham’s famed Ridgevale and Hardings beaches. Treat yourself to local flavors at The Impudent Oyster or Del Mar Bar & Bistro, both just a few miles away.brbrbrbrWhether sunbathing by the pool, exploring Cape Cod’s beaches, or reconnecting with loved ones in stunning surroundings, the Ultimate Escape promises memories you’ll cherish forever. Secure your unforgettable Cape getaway—book Ultimate Escape today before someone else claims your dates!brbrbrbrHome Details:brbr-Dogs Welcomed (w/fee of $45/night per dog)brbr-Sleeps 18brbrBedroomsbrbr-Total 8brbrFirst House (5):brbr-1st Floor: 1 Queenbrbr-2nd Floor: 1 King | Master | Ensuitebrbr-2nd Floor: 1 Kingbrbr-2nd Floor: 2 Twinsbrbr-2nd Floor: 1 Queen + 1 TwinbrbrSecond House (3):brbr-1st Floor: 1 Queenbrbr-2nd Floor: 1 Kingbrbr-2nd Floor: 2 Twin+1 Trundle TwinbrbrBathroomsbrbr-Total 7 (6 full, 2 half)brbrFirst House (3 full, 2 half)brbr-1st Floor: Full, Tub + Shower (ensuite)brbr-1st Floor: 1/2brbr-2nd Floor: Full, Tub + Showerbrbr-2nd Floor: Full, Shower (ensuite)brbr- 2nd Floor: 1/2 (ensuite)brbrSecond House (3 full)brbr-1st Floor: Full, Showerbrbr-1st Floor: Full, Showerbrbr-2nd Floor: Full, Tub/Shower CombobrbrOther Amenities brbr-Central AC and Mini Split ACbrbr-WiFibrbr-Smart TVbrbr-Streaming Servicebrbr-Washer/Dryerbrbr-Propane Grillbrbr-Firepitbrbr-Outdoor Showerbrbr-Heated Pool (available Memorial Day - Labor Day)brbr-Hot Tub (available Memorial Day - Labor Day)brbr-Gas Fireplacebrbr- Pool Tablebrbr-Please note outdoor amenities are available seasonallybrbr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbrbr-Cleaned with Hospital Grade Disinfectantbrbr-Parking for 7 cars maximumbrbr-C0558700550brbrbrbrThe Neighborhood:brbrOceanside

8

Bed

7

Bath

18

Sleeps

$925.59

/ Nightly

Private Vacation Home

Three-bedroom house is nestled in a peaceful neighborhood and features a fully fenced yard.

Chatham, Massachusetts, United States

This delightful three-bedroom house is nestled in a peaceful neighborhood and features a fully fenced yard, perfect for your family and dog. Conveniently located near Jacknife Beach, the home includes 3 bedrooms (2 queen beds, 1 full), 1.5 bathrooms, and a sunny open living area ideal for relaxing together. Upstairs, you’ll find all the bedrooms, along with a full bathroom. Central AC throughout the upstairs and 2 mini splits downstairs to keep you cool on those warm summer days. Enjoy your morning coffee in the charming sunroom while admiring the blooming backyard gardens and koi pond. After a fun day at nearby Jacknife Beach, rinse off in the private outdoor shower before playing with the dog or family in the spacious fenced yard. You’re just a short drive from town for shopping, movies, ice cream, or a baseball game. Upon check-in, the owners provide a Welcome Bag: a reusable tote with starter paper and cleaning supplies for your stay. This inviting home is ready to help you make lasting vacation memories, year after year. Dog friendly (one dog up to 30 lbs; $150 fee applies). Call Chatham Rentals to plan your visit!

Bed

Bath

Sleeps

$342.21

/ Nightly

Private Vacation Home

Renovated cottage 1 mile to beach in Chatham!

Chatham, Massachusetts, United States

Totally renovated bungalow style cottage with a sunny open floor plan, brand new appliances and furnishings on quiet street convenient to everything Chatham!! After the beach, rinse off in the private outdoor shower before relaxing on the sunny patio. brTwo bedrooms, one king and two twin beds , 1 full bath . Dining area with room for 6 people. Fenced in backyard area with patio. This house is convenient to shops, restaurants, beaches, public bike paths. Golf courses and tennis courts are all easily accessible. Central heating and air conditioning keeps the cottage comfortable regardless of the weather.brbrThe center of Chatham is a quaint village is less than 2 miles east on Rte 28. It’s streets are lined with many shops, eateries & a Movie Theater. Every Friday evening, in town, there is a band concert you do not want to miss.brbrThere are so many activities to do and see in Chatham. Boating, Fishing, Biking on a dedicated bike trail, Seal Cruises visiting the Commercial Fish Pier, the Coast Guard Station to name a few. There are several beaches near by. The closest are Ridgevale & Hardings Beaches a little over a mile. Daily or Weekly beach stickers for Ridgevale, Hardings, Cockle Cove and/or parking along Bridge St for Lighthouse Beach are available at the kiosk in the beach parking lots. Harwichport is a few miles west. Both favorite spots for a day of shopping or a night outbrbrFor bikers it is easy to pick up the Old Colony Rail trail to Harwich where it connects to the Cape Cod rail trail that runs 22 miles from Dennis to Wellfleet.brbr*Amenities include central air, microwave, Keurig coffee maker, toaster, dishes and utensils, pots & pans, grill & high end appliances. Linen and towel rental service available by request. Paper towels, toilet paper, cleaning spray, broom, vacuum, dish soap, dish washing pods are provided. Please note there is no washer & dryer, no hairdryer, no beach chairs & no dishtowels for kitchen. brbr*2 Car Maximum

Bed

Bath

Sleeps

$668.72

/ Nightly

Private Vacation Home

Star of the Sea - Newly Renovated Cape House .9Miles from the Beach

Chatham, Massachusetts, United States

Escape to Star of the Sea a charming 2 story Cape house in South Chatham, MA. This delightful newly renovated rental features 2 bedrooms, 1 bathroom, and sleeps up to 7 guests. brbrSituated on Main St (Route 28), it offers central convenience. Close to beach and on the bike trail! Cockle Cove Beach just 0.9 miles away. Step into the backyard and access the Cape Cod bike trail. Unwind with an outdoor shower, fire up the grill, and take advantage of ample parking. Your perfect vacation retreat awaits!--brbrThe space:brStep into the living room featuring a sectional couch and two pull-out loveseats along with a large sectional couch. Continue to the open-concept dining room and renovated kitchen, then explore the large backyard with its grill, fire pit, and beach gear. Plus, full access to the Cape Cod bike path from the rear stairs.brUpstairs, discover the bathroom and bedrooms, including a queen bed and loveseat pull-out in the master and twin beds in the second.brOff the house, enjoy exclusive access to a brand new entertaining deck, with built in bench, string lights, and outdoor shower. brbrAir-conditioned, clean, new bathroom, basement W&D. brGuest accessbrYou have exclusive access to the outdoor shower connected to 2212. You have exclusive access to your half of the backyard. Picture from the corner of the property (starting in the middle) to the edge of the property line. Access to the rear stairs leading to the bike path is shared by both properties.brbrOther things to notebrCockle Cove beach is .9miles away. If you follow main street you will be in downtown Chatham within 5 minutes. In downtown you can access places like The Squire, Chatham Bars Inn, and various other retail stores and restaurants. You can book both properties on the lot if you notify us.

Bed

Bath

Sleeps

$580.8

/ Nightly

Private Vacation Home

NEW LISTING Peace and Quiet Pond Front

Chatham, Massachusetts, United States

Watch the sunset Mill Pond.brSurrounded by nature the tranquility is perfection.brJust minutes to Chatham Light, Cockle Cove and Hardings Beach. Convenient to many excellent golf courses including Chatham Links, Cranberry Valley, Captains, Dennis Highlands and Dennis Pines to name a few. Shopping and great restaurants are all within a short drive or walk to the best Tacos on the Cape at The Corner Store.brFirst floor master. Basement laundry.brGas Fireplaced Family Room with a full wall of sliders to the oversized deck with privacy and pond views.

Bed

Bath

Sleeps

$1473.8

/ Nightly

Private Vacation Home

Spacious Lakefront Escape - Perfect for Families

Chatham, Massachusetts, United States

Welcome to our spacious lakefront home, perfect for families and large groups! With two master suites, four additional bedrooms, and 11 beds, the house offers flexible sleeping arrangements to fit your needs. Ideal for remote work, the home features fast WiFi, air conditioning, and dedicated office setups in three bedrooms. You’ll find 3.5 bathrooms plus a refreshing outdoor shower.brEnjoy stunning lake views, swimming, fishing, and cooking in the fully equipped gourmet kitchen. The lower level is made for fun, offering ping pong, foosball, board games, and yoga mats.brLocated close to scenic bike trails, beautiful beaches, and the charming shops and restaurants of Chatham Main Street — the best of the Cape is at your doorstep! Note- This rental does not include linens and towels. Our guests bring their own or use capelinenrentals.com for service.

Bed

Bath

Sleeps

$819.51

/ Nightly

Private Vacation Home

Azure Cottage: Central A/C & Hot Tub

Chatham, Massachusetts, United States

3 Bedrooms- 3 Bathrooms- Sleeps 8brA 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of our homes offer flexible stays with a 3 night minimum in the off season - ask our Reservation Specialists for more details.brGuests can bring their own linens or rent from our Linen Service for an extra fee (Bed Sheets, Bath, Beach and Kitchen Towels)brWe offer a 4 pm Check-In and 10 am Check-OutbrbrUpdated Cape Cod home is Dog friendly with central A/C, WIFI, and a Hot Tub. Welcome to Azure Cottage located on a 3/4 acre serene setting in the Oyster Pond area of Chatham. It is ON THE LITTLE LOOP right off Cedar Street, is less than a mile to down town Chatham and is close to town landing. Private setting yet close to all the Chatham has to offer! brbrThis home is in such a great location being close to Chatham and Oyster Pond. We love that it is set back and very private. We always feel like we are away from it all when we are there and can just kick back and relax. Just as the sun is setting you'll find us in the hot tub going through the day's memories and planning tomorrow's adventure.brbrLet Us Tell You About This Home:brEnter through the side door and you will notice the beautiful wide pine floors that run throughout this Charmingly Refreshed Coastal home. brOn your right is Bathroom #1 full bath in cool coastal decor. The entry way leads you into the combination dining and living area, with ample room for the whole family to eat a great meal at the dining table or relax on the comfy L shaped couch and watch a favorite movie on the flat screen TV.brbrThe slider leads you to the outside deck with ample seating and grill for your nightly BBQ. Bedroom #1 is off the living room with a Queen sized bed , dresser and closet. The Kitchen is right across from the dining area which also leads you to the rest of the home.brbrThe open kitchen is contemporary with stainless steel appliances including dishwasher, sky blue cabinetry and sunken sink. The laundry is located in the double closet off the kitchen for convenience. Down the hall off the kitchen are Bedroom #2 on the right with a King Bed, dresser and closet. Bedroom # 3 also on the right offers a King bed, with dresser and double closet. Bathroom # 2 is at the end of the hall with a full bath with tub shower combo (perfect for kiddos after the beach).brbrHead back towards the kitchen and the entrance to the finished basement and hot tub is on the left. Imagine watching the sun set and the stars start to appear all from the vantage point of the bubbly hot tub!brbrHead downstairs to a tastefully decorated finished sitting area with couch, flat screen TV and day bed with trundle for extra sleeping. Great area to let everyone hang out and watch movies while the adults are upstairs planning dinner. You will also find bathroom number #3 with tub and shower combination. brbrThe slider leads you to a patio with Adirondack chairs for relaxing. Enjoy an outdoor shower before you relax in the hot tub in the private back yard. brbrBring your kayaks and paddle boards - there's easy access to the Town Landing off of Battlefield Road. brbr**Most NEVR Pools/Hot Tubs are open from Memorial Day Weekend thru Labor Day Weekend. Please feel free to check with NE Vacation Rentals and the home info -- to confirm exact dates when the pool and/or hot tub is opened or closed for the season**brbrIf you're looking for privacy, this home has that and more!!brbrFree Tickets and Complimentary Activities! Create unforgettable memories and experience Cape Cod like a local! Enjoy $750 worth of daily exclusive free tickets to exciting local attractions through our partnership with Xplorie. Your amenities include activities such as Island Cruises, Whale Watch, Bike Rentals and admission to Whydah Pirate Museum. When you're not soaking up the sun on the beach, enjoy daily rounds of golf at Cranberry Valley or Chequessett Golf Courses and mini-golf for family fun.brbrWith all NEVR properties, we think of the little things to make your vacation special. Our Guest Welcome Bag, compliments of the homeowner, contains starter quantities of kitchen and bathroom essentials, with a few locally sourced snacks as well (subject to change based marketplace availability).brbrThis home offers Keyless Entry for your convenience with. brNO SMOKING of anything containing tobacco, any other substance, and e-cigarettes, inside or outside of the home.brDOG FRIENDLY HOMES are for a DOG only. This home allows 1 dog for $25 per night. With owner approval, a second dog may be considered for an additional $25 nightly fee. A Pet Registration form must be completed upon reservation confirmation. brMax parking of cars at property: 3. No parking on lawn anytime. brTown of Chatham Rental Certificate: STR-421brbrAdditional Information to Assist You:brOur calendars are updated in real-time and are accurate.brDeparture cleaning is included with your reservation at no additional charge. Simply follow our basic check-out instructions at your departure. brState and local taxes are charged if applicable. brFor Reservations made over 60 days away, you will make two payments - 50% initial payment with reservation and the final balance will be auto billed to your credit card 60 days prior to arrival. We accept Mastercard and Visa for payments.brA confirmed reservation is non refundable--please consider purchasing trip cancellation insurance. Ask our guest specialist for more details regarding cancel options and trip insurance. br***Linens - bed sheets, bath/dish/beach towels and bath mats are not included with this home but can be rented at time of booking or at a later date through our linen rental partner. Please ask our guest specialist for details. Our NEVR Homes come with mattress covers, pillows and a bed cover such as blanket, quilt, bedspread etc.brYou must be 25+ years old unless accompanied by a parent or guardian to book one of our Vacation Rental Homes. An ID must be furnished upon request. brbrArea Information:br1.2 miles to Oyster Pond for swimmingbr1.5 miles to the village of Chatham for shopping, ice cream, band concerts and more!br1.6 miles to the ballfield to watch the Chatham A's or to the Children's Playgroundbr1.8 miles to the bike path at Stepping Stones Road - More info on The Rail Trail can be found here: Info on Cape Cod bike trailsbrUnder 2 miles to all of the local activities and things to do: Lighthouse beach, The Fish Pier for great seafood or a seal cruise - or boat to the outer beach! The beach bar at Chatham Bars Inn (Open to the public) or take in a massage or facial at Le' Petite Day Spa! What ever you do - this house offers the perfect location for you to have fun!br*Mileage is approximate

Bed

Bath

Sleeps

$4415.39

/ Nightly

Private Vacation Home

Sophisticated Chatham Oasis with Pool & Spa RPAM062

Chatham, Massachusetts, United States

Welcome to 84 Doane Road in Chatham, MA, where opulence meets comfort and convenience. Nestled in a prime location just .3 miles from Main Street, this 5+ bedroom / 7 full 2 half bathroom luxury property offers everything you need for an unforgettable getaway and can accommodate up to 12 guests in 7,000+ sq ft (all 3 levels). As you step inside, you'll immediately be greeted by a sense of elegance and sophistication. The spacious living areas are adorned with tasteful furnishings and stylish decor, creating an ambiance of refined luxury. Relax and unwind in the cozy yet spacious living room, complete with plush seating and a fireplace, perfect for chilly evenings.brbrThe gourmet kitchen is a haven for culinary enthusiasts, equipped with top-of-the-line appliances, sleek countertops, a 12.5 foot island and ample space for preparing delicious meals. Whether you're hosting a dinner party or enjoying a quiet breakfast, the dining area provides an inviting setting with its elegant table and views of the pool and backyard.brbrOne of the highlights of this remarkable vacation rental is the inviting outdoor oasis. Step outside to discover a private, heated pool. Take a refreshing dip in the crystal-clear waters or simply bask in the sun. The attached spa offers the ultimate relaxation experience, allowing you to soak away your cares and unwind in utter bliss.brbrConvenience is key, and this rental truly excels in that regard. With a fantastic location just a short stroll from Main Street, you'll have easy access to an array of charming shops, delightful restaurants, and captivating local attractions. Immerse yourself in the vibrant culture of Chatham and indulge in the area's renowned coastal cuisine.brbrAfter a day of exploration, retreat to the bedrooms for a serene sanctuary. Each bedroom has a private en-suite bathroom and is thoughtfully designed to offer the utmost comfort. Wake up feeling refreshed and rejuvenated, ready to embark on another day of adventures. The finished, walk-out lower level features an additional TV area with an oversized sectional, a full bathroom, a ping-pong table, billiards table, card table and a shuffleboard table. Escape to this exquisite luxury vacation rental in Chatham, MA, and immerse yourself in a world of sophistication and relaxation. Book your stay today and make memories that will last a lifetime.brbrPool and spa are open and heated until 10/4/25 and 5/16/26 to 10/3/26. All linens and towels are provided. Subject to applicable taxes and fees. Please call for additional details. Parking for 6 cars max. No pets or smoking allowed. 7 night minimum rentals during the peak season, Sat. to Sat only. Shorter stays at a reduced rate are available in the shoulder seasons. All Robert Paul Vacation Rental bookings include a non-refundable $250 fee that includes administrative fee and damage waiver insurance for self-reported incidental damage up to $1,000.00. Upon receipt of a booking request, an agent will reach out to discuss additional security protection which may be required at this property.brbrThe home is available for year round bookings. Please see below for minimum stay requirements based on the time of year. Please note, off season bookings do not include the pool or spa. The cleaning fee is reduced as well during these stays.brbrSTAY REQUIREMENTS: brbr8/30/25- 10/3/25- 4 night minimum stays (Pool and Spa are Open)br10/4/25 - 5/15/26 - 3 night minimum stays (Pool and Spa are Closed)br5/16/26 - 6/26/26 - 4 night minimum stays (Pool and Spa are Open) br6/27/26 - 9/4/26 - 7 night minimum stays, Sat. to Sat. only (Pool and Spa are Open) br9/5/26 - 10/2/26- 4 night minimum stays (Pool and Spa are Open) br10/3/26 - 12/31/26 - 3 night minimum stays (Pool and Spa are Closed)brbrBEDROOM CONFIGURATION:brBEDROOM 1- 1 KING (MAIN FLOOR) brBEDROOM 2- 1 KING (SECOND FLOOR) brBEDROOM 3- 1 KING (SECOND FLOOR) brBEDROOM 4- 1 QUEEN / 1 SINGLE (SECOND FLOOR) brBEDROOM 5- 1 FULL / 1 SINGLE (SECOND FLOOR)brBONUS SPACE- 1 KING (SECOND FLOOR / BONUS SLEEP SPACE / ABOVE GARAGE w/ OPEN STAIRCASE WITH NO DOOR)

Bed

Bath

Sleeps

$1609.73

/ Nightly

Private Vacation Home

Steps to Oyster Pond Private Dock!

Chatham, Massachusetts, United States

Summary:brbr16656 - Decked Out Oyster: Steps to Oyster Pond Private Dock!brbrbrbrThe Space:brbrCalling all water enthusiasts! This stunning home has water views and a floating dock just down the street! Enjoy a swim off of your own personal dock or take one of the home’s paddle boards or inflatable boats for a spin! The perfect place to entertain, this home comes fully equipped for eight people, boasting two balconies, a spacious backyard deck, outdoor grill, fire pit and a large well-manicured lawn. But, the fun does not stop there! The home also has croquet and bocce ball sets, an outdoor ping pong table, and foosball table in the basement.brbrThe home's coastal-inspired interior features sun-drenched living areas and plenty of space. On the first floor there is a formal living room with large sofas and a fireplace; a contemporary kitchen with countertop seating as well as a formal dining area; a master bedroom with a king bed and a full, en suite bath; a second bedroom with a queen bed; plus, a third bedroom with a queen bed and office space perfect for working remotely.brbrOn the second floor, there is a family room with a smart TV, board games and a deck for sunset and water viewing; a bedroom with a twin bunk bed; and another bedroom with two double beds and a private deck, as well as a Jack-and-Jill bathroom with jacuzzi tub (and upstairs washer/dryer) shared between both the upstairs bedrooms.brbrChatham Main Street is only a 20-minute walk or a 3-minute drive away from the home; here, you’ll find a fabulous selection of local restaurants and one-of-a-kind stores. Some popular places to dine are The Impudent Oyster, Bluefins Saki and Sushi Bar and The Wild Goose Tavern. Nearby attractions also include movies at the historic Chatham Orpheum; guided tours of Chatham Lighthouse and learning about the Atlantic White Sharks at the Chatham Shark Center. brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 8 br-2 Livable Floors br-1st Floor Master Bedroom: 1 King Bed w/ en suite Full Bathroom (walk-in shower)br-1st Floor Bedroom #2: 1 Queen Bedbr-1st Floor Bedroom #3: 1 Queen Bedbr-2nd Floor Bedroom #4: 2 Full Bedsbr-2nd Floor Bedroom #5: 2 Twin Beds (bunk beds)br-Central Heat & A/C br-Smart TV w/ Cablebr-DVD Playerbr-WiFibr-Washer/Dryer (Basement)br-Foosball Table (Basement)br-Outdoor Ping Pong Tablebr-Spa Tub in 2nd Floor Bathroom br-1st Floor Gas Fireplace (Living Room) for guest usebr-2nd Floor Gas Fireplace (Not for Guest Use)br-Fire Pit br-Private Yardbr-Lawn Gamesbr-Propane Grill br-Paddle Boards & Inflatable Raftsbr-Steps to Oyster Pond with a Private Floating Dockbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrbrbrbrThe Neighborhood:brbrOceanside

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$345.45

/ Nightly

Private Vacation Home

Walk to Water, near Downtown Chatham!

Chatham, Massachusetts, United States

Summary:brbr16692 - Coastal Escape: Walk to Water, Near Downtown Chatham!brbrbrbrThe Space:brbrWelcome to Coastal Escape, a charming Cape Cod vacation home perched atop a serene hill on a private road in Chatham. This inviting getaway offers a spacious layout, perfect for gathering with family and friends.brbrA short, scenic stroll takes you to the private association beach at Ryder’s Cove, where you can enjoy the sand, surf, and breathtaking coastal views. (There is no parking at the beach, but there is a drop-off area). brbrBegin your mornings with a steaming cup of coffee on the back deck, surrounded by the peaceful ambiance of Cape Cod. For a local pick-me-up, visit Chatham Perk, just under a mile away. Afterward, explore the vibrant charm of Main Street Chatham, located a little over two miles down the road, where you’ll find an array of delightful restaurants, boutiques, and the beloved Chatham Candy Manor for a sweet indulgence.brbrFor a dose of history and stunning scenery, venture 2.5 miles to the iconic Chatham Lighthouse, where you can enjoy sweeping views of Aunt Lydia’s Cove and unforgettable sunsets.brbrWhether you’re savoring quiet moments on the deck, exploring the local gems, or relaxing by the beach, Coastal Escape is the perfect backdrop for creating lasting Cape Cod memories.brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 8brBedroomsbrTotal 4br-1st Floor Bedroom: 1 Full Bedbr-1st Floor Bedroom: 1 Twin Daybed w/ Trundle (2 Twins)br-2nd Floor Bedroom: 1 King Bedbr-2nd Floor Bedroom: 1 Queen BedbrBathroomsbr-Total 2br-1st Floor: Full Bathroom w/ Tub/Shower Combobr-2nd Floor: Full Bathroom w/ Tub/Shower CombobrOther Amenitiesbr-Window A/C in bedroomsbr-WiFibr-Smart TVbr-Washer/Dryer br-Propane Grillbr-Indoor Fireplaces are not for guest use (fines remitted)br-Please note outdoor amenities are available seasonallybr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-Parking for 3 cars maximumbrC0522480550

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$472.11

/ Nightly

Private Vacation Home

Idyllic Cape House Close to Beaches

Chatham, Massachusetts, United States

Idyllic cape house close to beaches and ponds, as well as walking distance to restaurants, bars, ice cream, and shops in Chatham! It's a 3 bedroom, 2 bath, with 6 beds, sleeping up to 6 adults and total of 8 people. (NOTE: Reservations with more than 6 adults will not be accepted.) Pull up and feel relaxed on your Cape Cod vacation. Lounge on the deck with dining table and seating, and grill dinner on the Weber grill. A large yard is great for games and comes with shed to store bikes, boogie boards or other beach gear.brbrThe first floor has a kitchen, dining/living room, bathroom with full tub and shower, along with the main bedroom with 1 queen bed. The second floor has two additional bedrooms, one of the bedrooms has a queen bed and the other bedroom is perfect for the kids having a bunk bed with 2 single beds along with another single bed. There a modern bath in the basement. Overall, the house can sleep up to 8 total, and 6 adults max to be comfortable. NOTE: Any requests with more than 6 adults will not be accepted.brbrThere is also a reading/office loft on the second floor with a desk equipped with a second monitor and hookup for your laptop. There are air conditioning (A/C) split units on each floor (basement, first floor dining area, and second floor hallway) to cool the whole house. Note that the staircases in the home are steep and narrow and typical of a cape cottage built in the 50's.brbrVery quiet and picturesque neighborhood but still close to everything. It is south of 28 and walkable to a number of restaurants and stores in Chatham. You can bike or walk on sidewalk all the way to Hardings Beach via neighborhood cut-through. Hardings Beach is 1.2mi away, Ridgevale Beach is 1.8mi, Schoolhouse Pond is 1.7mi and the Cape Code Rail Trail is only 0.5 miles via bike.brbrWe have rented in Chatham for years and finally decided to get a place of our own so know the area well. Reach out if any questions, recommendations, or issues during your stay.

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$763.31

/ Nightly

Private Vacation Home

Brand New Four Bedroom Home Near Beach and Town

Chatham, Massachusetts, United States

Brand new 4 bedroom, 2 bath North Chatham home near town and beach. On the first floor, the home boasts a designer kitchen, luxury marble bath, and two bedrooms. Upstairs, you will find two very spacious bedrooms with skylights, and another full bathroom. Fully air conditioned. Washer and dryer. Located on a quiet, family-friendly cul-de-sac, our home is the perfect place for your Cape vacation. Chatham Pier, the Lighthouse Beach, Main Street, and the bike trail are within a mile.

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$925.04

/ Nightly

Private Vacation Home

Sweeping Views, 150 Yards to Private Beach!

Chatham, Massachusetts, United States

Summary:brbr16694 - Oceanside Delight: Sweeping Views, 150 Yards to Private Beach!brbrbrbrThe Space:brbrEscape to Oceanside Delight, a five-bedroom haven in the charming town of Chatham, Massachusetts. This seaside retreat located on an acre of private land, accommodating up to 12 guests, offers breathtaking views of Pleasant Bay from its multiple decks, promising a serene getaway with the perfect blend of privacy and proximity.brbrIndulge in the sweeping water views that welcome you from the main living area, adorned with stylish furniture and a smart TV. With three floors, this home provides abundant space for relaxation and rejuvenation. The ground floor features two cozy bedrooms, and a bath, while the first floor boasts a family room with a gas fireplace, two bedrooms, and a large deck for soaking in the ocean breeze. Ascend to the second floor to find one bedroom and a family room complete with a bar and balcony. Take time at the end of the day to enjoy the gaming area in the garage with ping pong, foosball, seating, TV, and bar. brbr Step outside to explore the private beach, about a 10 minute stroll down the private road, or take a quick drive to the town landing beach 1.3 miles from your door. Embrace the outdoors by birdwatching at the nearby pond or simply enjoy the peaceful landscape from your secluded spot on the marshland.brbrVenture out to explore local attractions and dining, with favorites like Chatham Perk and Elwoods Raw Bar just minutes away. Discover the charm of downtown Chatham, where delightful eateries and shopping await.brbrOceanside Delight is not just a place to stay; it's an experience to savor. Whether you seek solitude or adventure, this captivating retreat will fulfill every desire. Book your escape to Oceanside Delight today and create memories that will last a lifetime.brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 12brBedroomsbr-Total 5br-Ground Floor Bedroom: 2 Twinsbr-Ground Floor Bedroom: 1 Full Day Bed with Twin Trundlebr-1st Floor Bedroom: 1 King Bed + 1 Twin Bedbr-1st Floor Bedroom: 1 King Bedbr-2nd Floor Bedroom: 1 King BedbrBathroomsbr-Total 3.5br-1st Floor: ½ Bathbr-1st Floor: Tub and Showerbr-2nd Floor: Full Bath w/ Showerbr-Ground Floor: Tub and ShowerbrOther Amenities br-Central AC via Mini-Splitbr-Smart TVbr-Streaming Servicebr-Washer/Dryer br-Propane Grillbr-Gas Fireplacebr-Please note outdoor amenities are available seasonallybr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-Parking for 4 cars maximumbr-C0526230550br

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$544.78

/ Nightly

Private Vacation Home

Classic Cape House Walking Distance to the Beach - Many recent upgrades

Chatham, Massachusetts, United States

Recent upgrades: Complete interior painted (March 2025); Main dining table refinished (April 2025); Downstairs bathroom remodeled (new tile floor and vanity).brbrClassic cape house, walking distance to Forest Beach, 1 mile to Red River. Beautiful large back yard perfect for enjoying a drink or playing a family game of whiffle ball. Large sun room with comfortable seating and large TV. House has multiple spots to hang out if privacy is desired. 1 bedroom downstairs, 2 bedrooms upstairs. All mattresses, appliances, and outdoor furniture/grill are only *1 year old*.

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$575.35

/ Nightly

Private Vacation Home

FOUR BEDROOM-- CLOSE TO TOWN AND TWO SALTWATER BEACH AREAS!

Chatham, Massachusetts, United States

Enjoy The Loop from this spectacular rental property-- a beautiful two mile walking path boasting spectacular ocean views you're sure to love.brbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbr Just 1 mile to the center of Downtown Chatham and 3/4 of a mile to a saltwater beach (Oyster Pond) offering a popular sandy beach, bathhouse and lifeguard; also, only 1/2 mile to a smaller beach on Sears Point. This charming 4 bedroom, 2 bath home is nicely furnished, well maintained and very comfortable. Property has renovated kitchen with all new appliances. Sit out on the covered porch on wicker furniture-- relax and enjoy the tranquility. The spacious backyard is perfect for barbecues and outdoor sports. It has equal parts shaded and sunny areas to stay cool or get a tan! There are two seating areas in the living room, one end great for television viewing and the other, perfect to relax and enjoy a great book. brbrAll four bedrooms are on the second floor along with a bath with tub and shower. There are two bedrooms with king beds, another bedroom with a queen bed and the fourth bedroom has a queen and one twin bed. There is an additional bath on the first floor with a shower and an enclosed outdoor shower.brbrThis home's kitchen/dining area is bright and sunny, extending the full width of the house to include a seating area and game table. Television in living room has free access to over 350 live TV channels, including news, weather, sports, and more, as well as streaming services (Netflix, Hulu, etc.); via Roku. Property has first floor central air conditioning and laundry, outdoor dining, and four splitter air conditioning units in each of the bedrooms to keep things cool. New gas stove has also been a great addition to the property.brbr Second Floor: Bedroom #1 - King, Bedroom #2 - King, Bedroom #3 - Queen, Bedroom #4 - 1 Double/1 Twin Bedbrbr* Additional fees:br- $175 non-refundable reservation fee (no security deposit required)br- Cleaning Fee - $350br- All applicable taxesbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO SMOKINGbr* OCCUPANCY: 8 (Adults and children)br* PARKING FOR 5 VEHICLESbr* SHEETS AND TOWELS ARE NOT PROVIDED. WE CAN PROVIDE INFORMATION FOR A LINEN RENTAL SERVICE.brbr**** FREE ACTIVITIES INCLUDED ****brTo enhance your vacation experience, Kinlin Grover Compass includes Xplorie, which means free admissions and equipment rentals everyday of your stay at select popular attractions in the area. brbrAs a guest of Kinlin Grover Compass, you'll receive free tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities! Activities and availability are subject to change.brbr**** CANCELLATION/REFUND POLICY ****brUpon cancellation for ANY reason, money will be refunded less a 20% service fee of the total rental amount due, ONLY if the property is re-rented for the same terms and conditions of the original Agreement. Tenant further acknowledges and agrees that where Kinlin Grover Compass undertakes to re-let the property, the rental fee to be charged to the substitute tenant shall be in an amount to be determined in the reasonable discretion of Kinlin Grover Compass and Owner. Tenant agrees that any cancellation of the reservation, undertaken at any time, shall not be effective unless in writing and delivered to Kinlin Grover Compass.

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$682.82

/ Nightly

Private Vacation Home

Stunning Marsh Views, Near Pleasant Street Beach!

Chatham, Massachusetts, United States

Summary:brbr16689: Lady Slipper - Stunning Marsh Views, Near Pleasant St. Beach!brbrbrbrThe Space:brbrNestled in the serene enclave of Chatham, overlooking the picturesque expanse of Red River Marsh, Lady Slipper is the quintessential vacation abode for those seeking unparalleled tranquility. This enchanting retreat, located a mere half mile from the shores of Pleasant Street Beach, offers a panoramic view from its expansive deck, inviting guests to bask in the breathtaking vistas and embrace the coastal allure.brbrBoasting a meticulously designed layout, Lady Slipper features a first-floor master bedroom, ensuring optimal comfort and convenience. The ground floor extends an additional invitation to relaxation with its cozy living room adorned with a Smart TV and queen bed, providing the perfect setting for leisurely evenings with loved ones.brbrStep outside to discover your private oasis, where the sun-drenched back deck beckons for lazy afternoons spent soaking up the coastal rays or hosting vibrant summer gatherings with family and friends. With ample space for everyone to unwind and revel in the joys of vacationing, Lady Slipper promises cherished memories to last a lifetime.brbrBeyond the confines of this charming retreat, adventure awaits at the nearby Pleasant Street Beach, a mere half-mile stroll away, where sun-drenched days and sandy shores await. For those eager to explore further, the idyllic Forest Beach lies just 0.7 miles away, offering an additional haven for seaside escapades.brbrWhen it comes to dining delights, Lady Slipper's prime location ensures easy access to a plethora of culinary treasures. Indulge in a delectable lunch at the nearby Drifters, a mere 0.8 miles away, or embark on a gastronomic journey to remember with unforgettable dinners at Bucas Tuscan Roadhouse, just 0.9 miles away, or Brax Landing, just 1.8 miles away.brbrExperience the epitome of coastal luxury and tranquility at Lady Slipper, where every moment is imbued with the enchanting allure of Chatham's coastal splendor.brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 8brBedroomsbr-Total 4br-Ground Floor Bedroom: 1 Queen Bedbr-Ground Floor Bedroom: 2 Twin Bedsbr-Ground Bedroom: 1 Queen Bedbr-1st Floor Bedroom: 1 Queen BedbrBathroomsbr-Total 2br-Ground Floor: Showerbr-1st Floor: ShowerbrOther Amenities br-Central AC on 1st Floor / Mini Splits on Ground Floorbr-WiFibr-Smart TVbr-Washer/Dryer br-Propane Grillbr-Outdoor Showerbr-Indoor Fireplace is not for guest use(fines remitted)br-Please note outdoor amenities are available seasonallybr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-Parking for 3 cars maximumbr-C0295810550

4

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2

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8

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Vacation Home Rentals By Owner In Chatham, MA

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$544.78

$575.35

$682.82

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