Vacation Rentals By Owner In Chatham, MA

$658.09

Newly Refreshed Upscale Cottage/Pvt 2 KING BR Ensuite /1 Mile to Hardings Beach

Chatham, Massachusetts, United States

Oh Buoy Oh BuoybrbrA Refined Chatham RetreatbrbrEscape to Oh Buoy Oh Buoy, a tastefully renovated Chatham cottage just one mile from the soft white sands and warm waters of Harding’s Beach. Tucked away on a quiet cul-de-sac, this upscale vintage beach home offers a peaceful, polished retreat with all the comforts of modern Cape Cod living.brbrLight-filled and thoughtfully redesigned, the cottage features coastal-inspired interiors, fine furnishings, and brand-new mini-split A/C units in both king bedrooms and the living room. Highlights include a private outdoor deck, a stunning three-season sunroom, a cozy living room with queen pull-out sofa, two king ensuite bedrooms, and a gourmet kitchen with island seating for six.brbrThe home is a sidewalk stroll to local restaurants, charming shops, a bustling harbor with watercraft rentals, and a beloved buy-off-the-boat seafood shanty. Chatham’s vibrant downtown is just two miles away — close enough to enjoy in minutes, yet far enough to return quickly to the calm sanctuary of Oh Buoy Oh Buoy.brbrWhen you choose to stay in, enjoy games and puzzles, high-speed Wi-Fi, Smart TVs in the living room and second bedroom, a cozy electric fireplace (for heat or ambiance), and a propane fire pit on the deck for relaxed evenings under the stars.brbrGuests enjoy full, private use of the entire home. High-quality linens and towels are provided.brbrImportant Notesbr• HOA rules do not allow pets of any kind. Violations result in immediate termination of stay with financial penalties and no refunds.br• Absolutely no smoking permitted.brbrSunroombrbrUpon entering the cottage, guests are welcomed into this casually elegant, quintessentially Cape Cod sunroom. Whitewashed walls, knotty pine ceilings, and a wall of screened sliders create a breezy, inviting space perfect for lounging or entertaining.brbrA vintage tea cart repurposed as a bar offers the ideal spot for cocktails, mocktails, or morning coffee. Sink into the white linen sofa or generous armchair with a book, explore games from the nearby closet, or gather on the chinoiserie bench and director’s chairs for relaxed conversation. In the late afternoon, throw open the doors and let the sea breeze roll in.brbrLiving RoombrbrIf you can tear yourself away from the sunroom, the living room offers a cozy space for movie nights, games, or quiet downtime. Two exceptionally comfortable armchairs (known to induce spontaneous naps), a queen pull-out sofa, a 43-inch Smart TV, and an electric fireplace create an inviting atmosphere year-round.brbrThe fireplace can be used with or without heat, making it perfect for shoulder-season evenings or anytime ambiance is desired. A mini-split A/C unit cools and dehumidifies the space on demand.brbrKing Ensuite Bedroom TwobrbrThis serene retreat blends vintage charm with modern comfort. Crisp white walls and linens, curvy cottage furnishings, original artwork, and whimsical coastal accents set a relaxed tone. The plush king bed is complemented by a private ensuite bath and an individual mini-split A/C unit, allowing guests to tailor their comfort without affecting the rest of the home.brbrAmple storage includes a generous closet, mirrored dresser, and under-bed space — though guests are welcome to pack light thanks to the in-home washer and dryer. The refreshed ensuite bath features a cheerful blue-and-yellow palette, pedestal sink, toilet, and glass-enclosed walk-in shower. (The home is on a private septic system; septic-safe paper is provided.)brbrThe KitchenbrbrOne of the great joys of Cape Cod living is access to fresh, farm- and boat-to-table ingredients — and this gourmet kitchen was designed with that lifestyle in mind.brbrWhether preparing your own meals or working with a local chef, this beautifully appointed space inspires creativity. A six-seat island anchors the room and can be shifted to accommodate prep or seating on both ends. A five-burner gas range with commercial-grade exhaust fan supports restaurant-quality cooking, while the ultra-quiet Bosch dishwasher makes cleanup effortless.brbrAdditional features include a spacious refrigerator/freezer, pantry, lazy Susan, and a built-in beverage station with a Keurig Duo (single-serve or full pot). Take the thermal carafe to the beach and enjoy breakfast by the water.brbrThe kitchen is fully stocked with a wide-slot toaster, microwave, crockpot, electric mixer, mandoline, quality knives and sharpener, blender, generous servingware, premium cookware and bakeware — even specialty tools like an oyster knife and fish scaler. Everything you need to cook… or convincingly plate local takeout.brbrKing Ensuite Bedroom OnebrbrFresh, cheerful, and inspired by Cape Cod’s beloved Marguerite and Montauk daisies, this bedroom offers a bright and calming retreat. A plush king bed is flanked by side tables with storage baskets and adjustable wall sconces for bedtime reading.brbrA mirrored wardrobe provides ample hanging and drawer space, while a cozy wing chair beneath a vibrant floral painting creates a peaceful spot to unwind. A wall-mounted Smart TV is visible from the bed, and a mini-split A/C unit allows for perfectly tuned sleeping comfort.brbrThe refreshed vintage ensuite bath features a glass-door walk-in shower with seating ledge, pedestal sink, and comfort-height toilet.brbrOutdoor LivingbrbrNo Cape Cod getaway is complete without exceptional outdoor living — and Oh Buoy Oh Buoy delivers.brbrStep onto the private, expansive deck designed for alfresco dining and evening relaxation. Enjoy meals at the six-person dining table with umbrella, fire up the gas grill, then settle into Adirondack chairs around the propane fire pit as string lights glow overhead.brbrThe oversized outdoor shower is a true highlight. Rinse off salt and sand beneath the open sky while hummingbirds, butterflies, and hawks drift by. Thanks to the newly installed Rinnai on-demand hot water heater, you can linger as long as you like.

2

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2

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6

Sleeps

$1197.1

/ Nightly

Private Vacation Home

Vacation in the heart of Chatham and walk to everything. Oyster Pond Beach is right around the corner!

Chatham, Massachusetts, United States

Experience downtown Chatham! No need to drive when you can walk to everything. This charming rental features a classic farmer's porch, perfect for relaxing with a drink and a good book. Vacation in the heart of Chatham with easy access to everything, including Oyster Pond Beach, The Chatham Orpheum Theater and The Candy Manor. This beautiful 2-bedroom home is decorated in a modern coastal style, with a king bedroom and a queen and twin bedroom. The bright, airy space features an open first floor and a large kitchen island, ideal for entertaining and relaxing. Enjoy your morning coffee on the spacious back deck before heading to the beach, or use the grill for dinner before an evening movie and ice cream in town. Additional amenities include central A/C, Wi-Fi, streaming services and parking for one car. This rental includes a reusable tote starter pack of cleaning and paper products, compliments of the owner. Call Chatham Rentals today, and let our experienced agents help you plan your perfect stay!

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$505.3

/ Nightly

Cottage

Sarah-N-Dipity: Cozy Cottage Near Ridgevale Beach

Chatham, Massachusetts, United States

2 Bedrooms - 1 Bathroom - Sleeps 4brA 3-night midweek stay - Monday to Wednesday - is offered at this home during the peak season. Off season calendars offer more flexibility.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-OutbrbrWelcome to Sarah-N-Dipity! Pet Friendly, 2 bedrooms, 1 bathroom cottage. Located in a private Chatham neighborhood and just a short walk to Ridgevale Beach! AC, WIFI and outdoor living area overlooking the marsh and Cockle Cove Creek.brbrOwners Share Why I Love My Home:brWe enjoy early morning coffee on the deck, taking in what nature has to offer without leaving the house, and stargazing at night. With the ocean less than a 10-minute walk, it's a wonderful beach escape. We hope you enjoy it as much as we do!brbrLet Us Tell You About This Home:brCustom Rental Week - this home is available in season for a Monday arrival and Thursday departure. Enjoy a mid-week staybrbrEnter this bright and updated cottage directly into a well appointed kitchen. You'll have use of all the appliances you need to make family dinners and a large double farmer's sink for washing dishes (this home does not have a dishwasher).brbrTo your left, up two stairs, is the open and contemporary dining /living area with slider access to the large outdoor living space. In the living room there are two cozy couches that face the beautiful gas fireplace.brbrBoth bedrooms are at the front of the house along with the full bathroom with tub shower combo. The main bedroom is well appointed with a queen bed, dresser and large closet. The second bedroom has a full over full bunk bed, dresser and open shelving with games and books to entertain on your vacation. brbrThe outdoor living space features a marsh view with a large outdoor dining table and chairs, outdoor couch, and propane fire pit. The outdoor space also features a patio area, a large outdoor shower and plenty of space to play or relax. brbrStay at Sarah-N-Dipity for a Cape Cod experience with a perfect marsh view. brbr*This home does not provide a washer / dryer. If you need laundry service, we recommend Star Laundry in Dennisport.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).brThis home has Keyless Entry for your convenience.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: 4 - No parking on lawn anytime. brbrAdditional 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. brbr***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.** brbrOur 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 Info: *Mileage is approximatebr0.3 mile to Ridgevale Beachbr1.3 mile to the best homemade ice cream at Short and Sweet!br1.5 mile to the Bike trail from Route 137 - More info on The Rail Trail can be found here: Info on Cape Cod bike trailsbr1.5 mile to Kream N Kone - fried seafoodbr1.7 mile to Larry's PX - have breakfast with the localsbr1.9 mile to Pisces Restaurant - fine dining (be sure to book a reservation!)brbrShort drive ( 3.4 miles) into the town of Chatham where you will find :brThe Orpheum movie theaterbrSeal toursbrShoppingbrRestaurantsbrFriday night bandstand concertsbrThe Monomoy TheaterbrPlaygroundbrPublic TennisbrChatham A's Baseballbr*Mileage is approximate

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$691.28

/ Nightly

Private Vacation Home

Luxury Chatham Retreat. Walk to Main St & Beach

Chatham, Massachusetts, United States

Ditch the car and dive into the quintessential Chatham lifestyle. Perfectly situated, this impeccably designed 2-bedroom, 3-bath retreat offers the luxury of total walkability. Whether you’re strolling to Main Street for your morning pastry, hitting the bike path for a scenic ride, or relaxing by the gas fireplace after a day at the beach, this is your sophisticated home base for the ultimate Cape Cod escape. High-end finishes meet coastal comfort in a space designed for effortless memories.brThe spacebrThe Living Experience:brThe heart of the home features an open-concept layout with high-end finishes throughout. The gourmet kitchen is fully equipped for everything from quick breakfasts to elaborate seafood dinners. In the evening, retreat to the living area to enjoy the warmth of the cozy gas fireplace and curated coastal decor.brbrLuxury Suite Accommodations:brDesigned for privacy and comfort, our home features two distinct suites:brbrSuite 1 (The Primary): A serene sanctuary featuring a Queen bed with premium linens and a relaxing vibe.brbrSuite 2 (The Bunk Suite): The ultimate flex space. Purpose-built to sleep 4, it features a sturdy bunk bed plus two Twin XL beds, perfect for kids, teens, or adults needing extra legroom.brbrPrime Walk-to-Everything Location:brForget the stress of Cape Cod traffic. You are truly steps away from:brbrMain Street: Chatham’s iconic shops, fine dining, and local bakeries.brbrAdventure: Directly adjacent to the legendary Bike Path (Bike rentals are just a stroll away!).brbrConvenience: Grocery stores and pharmacies are within a 5-minute walk.brbrThoughtful Touches:brWe pride ourselves on an impeccably clean home. You'll find the pantry and baths thoughtfully stocked with the essentials so you can start your vacation the moment you walk through the door.

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$507.41

/ Nightly

Private Vacation Home

Cozy Chatham home with privacy and nautical decor

Chatham, Massachusetts, United States

Retreat to the heart of Cape Cod in this restored Cape salt box cottage with 2 bedrooms, offering 1 queen and 2 twins. Starry Hill Cottage combines elements of old Cape Cod with modern finishes and decor. Located atop a grassy hill and set back from the road, this property offers privacy and includes a fully stocked kitchen, light-filled spaces, cottage gardens, outdoor shower, barbecue grill, central AC, WiFi, Smart TV, and an outdoor deck suitable for enjoying morning coffee. Whether you want to relax surrounded by heritage oaks and maples, spend time in town, or visit the beaches, Starry Hill is conveniently situated. The location is a five-minute drive from Main Street Chatham, which has dining, shopping, coffee and wine bars, and access to Route 28 for coastal drives up to Orleans and the Upper Cape. Within less than five minutes' drive you will find beaches, trailheads, swimming ponds, and more. Dog Friendly! 1 dog allowed. Ask your agent for details. This home comes with a Welcome Bag: a reusable tote filled with paper and cleaning supplies compliments of the owner. Call Chatham Rentals today!

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$433.98

/ Nightly

Private Vacation Home

Great Location Outdoor Space Dog Friendly

Chatham, Massachusetts, United States

Summary:brbr16601 - The Salty Seashell: Great Location Outdoor Space Dog FriendlybrbrbrbrThe Space:brbrSet in Chatham, this well-appointed Cape Cod home offers an easy, comfortable base for classic Cape days—from morning walks to Hey Joe & Jam for coffee, to afternoons at Harding’s Beach or Oyster Pond, and evenings spent back at home unwinding together. With classic details and practical amenities, it’s a place that feels relaxed from the moment you arrive.brbrThe main living and dining areas feature wide-plank pine hardwood floors and a flat-screen TV, perfect for winding down after a day at the beach or watching a game at Veterans Field. The fully equipped galley kitchen includes a gas stove, dishwasher, and large side-by-side refrigerator—ideal for everything from quick breakfasts or family dinners.brbrOn the main floor, you’ll find a bedroom with a queen bed along with a full bathroom. Upstairs, two additional bedrooms—one with a queen bed and a twin with a trundle (2 twin beds), the other with a queen bed and a twin bed—share a comfortable loft area with new furniture that works well as a secondary lounge or kids’ hangout. The private primary suite, located on the second floor above the garage, is accessed from within the home via its own staircase and features a king bed and an updated en suite full bathroom.brbrOutside, the backyard offers space to relax and play, with a fire pit and Adirondack chairs set up for easy evenings outdoors—perhaps after ice cream at Kream & Kone or a sunset walk around town. Sliding glass doors from the kitchen and dining area lead to the deck and adjacent patio, creating a convenient flow for grilling, outdoor meals, or stepping outside with your morning coffee. A ping-pong table in the basement adds indoor entertainment for rainy days or active evenings.brbrWhether you’re staying close to home or heading out to explore everything Chatham has to offer, this is the perfect place to settle in.brbrHome Details: br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 10br-2 floorsbrBedroomsbr-Total 4br-1st Floor Bedroom 1: 1 Queen Bedbr-2nd Floor Master Bedroom: 1 King Bed w/ en suite Full Bathroombr-2nd Floor Bedroom 1: 1 Queen Bed and 1 Twin Bed w/ Trundle (2 Twins)br-2nd Floor Bedroom 2: 1 Queen Bed and 1 Twin BedbrBathroomsbr-Total 3br-1st Floor: Full Bathroom w/ Showerbr-2nd Floor: Full Bathroom w/ Shower/Tub combobr-2nd Floor: Full Bathroom w/ Shower/Tub combo (en suite King Bedroom)brOther Amenitiesbr-WiFibr-TVbr-Central A/Cbr-Washer/Dryerbr-Indoor Fireplace NOT for guest use (fines remitted)br-Gas grillbr-Outdoor showerbr-Fire Pit (wood)br-Private yardbr-Ping Pong Table in Basementbr-Minutes to the beachbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-Parking for 3 cars maximumbrC0423810550brbrbrbrThe Neighborhood:brbrOceanside

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$606.36

/ Nightly

Private Vacation Home

Enjoy Classic Chatham Charm and Easy Stroll to Downtown!

Chatham, Massachusetts, United States

brbrClassic Chatham home, recently remodeled, located in the heart of the village and just steps to Mill Pond! It features comfortable furnishings, and a completely renovated kitchen with sparkling appliances and renovated bathrooms. Enjoy what Chatham has to offer from the best location in town. Walk to Lighthouse Beach for a gorgeous day at the beach, and take advantage of the many upscale restaurants on Main Street. Relax on the front porch after a long day at the beach or boating on Mill Pond and then it is a quick stroll for shopping at some of the finest stores on Cape Cod. This rental is perfect for the smaller family looking to experience the best of Chatham!brbrbr5 A/C Units, Gas Grill, Enclosed Outdoor Shower, Wireless Internet and 1 TV in Living Room

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$872.43

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Private Vacation Home

Steps to Chatham Center & Lighthouse Beach - charming home with central AC

Chatham, Massachusetts, United States

Steps from Chatham Center and a short walk to Lighthouse Beach, our home is the perfect spot for families and couples looking to enjoy all that Chatham has to offer. brbrWith three bedrooms and four full bathrooms, our centrally air-conditioned home comfortably sleeps six people. The house has two living room areas - with plenty of space to spread out, play games, read a good book or watch the large flat screen TV. The kitchen has a granite counter breakfast bar and dining table. It is fully equipped for all your needs with new stainless steel appliances, drip coffee maker, keurig, toaster, blender, lobster pot and outdoor grill. brbrA lovely sunroom dining area is the perfect space for family meals. A backyard patio and second floor deck provide additional space for relaxing in the sunshine and enjoying the Cape Cod sea air. An outdoor shower is conveniently located outside the side entrance to the home.brbrThe primary bedroom (king bed), two full bathrooms and laundry room are on the first floor, with two additional bedrooms (one queen, two twins) and two full bathrooms on the second floor. There are flat screen TVs in the living room and in the primary bedroom. Free WiFi is also provided for our guests.brbrJust steps from town, guests can enjoy all that Chatham Center has to offer without getting in the car. Shops, art galleries, bookstores, parks, cafes and restaurants - and so much more!brbrA very short walk away from town, guests will find Lighthouse Beach - a beautiful Cape Cod beach and lighthouse that are not to be missed.brbrLinens (bed sheets and bath towels) are included. Six beach towels will also be included for your convenience. brbrParking is available for maximum of three cars. No smoking of anything containing tobacco, any other substance, and e-cigarettes, inside or outside of the home.

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Select Dates for Price

Private Vacation Home

Awesome Location! Right on the Chatham Loop, Perfect for Long Walks!

Chatham, Massachusetts, United States

Awesome Location! Right on the Chatham Loop, it is Perfect for Long Walks!brThis 4-bedroom Cape House is close to town and beaches with great outdoor spaces, & views over conservation woodlands. Access to Chatham's Downtown shops, galleries, and restaurants is a short stroll away. Oyster Pond Beach (no beach parking sticker required) is also a short distance away and is a great swimming hole, especially for young kids, with lifeguards, and excellent restrooms. The majestic Chatham Light and the picturesque Atlantic-facing sands of Lighthouse Beach are about 1 mile from the doorstep of this vacation rental home. Entertain with friends and family with this great room (kitchen, dining, and living) concept. On cool summer nights enjoy cocktails in the bug-free three-season screened-in sun-room too...this home is well-outfitted for any summer stay!

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$711.93

/ Nightly

Apartment

Beautiful Downtown Chatham 1 Bed, Close to the Beach - Newly renovated + Patio

Chatham, Massachusetts, United States

This gorgeous home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, restaurants, the beach, movie theater, Veterans Field for summer Chatham A’s games & more! This cozy apartment is perfect for a couple or two friends with an open living room, kitchen/dining area, and private patio. This apartment has been completely renovated from head to toe - from new stainless steel appliances to hardwood floors, and nautical accents. Please know, there is no onsite parking. There is a free public parking lot across the street, to the right of the Red Nun restaurant. There are two outdoor security cameras for added security, one at the exterior of front door and the other at side door exterior.brbr4 Min Walk to Downtown Chatham br9 Min Walk to Oyster Pond Beach brbrExperience Chatham with us & Learn More Below!brbrKEY FEATURES:br☀ Sleeps 2; 1 bedroom, 1 queen br☀ 1 full bathroom br☀ Open concept living room and kitchen br☀ Modern, quality amenitiesbr☀ Well-equipped kitchen with countertop seating br☀ Outdoor Patio br☀ Smart TVbr☀ Comfortable and Stylish design br☀ Newly renovated - everything is brand new br☀ 1-10min walking distance to downtown Chatham, shops, restaurants, bars CVS, supermarket, bakeries, coffee shops, liquor store and more br☀ A/C brbrHere Are A Few Kind Words From Our Past Guests:brbr“Loved it, really enjoyed staying here. It was very clean and easy. This place has everything you need” - Tim brbr“It's the perfect location to explore the Cape. Lois is a wonderful host, and it was a perfect weekend!” - Nikolas brbr“Amazing! Very centralized location, walkable to the beach and great restaurants. The cottage is impeccable and feels brand new. Clean, functional and very “cape cod” design. I love the fact that it features great quality items from utensils to bedding, glassware and everything in between!” - Rayra brbr☆☆ BEDROOM ☆☆brbrThis immaculate apartment has 1 bedroom fitted with a queen-sized bed made up with beautiful white bed linens and en suite bathroom. brbr☆☆ BATHROOM ☆☆brbrThere is one full bathroom off of the bedroom. brbr☆☆ KITCHEN & LOUNGE ☆☆brbrThe kitchen, living, and dining area has an open concept floor plan, great for socializing while cooking in the kitchen, dining at the counter, enjoying morning coffee or sipping evening drinks before dinner. A coffee machine and coffee is included. brbrThe living room area has a cozy couch and large chair with a smart TV. The dining and kitchen area has two bar stools at the counter. There is also a small private patio outside with a seating area. brbrOriginal paintings of Chatham throughout the house by local Chatham Artist, Lois Castellana. brbr☆☆ OUTSIDE SPACE ☆☆brbrThe exterior area of this home has a small patio with two Adirondack chairs. Perfect for sipping your morning coffee, a glass of wine, a cocktail or just relaxing. brbr☆☆ PARKING ☆☆brPlease know this property does not have on-site parking. There is a public parking lot across the street to the right of the Red Nun restaurant and a public parking lot downtown Chatham, within a 5 minute walk. If the Main house right next door is not rented at the time of your stay, you will have parking onsite, I will not have this information until the day you arrive.brbr☆☆ HOUSE RULES ☆☆brbr- No events or parties.br- No more than 2 guests max allowed at the home, unless given prior approval (for young kids only).br- No pets.br- No smoking.br- Quiet hours: 10pm-8ambr- No food or drink other than water in the living areas or bedrooms.br- Must be 25+ years old to book.br- This is a private family home, please be respectful.brbr☆☆ WHEN REQUESTING TO BOOK ☆☆brbrPlease share a bit about yourself - what brings you to Chatham, who you are traveling with, and how many people will be staying at the property.brbr★★★ Book Today & Let Us Take Care Of You In Chatham! ★★★

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$556.19

/ Nightly

Private Vacation Home

Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball

Chatham, Massachusetts, United States

Renovated year round 4 bedroom house with bonus office/bunk room with central AC, walking distance to downtown Chatham. Beautifully decorated for your Cape Cod beach vacation with extended family or friends. Excellent setup for families with kids with bunk beds and playroom in lower level. Enjoy the back deck and grill overlooking beautifully landscaped private yard and gardens with new outdoor shower (seasonal). Walk or quick drive to top rated, popular restaurants (Del Mar, Red Nun, Chatham Squire), markets (Village Market and CVS), shops (too many to name!) and picturesque beaches in every direction (closest to Oyster Pond). Street has direct access to the Cape Cod Rail Trail, Bike Path and tennis/pickleball courts. Linens now included!brbrThe Space:brBright, airy living/dining space opens to updated, well-appointed kitchen with brand-new stainless-steel appliances and white cabinets. Living room has electric fireplace, Smart TV (Roku) and high-speed internet connectivity.brMain level has master bedroom with king bed and master half bathroom, corner bedroom with queen bed and third bedroom with another queen bed and small desk. This level also has a full bathroom with tub.brLower level has playroom/game room with seating area, futon for one person and another Smart TV. There is also bonus room with bunk beds for kids or this room can be used as an office. There is a washer dryer and garage for storing beach gear and bikes.brThere is a large deck with dining table and landscaped, private backyard with outdoor shower. brHouse has parking for up to 3 cars and is on a quiet, peaceful street very close to everything Chatham has to offer! Enjoy the Chatham Fish Pier, Lighthouse, 4th of July parade, Chatham A’s baseball games, band concerts or First Night fireworks. Close to Chatham Bars Inn (1.8 miles) or the Wequassett Resort and Golf Club (3.4 miles).brThings to Note:brPillows and comforters are provided for every bed. brNew for 2025! We are excited to include linens provided by Chatham Concierge for your comfort and convenience. Enjoy hotel-quality, high thread count luxury sheets and towels, all professionally cleaned using hypoallergenic, eco-friendly organic products. The linens are processed locally using the most energy-efficient laundry equipment available. Bed making is included as part of the cleaning fee, and we also provide beach towels in season for your enjoyment.brSorry, no pets are allowed.

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$791.62

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Private Vacation Home

Unique Oyster Pond 3bd-2ba home in private setting close to downtown.

Chatham, Massachusetts, United States

STEPS FROM OYSTER POND, SHORT WALK TO TOWN AND CAPE LEAGUE BASEBALL GAMES! This truly is a unique beach house in an exclusive and quiet location just steps from Oyster Pond. Property is very clean and bright and well maintained. This 3-bedroom, 2-bath home with open floor plan, cathedral ceilings and finished basement is located on a quiet lane and is just 9/10's of a mile to the Chatham Angler's ball-field, and just a bit farther to beaches and downtown. Air conditioning, wireless internet access, first floor laundry, enclosed outdoor shower, SoloStove patio with Adirondack chairs, and Weber gas grill. Master king bedroom has private bath and balcony.br* Bed Linens Providedbr* Bath and Beach Towels Provided for Conveniencebr* Beach Chairs, Coolers, etc. Provided for Convenience

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$801.15

/ Nightly

Private Vacation Home

Charming Family Cape, Impeccably Landscaped With Water Views Near The Beach!

Chatham, Massachusetts, United States

Cozy and quiet 3 bedroom, 2 bath Cape style home with an expansive, beautifully landscaped yard…the largest in the area. You'll enjoy picturesque views of the water, easy access to the beach, and a large, 2-level deck for relaxing, grilling and entertaining as well as a custom outdoor shower built over a bluestone floor. Located in a quiet residential neighborhood with almost no traffic, you are minutes away from the beach, downtown, the Cape Cod bike path, Harwichport and some of the top rated restaurants on the Cape.

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$486.91

/ Nightly

Private Vacation Home

Short Walk to Beach From Clean, Beautiful 3BR/2BA Home!

Chatham, Massachusetts, United States

Pretty, completely renovated 3BR home on quiet cul de sac, located w/in a 5-10 minute stroll to beautiful, family-friendly Ridgevale Beach. Wireless Internet/TV/phone w/movie channels. Great kitchen w/all appliances & cooking tools incl. Lg. new deck overlooks treed conservation land. Huge bedrooms w/newer, comfortable, clean beds, sitting chairs, & all linens incl.; 2 queen beds, 2 twin beds. Sleeps 6. Washer/dryer avail. Central A/C. Drive 5 minutes to charming Chatham Square for great shopping, ice cream, coffee and restaurant delights. Enjoy early a.m. or p.m. walks filled with amazing sunrises/ sunsets, salty air smells, and brilliant views! Close to bike path, beautiful beaches, golf courses, nature trails & many local Cape Cod activities. See the stars, smell the salt air, and taste the best foods the Cape has to offer. Feel the gentle ocean breezes on your face, and say to yourself, “I am so grateful I chose Ridgevale Heights!'brbrbr8 minute Walk to Ridgevale Beach: Ridgevale Ave is the main road to Ridgevale Beach, and Shannon Lane is located off of Ridgevale Ave. conveniently south of Rte 28, which means there are no busy streets to cross over in order to walk to the beach. The beach is just under .5 miles from our home, which takes about 10 minutes to walk on average. It's a pleasant neighborhood filled with pretty homes. Popular for families, Ridgevale Beach is unique in that there is an inlet where children can swim and play in more shallow water. Adults can enjoy swimming in the Atlantic ocean opposite this inlet. There is lifeguard patrol, as well as outdoor bathroom facilities, a small snack diner and public parking managed by the town. This beach is beautiful, with sandy shorelines and ample shoreline space for short walks along the beachfront.brbrOur home is also within a 3 miles of a few other beautiful Chatham Beaches, accessible by car: Forest Beach, Hardings Beach and Cockle Cove. Small fresh water ponds are also nearby.brbrPlease note that reservation requests during peak season (June, July and August) must be from Saturday(s) to Saturday(s).

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$1951.01

/ Nightly

Private Vacation Home

Enjoy a Cape Cod beach vacation on the beach in picturesque Chatham.

Chatham, Massachusetts, United States

Have the vacation of your dreams in this oceanfront beach cottage with beautiful water views, located on Morris Island in Chaham Cape Cod. Brand new construction with spectacular interiors. Includes a fully appointed kitchen and wrap-around deck. The master has a king bed and there are two twin beds in the second bedroom as well as two twin beds in the den.brbrTown of Chatham permit STR-322.

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2

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6

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$1119.16

/ Nightly

Private Vacation Home

Do Not Use This Version: Lovers Lake

Chatham, Massachusetts, United States

Discover the perfect blend of family adventure and serene “work-from-home” luxury at this stunning 3,100 sq. ft. Lovers Lake retreat—a private waterfront home created for relaxed mornings, shared meals, and time well spent together. Completely renovated with a modern coastal aesthetic, this one-floor living home offers beautiful water views from every room and a peaceful setting designed for relaxation and connection.brbrTHE LOVERS LAKE EXPERIENCE brLocated on a quiet, private community lake, the water truly becomes your backyard. Lovers Lake is a freshwater, non-motorized lake, ideal for swimming, paddling, and enjoying nature without the noise or crowds of public beaches. Morning swims, paddle outings, and peaceful afternoons by the water make it easy to settle into a slower, more relaxed rhythm.br• Private Dock: Step directly from the lawn onto your private dock for a morning swim in the clear, calm waters. br• Lake Adventures: Explore the shoreline with the provided paddleboat, canoe, and stand-up paddleboard (SUP). br• Privacy: Set on nearly an acre of secluded land, the home feels worlds away from the bustle while remaining just minutes from downtown Chatham.brbrSPACE FOR THE WHOLE FAMILY brWith 4 spacious bedrooms and 3 full bathrooms—plus an outdoor shower—there’s plenty of space for everyone to spread out comfortably.br• Primary Suite: A private retreat featuring a soaking tub and a separate walk-in shower. br• The “Windmill” Family Room: A favorite with kids—this separate circular wing is perfect for movie nights, games, and cozy downtime. br• The Living Room: The main adult gathering space, furnished with high-end seating and equipped with a Bose SoundDock and FM radios to set a relaxed mood. br• Chef’s Kitchen: Well-equipped for family meals, with cookware, dishware, glassware, and a Keurig for morning coffee. The dining table comfortably seats eight.brbrDEDICATED REMOTE WORKSPACES brDesigned with today’s travelers in mind, the home includes two quiet, dedicated workstations, thoughtfully positioned away from the main living areas.br• Tech-Ready: One workstation includes an external monitor. br• Connectivity: Powered by T-Mobile 5G Internet, providing reliable speeds for video calls, streaming, and remote work.brbrOUTDOOR LIVING & EVENINGS brThe expansive mahogany deck is an outdoor oasis. Grill your favorites on the gas BBQ and dine al fresco at the large patio table. In the evening, enjoy the calm Cape Cod atmosphere at the outdoor fire pit—perfect for quiet conversation, stargazing, and unwinding together after a full day on the lake.brbrESSENTIAL DETAILS br• Configuration: 4 Bedrooms / 3 Bathrooms (one-floor living) br• Rental Schedule: Saturday-to-Saturday weekly rental br• Linens: Optional linen package available for your convenience br• Management: Professionally managed locally, with many families returning year after year. brLovingly maintained and thoughtfully updated over many years, this home has welcomed returning families season after season.

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$419.65

/ Nightly

Private Vacation Home

Beautiful Retreat / Hot tub/ Walk to Ridgevale Beach

Chatham, Massachusetts, United States

Lovely, sun-filled, completely renovated, 4 bedroom 2 full bath house located within walking distance to beautiful, kid-friendly Ridgevale Beach. This comfortable home features a private expansive deck with seating for 10, Outdoor shower, relaxing hot tub, heated bathroom floors, brick wood-burning fireplace, a/c units in all bedrooms, beautifully landscaped grounds, and exquisite New England décor.brThis picturesque kid and pet friendly home promises a charming and relaxing year-round stay.

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$2362.78

/ Nightly

Private Vacation Home

The Barn at Chatham Oaks

Chatham, Massachusetts, United States

Experience the ultimate getaway at this stunning 7-bedroom retreat, just a mile from Cape Cod’s pristine beaches. Enjoy a top-rated gourmet kitchen, a charming renovated barn, and a Catina Pool Bar perfect for poolside relaxation. With a sparkling pool and a soothing sauna, this home offers the perfect blend of elegance and comfort. This property is ideal for family vacations, group getaways, and special celebrations. Book now brbrNo events allowed. brbrFeel free to reach out with anything you need.brbrOur home is perfectly situated for you to experience the best of Cape Cod. Pristine beaches are just a mile away, offering easy access to sun, sand, and surf.brbrFor outdoor enthusiasts, the Cape Cod Rail Trail is directly across the street, ideal for scenic bike rides and walks. You can also catch a Chatham A's baseball game, with the field located just five minutes up the road.brbrGetting AroundbrA car is recommended for exploring the wider Cape Cod area, and the property offers ample parking. Biking is also a fantastic way to get around locally, with the convenient rail trail right at your doorstep.brbrYou will have private access to the entire property, including the main house, barn, pool, hot tub, and grounds. Entry is seamless with a secure door code, which will be provided to you before your arrival.brbrWelcome to Coastal Bliss, your ultimate 7-bedroom Cape Cod retreat, recently featured for its style and entertainment value on Season 3 of CBS’s Staycation! Perfect for family vacations and group getaways, our property offers a stunning blend of coastal luxury and comfort.brbrInside the main house, unleash your inner chef in the gourmet eat-in kitchen, named one of the top kitchens on Cape Cod by WNAV. The home also features a dedicated workspace for those needing to stay connected during their getaway.brbrDiscover the unique charm of the renovated barn, a separate space with vaulted wood ceilings, a cozy sectional sofa, and its own kitchenette—perfect for quiet moments or small group gatherings. For entertainment, the lower-level 'Cantina' game room comes complete with a bar, a ping pong table, and direct walk-out access to the pool deck.brbrStep outside to your private oasis. Dive into the sparkling pool, mix cocktails at the Catina Pool Bar, or unwind in the private hot tub. For ultimate relaxation, soothe your muscles in the luxurious, wood-paneled sauna. Our home is proudly pet-friendly, so your furry family members are welcome to join the vacation.brbrAccommodations With 7 beautifully appointed bedrooms, our property provides comfort and tranquility for your entire group.brbrMain House:brBedroom 1: King bed with en-suite bathroombrBedroom 2: Twin-over-twin bunk bedbrBedroom 3: Twin-over-twin bunk bedbrBedroom 4: Two (2) full bedsbrBarn:brBedroom 5: Queen bed (first floor)brBedroom 6: Full bedbrBedroom 7: Full bed

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Select Dates for Price

Private Vacation Home

Charming ranch on quiet road.

Chatham, Massachusetts, United States

This sunny, cozy Cape-style ranch is a short driving distance to both Harding's and Oyster Pond beaches and the quaint village of Chatham. This charming home has easy one level living with a queen master bedroom and a guest bedroom with two twins. Each bedroom has a window a/c unit and WiFi. Enjoy sipping your coffee on the sunny deck, and rinse off the sand from the beach in the great outdoor shower. Welcome bag included compliments of the owner-reusable bag filled with cleaning and paper products. A perfect spot for your family's vacation! Call us at Chatham Rentals and let us help you plan your stay.

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$392.5

/ Nightly

Condo

Steps to Private Association Beach. End Unit Condo at Outermost Harbor.

Chatham, Massachusetts, United States

Updated Condo at Outermost Harbor. Enjoy amazing views of the famous Chatham sandbars or catch a glimpse of playful seals by the Marina from the private association beach. Take a lovely 1/4 mile walk through the dune pathway along the sandbar to Lighthouse Beach or to Monomoy Wildlife Refuge. Located steps away is the Outermost Marina (a Freedom Boat Club host) that offers shuttle service to North and South Beaches and seal tours. Take a pleasant one mile walk to town to visit the many shops and restaurants including the Chatham Squire, Wild Goose Tavern and Impudent Oyster, or stay put and enjoy the beautiful sunrise over the ocean while sipping coffee on a rocker outside the front door. If not an early riser, you can take in a beautiful sunset while grilling and sipping a cocktail or just relaxing on the private back deck that is equipped with an Adirondack dining table and outdoor sofa. The Chatham Bars Inn and all its restaurants are approximately 1 mile away and just beyond that is the famous Chatham Fish Pier with delectable fresh and cooked seafood. The viewing deck is a great spot to watch the local fishermen bring in the day's catch and to observe the seals swimming about. This end unit with its large windows providing natural light and wonderful views is truly a fabulous location in which to explore Cape Cod. brbrEnjoy the newly renovated kitchen with counter seating for meals and the living area with reclining sofa and chairs to enjoy a movie night. The primary bedroom is located on the main level and has a queen size bed, closet, dresser and stackable washer and dryer with a slider to the deck. The loft has a full size futon with dresser and work area. Behind a barn door in the eaves, is a cozy sleep nook with a full size bed, dresser and small TV. brAccommodation for 4 guests only.brBath and bed linens are included

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