Vacation Rentals By Owner In Chatham, MA

$558.45

PERFECT RENOVATED CHATHAM RETREAT! CENTRAL AC, COMFORTABLY SLEEPS 6!

Chatham, Massachusetts, United States

Check in to this beautifully renovated West Chatham ranch, located south of 28 on a quiet cul-de-sac perfect for families to relax and unwind after a day at one of Chatham's many pristine beaches. Located 1 mile from Ridgevale Beach and walking distance to many of the local amenities, restaurants, and shops. The bike rail trail entry is .2 miles away and 2 miles from downtown Chatham. brbrThe open concept home features vaulted ceilings and a fully equip stainless steel/granite kitchen with 4 seat breakfast bar. The patio hosts a Weber gas grill with a large table for 6 plus two loungers. The dining room table seats 4 with a leaf for 6. brbrThe home offers a king bed in the master bedroom with an ensuite. There are two extra bedrooms, one with a queen bed and the other with a full/twin bunk bed and trundle. brbrA partially finished basement with sectional, wall-mounted flat screen, office, and laundry room allows for a separate living area. brbrNote: Linens and towels are not provided, but are available for rental locally with delivery included. Or, we can provide linens for an additional fee.brbrAmenities include:br- wifi by Xfinitybr- central ACbr- cable television by Xfinitybr- Keurig coffee makerbr- 4 smart tv's (1 master bd, 1 guest bed, family room, basement)br- pack-n-playbr- high chair & booster seatbr- outdoor shower/changing areabr- washer/dryerbr- dishwasherbr- weber 4 burner gas grillbr- patio table (seats 6)br- 2 loungersbr- garagebr- coolers, bikes, beach toys, umbrellas, and chairs to bring to the beach

3

Bed

2

Bath

6

Sleeps

$1688.25

/ Nightly

Private Vacation Home

Great Location Steps to Chatham Lighthouse & Town

Chatham, Massachusetts, United States

brbrPRICE RECENTLY REDUCED BY $2500! brStunning four-bedroom home located in the heart of Chatham...tucked away in the Old Village section of town, you can walk to everything! brbrAll that downtown Chatham has to offer, including the shops, ice cream, restaurants, and the summertime Friday Night Band Concerts, are only about a 1/2 mile stroll down picturesque Main Street. Take a short walk in the opposite direction, and find yourself right at Lighthouse Beach...the best of both worlds! This gorgeous home offers a spacious open floor plan on the main floor, with new living room furniture, that opens up to a large deck and screened-in porch, great for a bug-free evening. It features a Queen en-suite primary on the first floor and an en-suite King bedroom on the 2nd floor. The second-floor en-suite bedroom also has a Twin Trundle, and there are two more bedrooms and a full bath. Downstairs in the lower level, you will find more living space and two bunk beds, perfect for the kids, as well as another full bathroom. Take advantage of the huge backyard, with plenty of room for outdoor games and lounging in the sun after a busy day. This is the spot for you!

Bed

Bath

Sleeps

$452.36

/ Nightly

Private Vacation Home

Sun Room Beaches and Dog Welcome!

Chatham, Massachusetts, United States

Summary:brbr16649 - Sunny Skies: Sun Room Beaches and Dog Welcome!brbrbrbrThe Space:brbrFrom your doorstep, take a stroll, bike ride, or a 3 minute car ride down to Forest Beach to enjoy some of the most beautiful white sand on Cape Cod! This location is a prime spot for beach hopping; Cockle Cove, Hardings Beach, Forest Beach, Ridgevale Beach, and Red River Beach are all under 10 minutes from the home, so you’ll never run out of spots to relax in the sun. Access to the Cape Cod Rail Trail bike path is right next to the home, and just a minute or two ride will bring you to Short and Sweet for some delicious ice cream, no need to find parking. If you’re seeking something more substantial, Mom & Pops Burgers, an amazing lunch & dinner option is just down the street as well. Visit downtown Chatham, or Harwich Port, both nearby for all your shopping and activities.br br Entering the home, you’ll find a sun-drenched living area/dining area separated by stairs leading to the second floor. Behind the stairwell is the kitchen, with an eat-in option, and doorway opening to the dining area for easy serving. The hallway on the first floor has a full bathroom and leads to a bedroom with a queen-size bed. Upstairs offers an additional bathroom, and two more bedrooms, one with a queen-size bed, and the other with two twin beds - perfect for the kids. A newly added sunroom allows you to enjoy summer nights bug-free and comfortable, the perfect place to relax during your Cape stay. brbrOutside, a large backyard has plenty of space to play and enjoy the outdoors, and the end of this road is very quiet and peaceful. The location of this home is fantastic and is a great option for visiting two different towns very close together (Chatham and Harwich). The access to the bike path and several gorgeous beaches provides ample options to explore and enjoy everything Cape Cod has to offer!brbrbrHome Details:brbr-Dogs Welcomed (w/fee of $45/night per dog)brbr-Sleeps 6brbr-2 Floorsbrbr-1st Floor Master Bedroom: 1 Queen Bedbrbr-2nd Floor Bedroom #1: 1 Queen Bedbrbr-2nd Floor Bedroom #2: 2 Twin BedsbrBathroomsbr-Total: 2br-1st Floor: Full Bath w/ Showerbr-2nd Floor: Full Bath w/ Showerbr-Central AC (1st Floor)br-Window A/C Units in Bedroomsbrbr-WiFibrbr-Smart TVbrbr-Cablebrbr-Washer/Dryer in Basementbrbr-Walk to Bike Pathbr-Private Yard w/ Lawn Furniturebr-Propane Grillbr-Beach Chairsbr-1 Mile to the Beachesbr-1/2 Mile to Restaurantsbr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0404140550brbrbrbrThe Neighborhood:brbrOceanside

Bed

Bath

Sleeps

$1793.05

/ Nightly

Private Vacation Home

Chatham Loop/Stage Neck/5 Bed/6 Bath

Chatham, Massachusetts, United States

https://wavefront-media-co.aryeo.com/sites/78-moonpenny-ln-chatham-ma-02633-18231472/brandedbrbrWelcome to Over The Moon located in the heart of Chatham's Gold Coast just off Stage Harbor.brbrWhen it comes to location, your search ends here.brbrNewly renovated for 2025. What makes this home the ultimate luxury experience A 2000+ SF patio/pool/outdoor kitchen/fire pit/dining area/lounge area and more. From this convenient address you can take your kayak out for a trip up the Oyster Pond River, you can paddle board out to Stage Harbor and you can bike into quaint Chatham center. The home has deeded beach rights to Stage Harbor. Walkers will find the thirty-minute stroll to town scenic and easy; the majority of the trip has sidewalks. We are just off ''The Loop'' which is a 3-mile walking/running loop in Chatham.brbrThe estate is located on quiet dead-end street tucked off of Stage Neck Road. The kitchen features a chef's six-burner gas stove, a nine-foot island and every accessory one could ask for. Wrapping around the opposite side of the kitchen is the dining area with seating for six to eight people. This large room opens to a living space with sitting area featuring a wood burning fireplace and television. Directly off the opposite side of the kitchen is additional den with more areas to lounge and double French doors leading to the front patio with a large sectional couch..brbrThere are three master suites. The first bedroom is located off the main living room and features a king-sized bed, half vaulted ceilings, and private master suite bath. There is also a private sitting area in the back yard located just off the hallway to the master suite. The newest addition to the home has first-floor master suite with a king bed & twin trundle bed in a bonus room. Upstairs is a large master suite with a couch & Juliet Deck overlooking the back yard. A large bath with a skylight shower gives you the feel of a sun-drenched outdoor shower. There is also a large walk-in closet that can be used as a home office if you need to have a working vacation.brbrThere are two bedrooms & a full bath located on the second floor of the main section of the home. You will find a center bath, a bedroom to your right with a queen bed and kids room to your left with 3 twin beds.brbrThere is a finished basement with a sectional couch, TV, bar area, ice maker, half bath and laundry. A great space for the kids to play.brbrOn the grounds of the home you will find a large and expansive yard and pool area. Of course, no cape house is complete without an outdoor shower!brbrWe do have some toys, beach items and other necessities of summer, so please inquire about anything specific.brbrWelcome to Chatham!

Bed

Bath

Sleeps

$1743.08

/ Nightly

Private Vacation Home

Private Beach, Water Views, Incredible Location!

Chatham, Massachusetts, United States

Summary:brbr16695 - Tide's Edge: Private Beach, Water Views, Incredible Location!brbrbrbrThe Space:brbrWelcome to Tide's Edge, a serene oasis on the shores of Chatham Harbor. This three-bedroom, three-bathroom retreat is perfectly designed for families seeking a quintessential Cape Cod escape. Wake up to the gentle lull of waves and the smell of salty sea air. Just 50 yards from your doorstep is a private beach. Inside, the home is a blend of comfort and coastal elegance, featuring newly renovated interiors with a charming nautical theme. brbrThe spacious living room, with its smart TV and central air, offers an inviting space to relax on rainy days. Each bedroom boasts king-size beds, window unit ACs, and ensuite bathrooms, ensuring privacy and comfort. Step outside to discover a large deck with sweeping 180-degree views of the harbor, ideal for morning coffees or evening cocktails. Gather around the wood fire pit as the sun sets, or rinse off the day in the outdoor shower. brbrJust a short stroll from the Monomoy National Wildlife Refuge and a quick drive to bustling downtown Chatham, your days can be filled with exploring trails or savoring local flavors. The Impudent Oyster and Chatham Squire serve delectable meals and great drinks - two local favorites! Whether you're lounging on the deck, exploring Chatham, or simply basking in the natural beauty, Tide's Edge offers the perfect backdrop for lasting memories. Book your stay today and let the waves of Chatham rejuvenate your spirit.brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 8brBedroomsbr-Total 3br-1st Floor Bedroom: 1 Queen Bed, 1st floor (w/ Ensuite Bath)br-2nd Floor Bedroom: 1 King Bed (w/ Ensuite Bath)br-2nd Floor Bedroom: 1 King Bed and 2 Twin trundle beds (w/ Ensuite Bath)brBathroomsbr-Total 3br-1st Floor: full bath with showerbr-2nd Floor: full bath with shower/tub combobr-2nd Floor: full bath with showerbrOther Amenities brCentral AC with supplemental window units on 2nd floorbr-WiFibr-Smart TVsbr-Streaming Servicebr-Washer/Dryer br-Propane grillbr-Gas Fireplacebr-Wood Fire pitbr-Outdoor Showerbr-Please note outdoor amenities are available seasonallybr-Please note there is an exterior camera on the property that records front of house/driveway br-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-Parking for 2 cars maximumbr-C0524830550brbrbrbrbrOther Things to Note:brbrThere is a security camera facing the front/driveway.

Bed

Bath

Sleeps

$512.79

/ Nightly

Private Vacation Home

Pool Table, Bar, Ping Pong, Sun Rm, Deck,4 BR, Private

Chatham, Massachusetts, United States

brThis North Chatham 4 BR home with central AC has plenty of room for families to spread out and enjoy a relaxing Chatham vacation! With 4 living areas including a sun room, a lower level with pool table, bar, ping pong, a Foosball table and a new outside deck overlooking the back yard, there's plenty of room for everyone to either spend time together as a family or find your own space.brbrThe first floor includes a spacious living room with gas fireplace and adjoining dining area. French doors open to a beautiful 3 season sun room, the perfect place to work on a jigsaw puzzle or play a game of scrabble. Step outside to a lovely brick patio with table and chairs.brbrBack inside you'll be impressed by the fully equipped kitchen featuring high end appliances. A slider opens to our large deck with dining table, gas grill and additional sitting area. Back inside, the hallway leads to 3 bedrooms; 2 queens and a twin, and a full bath with tub and shower.brbrThe lower level offers a spacious area where kids and adults alike will find plenty of entertainment options. The main attraction is the pool table, but there's much more than that. A wet bar and large flat screen TV provides yet another area to relax with friends and family. Maybe a game of Yahtzee at the bar after a day at the beach brbrThis large room also features a gas stove for cool autumn nights as well as a futon which can sleep two. Sliding glass doors offer access to the beautifully landscaped grounds, an additional small patio and an outdoor shower.brbrA separate game room includes a ping pong table and Foosball table. Down the hall is another full bathroom, large Maytag washer and dryer, and a 4th bedroom with a queen size bed.brbrEnjoy the beauty and peacefulness of nearby Stillwater Pond, which is another amenity of this property. Beautiful Pleasant Bay beach is only one mile away. Other beaches, both salt water and fresh water, are very nearby as well! Bring your bikes or rent them locally because the well-maintained bike trails are also close by too.brbrDowntown shopping and restaurants, Chatham Angler baseball games and Friday night band concerts are a short 2.4 miles away. There are several nature trails around town including the Training Field Triangle Conservation Area which can be found nearly across the street. The town as well as our local chamber of commerce maintain excellent websites with lots of helpful information for visitors and we’re always happy to help answer questions or make recommendations too…. Please don’t hesitate to reach out to us for other information or questions! . And we play pickleball if you’re looking for a game!!

Bed

Bath

Sleeps

$1064.39

/ Nightly

Private Vacation Home

22 Veterans’ Field Rd., Chatham, MA: Home Plate

Chatham, Massachusetts, United States

Description:br*Four bedrooms (plus outbuilding with daybeds sleeping four and heating/cooling…great for teens!)br*Beds for twelve (max of 12 occupants)br*2 ½ baths; enclosed outdoor showerbrbrHouse Description: This is a hidden gem just a short walk to Main Street in Chatham! The main house has three zones of central air and has been beautifully renovated. The first floor suite has full bathroom with heated floor and extra deep tub as well as a walk-in closet. With four bedrooms, this house is suitable for two families to share. This home features outdoor and indoor living at its best! Walk one minute to the large town playground and five minutes to Oyster Pond Beach. Drive five minutes to area beaches. Enjoy a burger at the Red Nun just around the corner, and walk three minutes to the shops and restaurants of downtown. The patio in the shape of a home plate features a propane fire pit and outdoor kitchen. Take advantage of the relaxing enclosed outdoor shower. Just past the backyard fence is the best field in the Cape Cod baseball league, the top amateur league in the country. When you are lucky enough to experience a home game, it is a truly magical family atmosphere. You will have the best view in your own backyard when sitting in the lifeguard-chair-style stadium seats (also a nice spot for morning coffee or evening cocktails)! The yard is shaded and private. As a bonus, there is a renovated outbuilding with a hang-out space, desk, Roku TV, X-box gaming system, and extra sleeping for four in twin daybeds with twin trundles, including heat and AC. Please copy and paste the link below to access information about restaurants, shopping, recreational activities, and the house. https://docs.google.com/document/d/1jzXhS7F-228TGr7RZbToCQNyV_iTl2q2Ef-aePGEj2g/edit usp=sharing

4

Bed

2

Bath

12

Sleeps

$1356.58

/ Nightly

Private Vacation Home

Sweeping Water Views, Deeded Beach Access, Pet Friendly and AC

Chatham, Massachusetts, United States

Summary:brbrExpansive 4 BD / 4 BA Property with AC, and sweeping views of Crows PondbrbrbrbrThe Space:brbrThis home is represented by Nauset Rental, a local vacation rental management company. brbrbrbrThe perfect vacation destination does exist and it offers private/deeded beach access just a short walk away! This property sits atop a knoll offering sweeping views of Crow’s Pond - an inlet of Little Pleasant Bay - and provides direct access to a private neighborhood deeded beach & dock. The location of this rental home is great for swimming, fishing, kayaking or simply just relaxing by the shore. The large, private yard offers plenty of outdoor space for the family to enjoy. An evening BBQ, eating dinner under the stars with the family or a competitive round of freeze tag... the possibilities are endless!brbrbrbrUpon entering the property you’ll find a large family room with cathedral ceilings, plenty of space for the family to gather while catching up on the day’s activities, reading, coloring or simply watching a movie. No one will feel left out as there is ample seating for everyone to gather together. The welcoming family room leads directly into the large open kitchen/dining room with floor to ceiling windows & sliding glass doors. Dinner preperation is easy-breezy in the updated kitchenwith a large butcher block island and the dining ining room table with seating for 10 invites the entire family to dine together & make memories.brbrbrbrThe main hall of the 1st floor leads you to a small half bathroom & three of the four bedrooms that the home provides. Bedroom #1 boasts a king size bed & a full bathroom with shower stall. Bedroom #2 offers a comfy queen size bed and Bedroom #3 offers 4 twin size beds with ensuite bathroom (tub/bathtub combo). This room is PERFECT for the kiddos in your group. Lastly, head up the stairs to find Bedroom #4 offering a queen size bed. There is a full bathroom on the second floor offering a separate shower & bathtub.brbrbrbrThe memories made at Chatham Seascape will become your fondest memories of Cape Cod.brbrbrbr**We welcome approved low-impact DOGS - TENANT must reach out to Nauset Rental with dog details for approval either before making reservation or within 48 hours of submitting online reservation** We will need to know the following information:brbrbrbr*Any shedding brbr*Any issues with accidents - urination or throwing up brbr*Any issues with chewing furnishings brbr*Barking while unattended or while attended brbr*Does your dog receive flea and tick preventative brbr*Are you confident you can leave property with no sign of your dog when you check out brbrbrbrLayout of Bedrooms & Bathrooms:brbrMain Level:brbrBedroom #1 - King size bed brbrBedroom #2 - Queen size bed brbrBedroom #3 - 4 Twin size beds brbrHalf bathroom brbrFull bathroom with stand up shower stallbrbrFull bathroom with tub/shower combobrbrbrbrUpper Level:brbrBedroom #4 - Queen size bed brbrFull bathroom with seperate tub and showerbrbrbrbr**Typically renters bring their own sheets, towels etc. Please inquire if you are interested in having linens delivered to the home for an additional fee.**brbrbrbrOther Things to Note:brbr-

Bed

Bath

Sleeps

$384.22

/ Nightly

Private Vacation Home

Great Location in Chatham Walk to town shop, dine, band concert, cape baseball

Chatham, Massachusetts, United States

Have a wonderful time on your Cape Cod vacation! Our home includes a new deck for your summer cookouts an outdoor shower, three bedrooms, bathroom, living room, kitchen,dining area and a cozy family room on the lower level. It also has central air conditioning as well as a washer and dryer. We provide wireless internet and cable TV. beach chairs, boogie boards sand buckets, shovels and minnow nets for your convenience. It is centrally located in the town of Chatham and just minutes away from Hardings Beach, Schoolhouse Pond, Oyster Pond, bike trail and walking distance to the many shops on Main Street. Explore all the fun things Chatham has to offer like beaches, restaurants, shopping, concerts in the park and Cape Cod baseball. Short walk from our home will get you there ! The bike path is up the street. Saturday to Saturday only bookings

Bed

Bath

Sleeps

$599.43

/ Nightly

Private Vacation Home

Gorgeous Home with Game Room Dog Welcome!

Chatham, Massachusetts, United States

Summary:brbr16675 - Summer Stunner: Gorgeous Home with Game Room Dog Welcome!brbrbrbrThe Space:brbrAnother Cape Cod vacation means a trip to captivating Chatham, where people flock from around the world to experience this amazing vacation destination. Your next vacation home base can include amazing outdoor spaces, a game room and more: this home is truly a Summer Stunner!brbrPulling up to the home, the peace and quiet of the neighborhood welcomes you in, with trees and a lovely yard surrounding the home. Indoors, step into a beautiful foyer, where you can kick off your sandals after a day at the beach. Further into the home, a spacious living room with wall mounted TV and views of the backyard through the large bay window awaits, with the adjacent sitting area all bathed in natural light.brbrDownstairs, an awesome game space and TV room invite you down for a fun evening of competition at the ping pong table and dart board, and movie watching on the comfortable sectional in front of the large TV. brbrThe sleeping quarters of the home are located just past the living room, where three stylish bedrooms that comfortably sleep 8. The primary bedroom includes a private en suite bathroom. brbrOutdoors, an incredible entertainment space is ready for your summer sun and starry nights, with a fire pit, outdoor lounging, and outdoor dining table all on a spacious deck, surrounded by greenery for your four-legged friend to run about. brbrOther amenities include a washer and dryer, central A/C, and a spacious outdoor shower. The wonders of Chatham are ready for your next vacation, with a quintessential New England downtown full of shops and restaurants, immaculate beaches and more. Make your next vacation one to remember at the Summer Stunner. brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 8br-2 Floors (Ground Floor + 1st Floor)br-1,644 Sq Ftbr-3 Bedroomsbr-Bedroom #1: 1 King Bed with En Suite Full Bathroom, 1st Floorbr-Bedroom #2: 1 King Bed, 1st Floorbr-Bedroom #3: 2 Queen Beds, 1st Floorbr-2 Bathroomsbr-Bathroom #1: En Suite Full Bath with Shower, 1st Floorbr-Bathroom #2: Full Bath with Tub/Shower Combo, 1st Floorbr-Fully Equipped Kitchen with Dishwasherbr-Central A/Cbr-Indoor Fireplace is NOT for guest usebr-Smart Lock/Self Check-Inbr-WiFibr-TV with Cablebr-Washer & Dryer (1st Floor)br-Game Room with Ping Pong Tablebr-Deck with Outdoor Dining and Loungingbr-Propane Grillbr-Outdoor Showerbr-Private Yardbr-Fire Pitbr-5 Minute Drive to Jackknife Beachbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0405730550brbrbrbrThe Neighborhood:brbrGeneral

Bed

Bath

Sleeps

$450.65

/ Nightly

Private Vacation Home

Charming Walk to Beach Chatham-Bayview Cottage 3 BR--Central A/C; Wi-Fi

Chatham, Massachusetts, United States

Every room in this year-round home has been totally renovated and redesigned just a few years ago. The Living Room has been renovated in Winter 2025. See the photos. Bayview Cottage features central air conditioning throughout, gleaming hardwood floors in living areas, a tiled kitchen floor with gas stove, stainless appliances w/ dishwasher and microwave, granite counters, breakfast bar, and separate prep area/wine bar with wine cooler. Enjoy the comforts of this tastefully decorated ranch 4/10 mile stroll from Forest Beach, conservation area and near a neighborhood tennis court. On the calendar you will note that during the high Summer Season (June to August, we do a minimum of 7 day/weekly rental.brThere is also an outdoor shower for after your beach trips. It is a short distance to the inlet to Taylor's pond where there is a landing for fishing, kayaking, or paddle boarding.The village center is just 3 miles for unique shopping, fine dining, large playground, weekly band concerts, the Coast Guard Lighthouse, and the nationally renowned Chatham Anglers NCAA baseball games where MLB scouts search for new talent.br brbrKeywords: Home has central air, new kitchen and baths, new wood flooring, tile, furniture, and all rooms are tastefully decorated. Short walk to Forest Beach or Pleasant Street beach.

3

Bed

2

Bath

6

Sleeps

$1434.49

/ Nightly

Private Vacation Home

Charming home in downtown Chatham

Chatham, Massachusetts, United States

Main Street in Chatham! Spend your summer vacation relaxing on the front porch of this charming, quintessential Cape Cod home in downtown Chatham. This highly sought after Main Street location makes for an easy walk to both Lighthouse Beach, and the village, where all of the local shops are found. Offering 5 bedrooms that can sleep 10 guests in 1 king, 2 queen, 1 double and 2 twin beds; this large home is perfect for the extended family holiday. Large front and back yards, granite kitchen island, and tons of space. Rinse off the salt and sand in the enclosed outdoor shower after a day in the waves and sun, then grill up some dinner in the backyard while you relax with a cold beverage. Then head into town for a movie and ice cream and don't forget those band concerts on Friday nights. Central a/c for your comfort on those hot summer nights, and a large flat screen TV for your entertainment. Wonderful home to make your Cape Cod vacation memories in! Call us at Chatham Rentals and let us help you plan your stay.

Bed

Bath

Sleeps

$545.92

/ Nightly

Private Vacation Home

Location is Everything! Walk to 3 of North Chatham's Most Scenic Salt Water Beaches

Chatham, Massachusetts, United States

Location is everything! Walk to 3 of North Chatham's most scenic salt water beaches and a short trip to Chatham's coveted downtown shopping and dining scene. Welcome to 25 Spring Hill Rd a light-filled salt box Cape. This home invites all searching for their next summer get-a-way. Relax and entertain on 2 decks or unwind in the back yard with some memorable conversation around the firepit. There are three comfortable bedrooms and 2 baths in this lovingly appointed retreat. The first floor primary affords a spacious setup with a king bed. On the second floor separated by a catwalk loft and guest bath are 2 additional large bedrooms, one queen and one king. There is a vaulted great room that connects to a recently updated kitchen. The high ceilings and skylights throughout make for bright enjoyable spaces brOwner also provides a portable crib, high chair, and baby bath tub!

Bed

Bath

Sleeps

$1553.25

/ Nightly

Private Vacation Home

Gracious home 200 yards to private beach

Chatham, Massachusetts, United States

This beautiful Cape Cod gem was built as a barn in the 1800s and converted to a home by our grandparent's in the 1950s. It has newly updated kitchen, bathrooms and central air conditioning.brbrThe first floor includes one bedroom with a double bed, one bedroom with a king bed, two full baths, a living room area with a fireplace and flatscreen TV, a large kitchen with a dining area, and access to an outdoor deck.brbrOn the second floor, you'll find one bedroom with a twin bed; one bedroom with a queen bed; and a “great” room with four twin beds, a TV, and a separate laundry area.brOutside, there’s a large mahogany deck with many chairs, lounges, and tables—perfect for enjoying views of the expansive front yard and backyard.brbrAccess to a private beach is just 200 yards away and includes a boathouse and beach equipment. This beach is located 1.5 miles from the saltwater Oyster Pond and Lighthouse Beach and 2 miles from downtown Chatham. No commercial activities can be found within 1.5 miles of this property, so our home has been enjoyed by those seeking a peaceful, serene, and relaxing atmosphere.brbrWe ask all visitors to our property to be respectful of the home and its furnishings and to take care of it during their visit! If you feel your group may be hard on the home, this home will not be a good fit. This is a Saturday-Saturday rental only.

Bed

Bath

Sleeps

$439.06

/ Nightly

Apartment

Perfect couples escape. Close to beaches, great biking & walking & pet friendly.

Chatham, Massachusetts, United States

This open studio apartment is the perfect stay. Privacy, beach proximity, pet friendly and CLEAN. Lots to do and see in Chatham and this rental has beach chairs, kayaks, private boat tours and more. With over a 1000 sq ft of open living space, nautically decorated you won't want to leave the comforts. Complete with two queen beds, desk, kitchenette, full bath, large closet, internet, cable, A/C and more, this large inviting space is perfect for a get way on the cape. The unit has a small refrigerator in it and a full fridge on the first floor for extra needs. Guests have access to fire pit and grill to take to the beach. Come visit and make this a memorable vacation.

Bed

Bath

Sleeps

$260.79

/ Nightly

Private Vacation Home

South Chatham cottage walk to beaches, dining, tennis, shops, bike path.

Chatham, Massachusetts, United States

This cottage is an affordable Chatham getaway destination for a couple or small family who want to experience Cape Cod. Located south of Route 28 and close to all that South Chatham has to offer. Within walking distance of beaches (0.7 miles to Forest Street beach and overlook with walking trails), free public tennis (Judy's Lane), restaurants (Drifters, Pisces), shops, roof top boat launch (Mill Creek), and the bike path. brbrAmenities include washer/dryer, WiFi, flat screen smart TV , gas grill, outdoor shower, and firepit. brbrShort drive into Chatham Center or Harwich Port for many more activities - more saltwater beaches, lakes and ponds with swimming and boating, clamming, fishing, fine dining, seal watches, the Fish Pier, Lighthouse, public boat launch, and much more. Cape Cod National Seashore and Hyannis airport/ferry/museum are well within a 1 hour drive. brbrSaturday to Saturday weekly rentals from late June to late September. brbrImportant things to know:brbr1. Tenants must supply their own linens. br br2. There is no A/C, but there are fans for those days with no cooling sea breeze. brbr3. Sorry, no pets allowed out of consideration to future guests, and our own family members who are breathing challenged by pet hair.brbrExtensive large improvement projects and smaller updates were completed over the 21/22 off-season: new windows and window treatments, new floors, interior doors, new front yard walkaway, new driveway, and new backyard patio were the projects. A Keurig coffee machine, BOSE sound system, new Weber gas grill, and outdoor patio lighting were added as new amenities. brbrOff season (October to May) rentals would be considered, please inquire for details.

Bed

Bath

Sleeps

$1083.45

/ Nightly

Private Vacation Home

Four Bedroom - Short Distance to Downtown Chatham -- 2/10's mile to Oyster Pond Beach Area

Chatham, Massachusetts, United States

One block to Downtown Chatham and 1/2 mile to Oyster Pond, a Nice Saltwater Inlet with Sandy Beach, and Bathhousebrbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbrEnjoy this immaculate 4 bedroom, 3 1/2 bath summer home featuring bright colors and hardwood floors throughout. Central Air Conditioning has been added to the property. You'll find a spacious eat in kitchen, two living space areas both with cable televisions. Relax on the rear porch or front deck, perfect for outdoor dining or reading a book. The backyard is adjacent to Chase Park; the home is located very close to activities in Town-- Chatham Band Concerts, Chatham Angler's ballgames, restaurants, shopping, coffee, ice cream, galleries, playground and so much more!brbrThere is one bedroom on the first floor with a Queen bed. On the second floor there is a second bedroom with a Queen bed, third bedroom with two Twin beds side by side and the fourth bedroom with king bed and private bath. There is a second full bath on the second floor. Off of the living room and kitchen on the first floor there is another full bath.brbrFirst Floor: Bedroom #1 - QueenbrSecond floor: Bedroom #2 - Queenbr Bedroom #3 - Two Twins side by sidebr Bedroom #4 - King (two twins put together)br br* Additional fees:br- $220 non-refundable reservation fee br-Damage Protection Fee - $30br-Guest Services Fee - 3.5%br- Cleaning Fee - $350br- All applicable taxesbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO SMOKINGbr* NO PETS ALLOWEDbr* OCCUPANCY: 7 (Adults and children)br* PARKING FOR 4 VEHICLESbr* SHEETS AND TOWELS ARE NOT PROVIDED. WE CAN PROVIDE INFORMATION FOR LINEN RENTALS.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.

Bed

Bath

Sleeps

$1234.49

/ Nightly

Private Vacation Home

Water View-Walk town/beach, pets considered, Linen Option

Chatham, Massachusetts, United States

It's all about LOCATION-just steps from deeded access to the Mill Pond where you can launch your Kayak without ever having to put it on your car. This spacious and well appointed home is just off of the LOOP in a sought after private neighborhood. The Marina and Yacht Clubs are a short distance away with Main Street and Oyster Pond nearby also. The interior has recently undergone an updating with all walls and ceilings painted throughout.brbrThis house is not a traditional rental, it is a home where memories are made. Over the years it has been the venue for special wedding anniversary years.e.g. 25th, 40th, 50th and for one couple and their family 60th. as well as for those milestone birthdays up to and including the 90th. Many families of the bride or groom have stayed here for the last minute wedding preparations (including my own two daughters). brbr Read the reviews--extended families love it, perfect for that entire family gathering. Check out the floor plans-you will be very comfortable here. I should know I just spent a recent weekend there with my children and grandchildren--8 adults and 8 children Everyone was quite comfortable.brbr The minute you pass through the entry door you will find the fully equipped well appointed Chef's kitchen with its cherry cabinets, Bosch and Electrolux stainless steel appliances, and wet bar. The center island is great for hosting a buffet meal or for just standing around enjoying snacks and drinks with guests. brFrom the kitchen, you will step down into the 400 plus square foot sun room with its brick floor, gas log fireplace, comfortable wrought iron furniture, a large flat screen TV . In addition there is a farm table for dining or game playing. All of the above make this room is a magnet for gathering. Overlooking the patio and backyard is an added bonus.brbr You can step out through the sliders to the brick patio with a comfortable brick and bluestone wall for seating, recliners, and tables and chairs for Al fresco dining.brSipping your morning coffee, checking emails or just enjoying nature adds to the serenity and ambience. brbrFrom the sunroom, you can also step up into the formal dining room for eating or for card playing or puzzles. brbrFrom the dining room you enter one of the four large common rooms. This first one has a gas log fireplace, large bay window with window seat and plenty of room for many to gather and share memories or for one or two people to sneak away and enjoy some quiet time-meditate, read and relax.brbrWhile heading for the first floor bedrooms and baths you will pass the second common room which is a cozy den with a queen sleep sofa and pocket doors. There is also a flat screen TV and plenty of books to read. Should the need arise for a quasi 6th bedroom the pocket doors can be closed for privacy.brbrThere are four more rooms on the first floor. brbrThe first floor Primary suite has its own bath, a queen bed (with a brand new queen mattress), twin trundle beds and a flat screen TV. It is adjacent to a very large study(400+ square feet and the third common room) with a gas fireplace and very comfortable leather furniture, and another flat screen TV. There is also a desk and printer for those who have to work while vacationing. The study overlooks the second patio and the gardens at the rear of the home. This can serve as a family suite when combined with the Master or can be perfect for a couple wishing to have their own private space away from it all.br.brbrOf the other two bedrooms on the first floor one has two twin beds and the other has a queen and a twin. These two bedrooms share a bath off of the hallway. (NOTE BENE: Pictures haven't been updated to show bedroom with queen and twin-picture shows two twins)brbrThere are pictures of all of these rooms with the listing. All five bedrooms plus the den and sunroom have ceiling fans in addition to central air. brbrYou now ascend the bridal staircase to the second floor. At the top of the stairs to your left, you will see the Great Room (the fourth common room) with its wet bar (with refrigerator), views of the water and stairs leading up to the roof deck. The Great Room has numerous 6 foot long windows overlooking the back yard and gardens. There are also sliders off to a small balcony-great. place for meditating. This room also contains a large flat screen smart TV for streaming, There are two tables for game playing, puzzles or dining. Perfect place for mixing up those end of day martinis prior to dinner.brbrbr To the right of the bridal staircase you will see the magnificent second floor Primary Bedroom with a brand new King size bed and mattress, private sitting area (that has a full-size sleep sofa) and a TV. This room has its very own special black granite and white marble bathroom. This bathroom has a cast iron soaking tub and a rainforest shower. brThis room is perfect for the bride to be and her attendants prior to the wedding. (many brides to be have stayed here, including my own two daughters.) The drapes are room darkening for those wishing to sleep in. NOTE BENE: PICTURES HAVEN'T BEEN UPDATED TO SHOW THE NEW KING BED)brbrThe second bedroom on this level has a queen size and a twin size bed. There is also ample closet space and a beautiful view of the outside. The drapes are room darkening for those wishing to sleep in.brbrThere is a fourth bath in the hallway that services the bedroom as well as general guests.brbrThe easily accessible 475 square fort roof deck has reclining chairs for sunning and three tables that seat twelve. From here there are water views-sometimes as far as the Atlantic. There are also views of the Mill Pond, Mitchell River, the drawbridge and parts of Stage Harbor.brbrThe outside lot is professionally landscaped with a lush green lawn and a wide long expanse at the rear of the house for lawn games or just relaxing.brbrThe closest Beach, Oyster Pond, is just a 10-minute walk away and downtown is a 15-minute walk. There you will find many great restaurants and shops as well as a movie theater.brVeterans Field, the home of the Chatham Anglers, is less than a mile away. The entrance to the Cape Cod Rail Trail for biking off of Crowell Road is about a mile away.brbrBe sure to check out the accompanying floor plans to see how this property can best serve your needs as well as the video which appears after the second picture.brbrThis location is ideal--convenient yet quiet. Chatham is midway between the Sagamore Bridge and Provincetown. There is a Linen Option for an additional fee or you may bring your own or rent on your own from one of the linen rental companies which will deliver to the house and retrieve them on your departure.brAt the discretion of the owner a security deposit may be required.brFor immediate response, you can email me at chathamrental9gmail.com. Or dial seven eight one, four three nine, nine zero eight five.brbrCheck the reviews--renters LOVE this house and location.

Bed

Bath

Sleeps

$992.43

/ Nightly

Private Vacation Home

Water Views in Chatham!

Chatham, Massachusetts, United States

Charming, perfect location and every amenity you could want! The first floor features 2 bedrooms, one with a queen size bed and one with a pyramid bunk bed. A luxurious full bathroom with laundry area is easy to access from the bedrooms or the living room area. The kitchen is equipped with high end cabinets, appliances and fixtures to make even preparing your morning cup of coffee an enjoyable experience. There is a large living room and dining area with plenty of room to relax after a day at the beach. Step out of the living room through the French doors to access a wonderful outdoor deck and spacious back yard with water views! One of the wonderful features of this home is the abundance of natural light streaming in from the large windows, French doors and many skylights throughout the home. The second floor features a master suite complete with a queen size bed, sitting area and bathroom, perfect if you are traveling with extended family. Enjoy your stay even more because you are just steps to Pleasant Street Beach! brbrNon-refundable $500 Administrative fee, $444 Cleaning fee (Linens included), plus applicable state and local taxes. Shorter stays of 3 or more nights available off season, inquire for pricing.

Bed

Bath

Sleeps

$330.01

/ Nightly

Private Vacation Home

Movie Theater Room, Direct Access to Bike Trail!

Chatham, Massachusetts, United States

Summary:brbr16681 - Summer On: Movie Theater Room, Direct Access to Bike Trail!brbrbrbrThe Space:brbrEscape to this charming Chatham colonial with your beloved four-legged family members, offering direct access to the picturesque Cape Cod Rail Trail. This newly re-furnished vacation retreat exudes thoughtful Cape Cod style. Step out of your back door onto the Rail Trail (path in the backyard), whether it's for a leisurely bike ride or a tranquil walk with your dog, surrounded by the beauty of nature. Forest Beach on Nantucket Sound is a mere mile away, promising endless seaside delights.brbrThe ground floor of this gem features a cozy media room, perfect for evenings spent in. Upstairs, the main living space boasts an open concept design, with a spacious kitchen, dining area, and an additional living room, providing ample space for the entire family to unwind and connect. Whether you seek outdoor adventures or relaxation, this getaway offers it all. Find solace on the deck, gather around the fire pit in a private wooded setting, or dine al fresco at the picnic table.brbrA bright sun-room, with a vaulted ceiling and expansive windows, immerses you in the natural surroundings. A slider door leads to the gas grill and deck, perfect for enjoying BBQ feasts. This Chatham vacation home features spacious bedrooms, all newly furnished, ensuring your comfort. brbrIn this Cape retreat, your vacation dreams come to life, offering a balance of activity and relaxation in a tranquil setting. Book your stay today and create lasting memories in this coastal haven.brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 7br-3 Floorsbr-Ground Floor Media RoombrBedroomsbr-Total 3br-1st Floor: 1 Queenbr-2nd Floor: 3 Twins (1 Bunk + 1 Single)br-2nd Floor: 1 King Bed brBathroomsbr-Total 2br-1st Floor: Showerbr-2nd Floor: Tub/Shower CombobrOther Amenities br-Split System ACbr-WiFibr-Cablebr-Washer/Dryer on Ground Floorbr-Propane Grill br-Fire Pitbr-EV Charger located in Garage. Access through interior basement door, garage opener on wall br-Please note outdoor amenities are available seasonallybr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0291890550

3

Bed

2

Bath

7

Sleeps

Vacation Rentals By Owner In Chatham, MA

$558.45

$1688.25

$452.36

$1793.05

$1743.08

$512.79

$1064.39

$1356.58

$384.22

$599.43

$450.65

$1434.49

$545.92

$1553.25

$439.06

$260.79

$1083.45

$1234.49

$992.43

$330.01

Rent a place that suits your needs

Most popular vacation rentals in Chatham

$3031.56

$4415.39

$4501.70

$667.62

$652.36

$658.09

$660.53

$666.78

$667.29

$670.35

Most Popular Cities in Massachusetts