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From $884 per night (USD)
VRBO
Azure Cottage: Central A/C & Hot Tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedrooms- 3 Bathrooms- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $884 per night (USD)
VRBO
From $1106 per night (USD)
VRBO
Family friendly luxury home with heated pool and spa
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Gorgeous home in Chatham with a brand new heated saltwater pool and hot tub. The open floor plan, combined living and ...
From $1106 per night (USD)
VRBO
From $299 per night (USD)
VRBO
Cozy one bedroom on White pond (Must bring your own linens)
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
2 Person only. Charming little classic Cape cottage located close to town, beaches and bike trail. The cottage is nestl ...
From $299 per night (USD)
VRBO
From $2068 per night (USD)
VRBO
Location! Pool & Spa! 2 Primary Suites, Walk to Town, Beach, Chatham Bars Inn
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
**As is customary with Cape rentals, there is a cleaning fee and a 14.45% local and state lodging tax. Please enter desi ...
From $2068 per night (USD)
VRBO
From $416 per night (USD)
VRBO
Peaceful, Charming, Quiet, Airy, Cozy - Take A Look!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This 3 bedroom 2 bathroom two-story cape is private, quiet, and overlooks a lovely cranberry bog. Inside it's airy and o ...
From $416 per night (USD)
VRBO
From $899 per night (USD)
VRBO
Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
A charming 3 bedroom, 2.5 bath cape with large kitchen and private backyard, patio and deck that abuts conservation lan ...
From $899 per night (USD)
VRBO
From $1116 per night (USD)
VRBO
Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This picture perfect Townhome is set on 17.5 acres on beautiful Oyster. Beautifully and meticulously designed, this Town ...
From $1116 per night (USD)
VRBO
From $1478 per night (USD)
VRBO
Perfect House to Enjoy Family & Friends!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Main house has 3 bedrooms 2 baths. Open floor plan is great for a big group. Apartment has a full kitchen, living area a ...
From $1478 per night (USD)
VRBO
From $4300 per night (USD)
VRBO
Ocean views, path to beach, short walk to lighthouse and town, sleeps 12
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
This listing combines a large house having a deck with a beautiful view of the ocean and an adjacent cottage allowing fo ...
From $4300 per night (USD)
VRBO
From $369 per night (USD)
Expedia
Waterfront Chatham Retreat w/ WiFi & Privacy
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
1 Bedroom- 1 Bath- Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of ...
From $369 per night (USD)
Expedia
From $912 per night (USD)
VRBO
Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
1.2 acres of beautiful waterfront property. Pond is great for canoes, fishing, and swimming. Canoe provided for tenant u ...
From $912 per night (USD)
VRBO
From $2043 per night (USD)
VRBO
Chatham's Best Location / Oceanside / Walk to Town and Beaches
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
This exquisitely furnished, charming Cape Cod house is within an easy walk of Chatham's beaches, Fish Pier, Lighthouse, ...
From $2043 per night (USD)
VRBO
From $944 per night (USD)
VRBO
AC, Pool, Hot Tub, Fenced Yard, Beach vacation home
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Spacious four bedroom, two bathroom, single family home with central air, above ground pool, hot tub, fire pit, and fenc ...
From $944 per night (USD)
VRBO
From $523 per night (USD)
VRBO
Summer Hydrangea: Chatham's Truly Exceptional Summer Retreat
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Summer Hydrangea, quite possibly the finest property value for an exceptional summer rental in Chatham. Priva ...
From $523 per night (USD)
VRBO
From $412 per night (USD)
VRBO
Pondfront cottage on Stillwater Pond
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Set your clocks back 50 years, and fish for your breakfast from your own dock or row-boat. This setting has been descri ...
From $412 per night (USD)
VRBO
From $695 per night (USD)
Expedia
Walk to Private Beach Hot Tub AC Water Views The Sea Mist
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 Bedroom - 2 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $695 per night (USD)
Expedia
From $487 per night (USD)
VRBO
South Chatham, Ma. 02659. Seasonal Cottage, Walk to Pleasant Street Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Cottage has been in family for over 40 years but updated over the years. Seasonal beach cottage 1 full bath, king bedro ...
From $487 per night (USD)
VRBO
From $520 per night (USD)
VRBO
Sea views steps to Ridgevale Beach - Airy Cottage. Modern Amenities. Pet.linen
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Pet ok with approval first. Bright and airy cottage sleeps max 5 (2 BR - 1Q, 2T) plus single pull out sofa bed in hi liv ...
From $520 per night (USD)
VRBO
From $382 per night (USD)
VRBO
Walk to Ridgevale Beach in 7 minutes, Central Air, Beautiful yard Fast Internet
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Adorable Chatham Ridgevale Beach House With Beautiful Gardens! *******7 night minimum stay Saturday to Saturday***** ...
From $382 per night (USD)
VRBO
From $944 per night (USD)
VRBO
Charming Waterfront House in Chatham
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
Very private lakefront setting with spectacular views and private beach. Filled with Charm. It was the original Ice Hous ...
From $944 per night (USD)
VRBO
From $562 per night (USD)
VRBO
Walk to Beach Central AC WiFi Beach Pearl
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
2 bedrooms- 2 baths- sleeps 5 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many o ...
From $562 per night (USD)
VRBO
From $653 per night (USD)
Expedia
Sea Glass Cottage Near Nantucket Sound Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
3 bedroom- 2 bath- sleeps 7 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of ...
From $653 per night (USD)
Expedia
From $350 per night (USD)
VRBO
Spacious, private cottage just a few minutes walk to Ridgevale Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summer living less than a 1/2 mile from one of Cape Cod's best beaches! This home offers room to spread out, with living ...
From $350 per night (USD)
VRBO
From $353 per night (USD)
VRBO
Secluded Chatham Cottage Near Hardings Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to our renovated 'old Cape' style cottage, with a sunny, open floor plan, brand new appliances and furnishings, ...
From $353 per night (USD)
VRBO
From $694 per night (USD)
VRBO
Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in the heart of Chatham, Cape Cod, Massachus ...
From $694 per night (USD)
VRBO
From $1268 per night (USD)
VRBO
LOCATION, LOCATION 200 YDS TO CHATHAM VILLAGE & BEACH WITH GREAT WATER VIEWS
Bedrooms:
3
Bathrooms:
5
Sleeps:
13
Location ! Location! Location ! Everything within walking distance . . . 200 yards to Chatham downtown, 200 yards to pub ...
From $1268 per night (USD)
VRBO
From $368 per night (USD)
VRBO
Quiet North Chatham Getaway with Scenic Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
1 Bedroom- 1 Bathroom- Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $368 per night (USD)
VRBO
From $806 per night (USD)
Expedia
Lake front, Near Beach, AC, WiFi, Pet Friendly near Bike Path
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedroom - 2.5 Baths - Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $806 per night (USD)
Expedia
From $517 per night (USD)
VRBO
Chatham Ranch Retreat Near Hardings Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 Bedroom - 2 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $517 per night (USD)
VRBO
From $737 per night (USD)
Expedia
Walk to Beach, AC, WiFi, Private, Fire pit, Dogs Welcome
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
4 Bedroom- 3 Bathroom- Sleeps 9 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $737 per night (USD)
Expedia
Click For Pricing
VRBO
Close to Beach and Town Pet Friendly A C The Cape House
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedrooms- 2 Bathrooms- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
Click For Pricing
VRBO
From $612 per night (USD)
Expedia
Beachside Bliss: Dog Friendly & Breezy Stay
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
3 Bedroom - 2.5 Baths - Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $612 per night (USD)
Expedia
From $736 per night (USD)
VRBO
Ocean views Walk to Beach Pet Friendly AC Private
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
4 Bedroom - 4 Baths - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. This ...
From $736 per night (USD)
VRBO
Click For Pricing
Expedia
Captain's Row: Pool, Tennis & Chatham Charm
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
2 Bedroom - 3 Bathroom - Accommodates 6 Comfortably During peak summer weeks it is typical for our properties to require ...
Click For Pricing
Expedia
From $500 per night (USD)
VRBO
The Cape Escape: Walk to Harding's Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
4 Bedroom- 2 Bathroom- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $500 per night (USD)
VRBO
From $1742 per night (USD)
Expedia
Historic Sea Captain's Home in Downtown Chatham
Bedrooms:
5
Bathrooms:
8
Sleeps:
18
8 Bedrooms- 5.5 Bathrooms- Sleeps 18 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. ...
From $1742 per night (USD)
Expedia
From $1999 per night (USD)
VRBO
Walk to Beach Heated Pool Pet Friendly AC WiFi Sand Simeon
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
6 bedrooms- 6.5 Bathrooms- Sleeps 14 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. ...
From $1999 per night (USD)
VRBO
From $497 per night (USD)
VRBO
3 bed 3 bath. Premium linens provided. Pet friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
When you arrive you will find that our architect maximized light, air and views, with great flow from the upstairs vault ...
From $497 per night (USD)
VRBO
From $899 per night (USD)
VRBO
Charming , very private 4 bedroom, 3.5 Bath Cape. Walk to Town & Oyster Pond
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
A charming 4 bedroom, 3.5 bath cape with large kitchen, private backyard, includes all amenities, patio and deck that ...
From $899 per night (USD)
VRBO
From $589 per night (USD)
VRBO
Location, location, location
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Brand new remodeled kitchen. Charming 4 bedroom cape. Great location! Not your typical rental. We only rent a few we ...
From $589 per night (USD)
VRBO
From $2041 per night (USD)
VRBO
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!
Bedrooms:
10
Bathrooms:
9
Sleeps:
21
This wonderfully renovated 1877 home, nestled in downtown Chatham, is centrally located within walking distance from eve ...
From $2041 per night (USD)
VRBO
$Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.\n$
From $3047 per night (USD)
VRBO
Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.\n
Bedrooms:
5
Bathrooms:
8
Sleeps:
18
New heated gunite pool. 18X40 with automatic pool cover, and completely fenced in for safety. Design includes many plant ...
From $3047 per night (USD)
VRBO
From $384 per night (USD)
VRBO
Charming Cape Cottage in Chatham, 2 Min From Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Forest Sands cottage is comfortably decorated in Classic Cape style, a 2 minute walk from Forest Beach, and 10 minute sp ...
From $384 per night (USD)
VRBO
From $210 per night (USD)
VRBO
Delightful Cottage for Two
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This true Cape Cod cottage is ideal for a couple. Located in a 6 acre private community on beautiful White Pond. It is n ...
From $210 per night (USD)
VRBO
From $289 per night (USD)
VRBO
Stay in a Chatham Windmill! Beautiful Water View, Steps to Beach & Main Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
NEWLY RENOVATED CHATHAM WINDMILL for your special Cape Cod vacation experience! Located overlooking Chatham's beautiful ...
From $289 per night (USD)
VRBO
From $325 per night (USD)
Expedia
Cute Cottage - Half Mile to Nantucket Sound! (1976)
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This cottage is perfect for a relaxing vacation. It is located in a quiet location in South Chatham, only ½ mile to Nant ...
From $325 per night (USD)
Expedia
From $399 per night (USD)
VRBO
Beautiful home near Jacknife Beach and bike trail
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
This newly renovated home has 3 bedrooms and 2 1/2 baths,and is located in a nice quiet neighborhood. This home is centr ...
From $399 per night (USD)
VRBO
From $691 per night (USD)
VRBO
Chatham Preservation Award: Antique Cape in Chatham Center
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
2010 Chatham Preservation Award Recipient This 1820 Cape was completely restored in 2008 and combines a classic exterio ...
From $691 per night (USD)
VRBO
Click For Pricing
VRBO
Harding's Beach/Oyster River Area / Walk to Water
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This summer beach house was completely renovated when purchased and the owners continue to keep up with ongoing Renos. ...
Click For Pricing
VRBO
From $658 per night (USD)
VRBO
Outermost Waterfront Chatham Home w/ Wraparound Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Right down the hill from the famous Chatham Light House, this one-floor living, 2 bedroom, 2 full bath end unit with wr ...
From $658 per night (USD)
VRBO
From $390 per night (USD)
VRBO
Charming Air Conditioned Chatham Vacation Home Walk to Beach & Tennis
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This charming house is located on a landscaped, level lot on a quiet, dead end lane just 4/10 mile from Forest Beach on ...
From $390 per night (USD)
VRBO
From $669 per night (USD)
VRBO
Charming Chatham House Walk to Downtown
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
We make it easy to plan your vacation on Cape Cod in Chatham, MA. This well-appointed, renovated home is centrally and c ...
From $669 per night (USD)
VRBO
From $286 per night (USD)
VRBO
Cozy renovated classic Cape cottage a short walk to Forest Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This cute 2 bedroom 1 bath cottage was recently completely renovated inside and is bright, clean and cozy. It is locat ...
From $286 per night (USD)
VRBO
From $2125 per night (USD)
VRBO
Exquisite Old Cape Charm, Spectacular Views, Huge Private Beach, Sleeps 20
Bedrooms:
6
Bathrooms:
13
Sleeps:
20
This is the old Cape Cod at its loveliest and most peaceful. Although the oldest part of the house was originally a cott ...
From $2125 per night (USD)
VRBO
From $256 per night (USD)
VRBO
Chatham Cottage on the Big Pond One Mile to Ocean Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Get away and relax at our cottage on White Pond in beautiful Chatham Cape Cod. The cottage has a private fresh water bea ...
From $256 per night (USD)
VRBO
From $307 per night (USD)
VRBO
Near Harding's Beach, 4 min walk to Oyster River. 3BR, 2Bath, enclosed deck area
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Just off of Barnhill Rd on the way to popular Harding's Beach, this air conditioned, updated three bedroom house off ...
From $307 per night (USD)
VRBO
From $525 per night (USD)
VRBO
Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Pet Friendly! Two bedroom luxury vacation condo on second floor of home in the heart of Chatham Village! Head up the sta ...
From $525 per night (USD)
VRBO
From $1242 per night (USD)
VRBO
SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to the SeaGlass House! Charming and bright, open concept Cape house perfect for creating long lasting memories. ...
From $1242 per night (USD)
VRBO
From $1640 per night (USD)
VRBO
Beachfront Nantucket style home with amazing views on 3 acre estate setting
Bedrooms:
1
Bathrooms:
5
Sleeps:
9
'The Bluff House' is a very private turn of the century informal home located down a private country lane directly on th ...
From $1640 per night (USD)
VRBO
Click For Pricing
Expedia
Stylish Cape in North Chatham ~ Walk to Private Neighborhood Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Beautiful cape in upscale Harbor Cove neighborhood. Recently renovated with all new furnishings and appliances. 4 BRs, 2 ...
Click For Pricing
Expedia
From $620 per night (USD)
VRBO
Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Spend your Chatham vacation at the POOL! This wonderful home is just minutes to everything downtown Chatham has to offer ...
From $620 per night (USD)
VRBO
From $375 per night (USD)
Expedia
Pet friendly home with central air (1998)
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This adorable PET FRIENDLY cape style home is located on a peaceful, residential, dead end road, close to two fresh wate ...
From $375 per night (USD)
Expedia
From $372 per night (USD)
VRBO
Charming Chatham Beach House; Walk to Hardings Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
You will love Rhododendron House -- a recently updated 2 bedroom vacation house. This private hilltop retreat is located ...
From $372 per night (USD)
VRBO
Click For Pricing
Expedia
5 Bed/2 Bath Sleeps 11. Walk to restaurants, town and more...
Bedrooms:
2
Bathrooms:
5
Sleeps:
11
Located just 1 mile from the fish pier and CBI, and 1.5 miles to downtown, we are close to all the best Chatham has to o ...
Click For Pricing
Expedia
From $343 per night (USD)
VRBO
Coastal Charm in South Chatham – Walk to Beach & Bike Trail!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Charming South Chatham Cottage - Walk to Beach & Bike Trail Escape to this peaceful South Chatham cottage, perfectly sit ...
From $343 per night (USD)
VRBO
From $952 per night (USD)
VRBO
Waterfront house on Cape Cod in Chatham, MA.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Enjoy the peaceful tranquility of our beachfront house on Cape Cod in Chatham, Massachusetts. Experience picturesque oce ...
From $952 per night (USD)
VRBO
From $815 per night (USD)
VRBO
Sea Captain's House - Beautiful Water View, Steps to Beach & Main Street
Bedrooms:
5
Bathrooms:
5
Sleeps:
9
Located overlooking Chatham's beautiful Oyster Pond, this home is the perfect location for your vacation. Take advantage ...
From $815 per night (USD)
VRBO
From $631 per night (USD)
VRBO
Sandcastle By the Beach - 300 yards to Ridgevale Beach!
Bedrooms:
0
Bathrooms:
3
Sleeps:
6
Recently renovated, beautifully appointed, adorable 3 bedroom, 1.5 bath home that is literally a 3 minute walk to Ridgev ...
From $631 per night (USD)
VRBO
From $493 per night (USD)
VRBO
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This charming and totally renovated (see updated pictures below) Chatham home is on a private road in a downtown neighbo ...
From $493 per night (USD)
VRBO
From $529 per night (USD)
VRBO
In Town Newly Renovated Cape
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Location, Location, Location – New to the rental market, this fully renovated centrally located cape home checks all the ...
From $529 per night (USD)
VRBO
From $592 per night (USD)
VRBO
STYLISH CHATHAM HOUSE
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Located within walking distance to a small beach and quick drive to the local shops and restaurants of Main Street i ...
From $592 per night (USD)
VRBO
From $874 per night (USD)
VRBO
Cozy Family Home in Chatham - Firepit, Game Room, Large Deck, Yard + More
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This lovely home is the perfect getaway for families or a group of friends looking for a home filled with entertainment ...
From $874 per night (USD)
VRBO
From $785 per night (USD)
VRBO
Stroll Chatham's Historic Downtown / Shops, Dining, Galleries, Etc.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Beautiful home located in the heart of Chatham! This lovely home offers all the amenities and decor of a modern house wh ...
From $785 per night (USD)
VRBO
From $923 per night (USD)
VRBO
THE CHATHAM TREEHOUSE 7 minutes from the Village
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to the Treehouse, just 7 mins from the village of Chatham! This beautiful, private property is nestled in the wo ...
From $923 per night (USD)
VRBO
Click For Pricing
VRBO
Downtown Chatham 4 Bedroom House
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
4 bedroom house at end of private, dead-end street in Downtown Chatham. 2 decks, views of conservation land. Listen to ...
Click For Pricing
VRBO
From $311 per night (USD)
Expedia
Bright home walking distance to Main Street with great patio, firepit & bikes
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Queen Anne Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $311 per night (USD)
Expedia
From $365 per night (USD)
VRBO
Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Renovated year round 4 bedroom house with bonus office/bunk room with central AC, walking distance to downtown Chatham. ...
From $365 per night (USD)
VRBO
From $281 per night (USD)
Expedia
Friendly retreat with a deck, AC, and board games - stellar central location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Corner Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $281 per night (USD)
Expedia
From $537 per night (USD)
VRBO
Marshside Escape: Walk to Cockle Cove
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
3 Bedroom - 3.5 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $537 per night (USD)
VRBO
From $311 per night (USD)
Expedia
Steps to Private Association Beach. End Unit Condo at Outermost Harbor.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Updated Condo at Outermost Harbor. Enjoy amazing views of the famous Chatham sandbars or catch a glimpse of playful seal ...
From $311 per night (USD)
Expedia
From $570 per night (USD)
VRBO
Stroll To Lighthouse Beach or Chatham's Charming Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
NEW LOWER PRICING! Fourth of July Week is Still AVAILABLE! Best spot in town for the Chatham Independence Day Para ...
From $570 per night (USD)
VRBO
From $699 per night (USD)
Expedia
Saltaire: Coastal Getaway Near Hardings Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 Bedroom - 2 Baths - Sleeps 6 During peak summer weeks, our properties typically require a 7-night stay, either Friday- ...
From $699 per night (USD)
Expedia
Click For Pricing
VRBO
3-bedroom house in charming Chatham with WiFi, fitness room, AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This 3-bedroom house in Chatham is perfect for your escape to relaxation. With 1 king bed, 1 queen bed, and 4 twin beds, ...
Click For Pricing
VRBO
From $466 per night (USD)
Expedia
Cozy Retreat in South Chatham (2374)
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our cozy single-family home located in beautiful South Chatham. This property features 3 comfortable bedrooms ...
From $466 per night (USD)
Expedia
From $990 per night (USD)
VRBO
Shore Daze: 096-C Luxury Living in Chatham with Pool and Hot Tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This property is professionally managed by Pretty Picky Properties Luxury Living in Chatham with Pool and Hot Tub Pool ...
From $990 per night (USD)
VRBO
From $269 per night (USD)
Expedia
New listing! Cozy, fresh and clean 1-bedroom cottage with Pond access in Chatham
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This cozy 1-bedroom cottage in Chatham is the perfect retreat for a couple’s or solo getaway. 2 occupants only please. S ...
From $269 per night (USD)
Expedia
From $513 per night (USD)
VRBO
Brand New Four Bedroom Home Near Beach and Town
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Brand new 4 bedroom, 2 bath North Chatham home near town and beach. On the first floor, the home boasts a designer kitch ...
From $513 per night (USD)
VRBO
From $1259 per night (USD)
VRBO
Private Beach, Beautiful Neighborhood, Well-Behaved Pet Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
The perfect spot, offering lovely outdoor amenities such as a large, beautiful hedged yard for outdoor activities, a cov ...
From $1259 per night (USD)
VRBO
From $1151 per night (USD)
VRBO
WATERFRONT home close to Downtown Chatham!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Soak up the sun while enjoying the lush outdoor space at our waterfront home, Queen’s Quarters. Bring or rent a kayak or ...
From $1151 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Cozy Chatham Cottage walk to Hardings beach Restaurants & downtown.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Newly remodeled 1950's era cottage with all the comforts for a great visit. Just off the living room and thru French do ...
From $402 per night (USD)
Expedia
From $423 per night (USD)
VRBO
Classic Cape House Walking Distance to the Beach - Many recent upgrades
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Recent upgrades: Complete interior painted (March 2025); Main dining table refinished (April 2025); Downstairs bathroom ...
From $423 per night (USD)
VRBO
From $892 per night (USD)
VRBO
Beautifully renovated home, outdoor space, pet considered
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Sea~a~Bella - Your perfect Chatham family vacation is here. You will find three beautiful, scenic beaches within walking ...
From $892 per night (USD)
VRBO
From $95 per night (USD)
VRBO
Chatham Retreat – 2-Month Minimum, Seasonal & Off-Season Stays RPAM117
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to the charm of Cape Cod in this fully furnished 1-bedroom, 1.5-bath condo in sought-after North Chatham. With a ...
From $95 per night (USD)
VRBO
From $1813 per night (USD)
Expedia
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Charming 5-Bedroom Home in the Heart of Downtown Chatham – Walk to Beach, Shops & More Welcome to your perfect Cape Cod ...
From $1813 per night (USD)
Expedia
From $554 per night (USD)
VRBO
500 ft to the Beach. Walk to Sand, Sun & Surf!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Looking for the perfect summer getaway? This inviting, clean Cape Cod cottage is just 500 feet from Nantucket Sound’s wa ...
From $554 per night (USD)
VRBO
From $2923 per night (USD)
Expedia
Sophisticated Chatham Oasis with Pool & Spa RPAM062
Bedrooms:
8
Bathrooms:
5
Sleeps:
12
Welcome to 84 Doane Road in Chatham, MA, where opulence meets comfort and convenience. Nestled in a prime location just ...
From $2923 per night (USD)
Expedia
From $881 per night (USD)
VRBO
Newly Remodeled Seaside Getaway with Forest Beach in your backyard!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Newly renovated home with ocean views and Forest Beach right in your backyard. Swim, lounge, kayak, hike, or play tennis ...
From $881 per night (USD)
VRBO
From $880 per night (USD)
VRBO
Luxurious Home with Pool & Game Room in Cape Cod
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
Welcome to our newly listed vacation home in Chatham, Cape Cod! This spacious 4-bedroom/4.5-bathroom house is a haven fo ...
From $880 per night (USD)
VRBO
From $751 per night (USD)
VRBO
Marsh and Nantucket Sound Views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
PETS ALLOWED WITH OWNER APPROVAL If you love the beach, views of the water and a beautiful home with every amenity, ...
From $751 per night (USD)
VRBO
Click For Pricing
Expedia
Sunny, Cape-style home with a game room, yard, firepit, & washer/dryer
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Chatham Living Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
Click For Pricing
Expedia

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Results: 317 Rentals