search location
Travel Dates:
Reset Dates
439 Rentals In Chatham
United States
Massachusetts
Barnstable Area
Chatham
Filters
Sub Areas
Goose Pond
(8)
Town Forest
(7)
Pinkwink Pond
(3)
Guests
Guests
1
2
3
4
5
6
7
8+
Price
Per Night:
Amenities
Pool
Internet
Washer
Fishing
FirePlace
Wheelchair Access
Non Smoking
Yard
TV
Balcony
Patio
Parking
AC
Microwave
No Pets
Jacuzzi
Pet Allowed
Dishwasher
Kitchen
Sauna
Crib
Smoking Allowed
Grill
On the Chatham Loop - 1 Min to the Beach!
5
2.0
8
Chatham Massachusetts Private vacation home
From $477 per night
(USD)
Quiet North Chatham 4 Bdr 2 Bath Large Lot Outdoor Shower Complete Remodel
4
2.0
7
Chatham Massachusetts Private vacation home
From $871 per night
(USD)
Chatham-Walk to Town/Beach-Multi Family Friendly
5
4.0
12
Chatham Massachusetts Private vacation home
From $729 per night
(USD)
Chatham Village - Adorable Studio Apartment in Antique Home
1
1.0
2
Chatham Massachusetts Apartment
From $260 per night
(USD)
GREAT LOCATION - Water View, Walk to beach & Town!
3
2.0
6
Chatham Massachusetts Private vacation home
From $989 per night
(USD)
Newly updated home sleeps 7, AC, free WIFI, half mile to town
3
2.0
7
Chatham Massachusetts Private vacation home
From $740 per night
(USD)
1 Mile from Downtown Chatham Walk to Pier
4
2.0
10
Chatham Massachusetts Private vacation home
From $523 per night
(USD)
Pond Front Home w/ Game Room Dog Friendly!
4
2.0
8
Chatham Massachusetts Private vacation home
From $445 per night
(USD)
Perfect for Group w/ Kids & Dogs w/ Hot Tub
4
2.0
10
Chatham Massachusetts Private vacation home
From $554 per night
(USD)
Chatham Village: Lovely 1-Bedroom Apartment in Antique Home
1
1.0
2
Chatham Massachusetts Apartment
From $268 per night
(USD)
4 Bedrooms, 2 Baths, Sleeps 8-10
4
2.0
8
Chatham Massachusetts Private vacation home
From $828 per night
(USD)
Fantastically located Chatham house - DISCOUNTED - New patio, refurbished
3
2.0
10
Chatham Massachusetts Private vacation home
From $880 per night
(USD)
Steps to Oyster Pond Private Dock!
5
3.0
8
Chatham Massachusetts Private vacation home
From $810 per night
(USD)
Historic Waterfront Home with Sweeping Chatham Water Views! Pet Friendly!
4
2.0
10
West Chatham Massachusetts Private vacation home
From $919 per night
(USD)
Tennis anyone? Beautiful, brand new construction with 8 bedrooms, 8 full baths and 2 half baths, that can sleep up to 20 guests.
8
8.0
18
Chatham Massachusetts Private vacation home
From $4973 per night
(USD)
Beautiful home overlooking Emery Pond
2
1.0
6
Chatham Massachusetts Private vacation home
From $1141 per night
(USD)
Beach Chic Chatham 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC
4
2.0
10
Chatham Massachusetts Private vacation home
From $1348 per night
(USD)
Chatham Village - Lovely 2 bedroom apartment in the antique home
2
2.0
4
Chatham Massachusetts Apartment
From $490 per night
(USD)
This lovely condo location in town, has both a brick patio and deck for you to enjoy your morning coffee on!
1
1.0
3
Chatham Massachusetts Condo
From $611 per night
(USD)
School Street in the Old Village!! Charming, new construction with attention to detail!
4
3.0
8
Chatham Massachusetts Private vacation home
Click For Pricing
Charming house located in the heart of downtown Chatham!
3
2.0
8
Chatham Massachusetts Private vacation home
From $1127 per night
(USD)
5 Bdrm Spectacular Walk To Hardings Beach Ocean View Home
5
4.0
10
Chatham Massachusetts Private vacation home
From $885 per night
(USD)
Chatham Village: Large, Newly-Renovated 1 Bedroom Apartment in Antique Home
1
1.0
2
Chatham Massachusetts Apartment
From $340 per night
(USD)
Wonderful cottage located in the heart of downtown Chatham......steps to everything.
2
2.0
6
Chatham Massachusetts Cottage
From $873 per night
(USD)
Walk to private beach, central air, wifi, 3 bedrooms.
3
2.0
6
Chatham Massachusetts Cottage
From $858 per night
(USD)
Sunny Updated Chatham Village 2 Bedroom Condo W/ Large Private Deck
2
2.0
5
Chatham Massachusetts Condo
From $746 per night
(USD)
Sweet clapboard cottage that is walk to the beach and downtown!
1
1.0
2
Chatham Massachusetts Cottage
From $391 per night
(USD)
Cute clapboard cottage on the hill off Stage Island Road!
1
1.0
2
Chatham Massachusetts Cottage
From $396 per night
(USD)
Colorful clapboard cottage perfect for 2!
1
1.0
2
Chatham Massachusetts Cottage
From $420 per night
(USD)
Just off the Chatham bike loop... a perfect location for your family vacation.
2
2.0
6
Chatham Massachusetts Private vacation home
From $1052 per night
(USD)
5-Mins to Forest Beach Dog Friendly!
3
2.0
6
Chatham Massachusetts Private vacation home
From $438 per night
(USD)
Newly Renovated Modern Pond Access!
4
2.0
10
Chatham Massachusetts Private vacation home
From $482 per night
(USD)
Wrap-Around Porch Mins. to Beach!
2
1.0
6
South Chatham Massachusetts Private vacation home
From $319 per night
(USD)
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
5
3.0
10
Chatham Massachusetts Private vacation home
From $941 per night
(USD)
5BR-Beautiful Chatham-Year Round-Sleeps up to ten (10) & 1 Mile to Town!
5
2.0
10
Chatham Massachusetts Private vacation home
From $488 per night
(USD)
Sunrise to Sunset: Bucks Creek Retreat
3
2.0
8
South Chatham Massachusetts Private vacation home
From $738 per night
(USD)
Spacious Home on the Loop in Chatham
4
3.0
9
Chatham Massachusetts Private vacation home
From $1046 per night
(USD)
~ 4 Mi to Dtwn: Chatham Home w/ Fire Pit
3
2.0
8
South Chatham Massachusetts Private vacation home
From $446 per night
(USD)
Full Renovation! Amazing Spot with Views!
2
1.0
4
Chatham Massachusetts Condo
From $423 per night
(USD)
Beautiful Home w/ Artistic Flair!
3
3.0
7
Chatham Massachusetts Private vacation home
From $479 per night
(USD)
Centrally Located Home w/ Patio Fire Pit!
4
3.0
9
Chatham Massachusetts Private vacation home
From $611 per night
(USD)
Location and Luxury
3
3.0
6
Chatham Massachusetts Private vacation home
From $1352 per night
(USD)
Chatham walk to Cape Cod beach
3
2.0
8
Chatham Massachusetts Private vacation home
From $652 per night
(USD)
Charming Downtown Chatham
1
1.0
4
Chatham Massachusetts Condo
From $326 per night
(USD)
Chatham 3 Bedroom/2 Bath Retreat
3
2.0
6
Chatham Massachusetts Private vacation home
From $450 per night
(USD)
The Boarding House, King bed comfort. Close to Nantucket Sound beaches.
4
1.0
8
Chatham Massachusetts Private vacation home
From $711 per night
(USD)
Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views
2
1.0
5
Chatham Massachusetts Cottage
From $417 per night
(USD)
Charming Chatham Cottage!
3
3.0
8
Chatham Massachusetts Private vacation home
From $1675 per night
(USD)
Cozy Cape near Chatham Center
4
2.0
8
Chatham Massachusetts Private vacation home
From $653 per night
(USD)
Stylishly Furnished Home- Access to Pleasant Street Beach
2
2.0
8
Chatham Massachusetts Private vacation home
From $792 per night
(USD)
Spend your quintessential Cape Cod vacation, in a beautifully renovated 1862 Farm House on Stage Harbor Road!
6
6.0
13
Chatham Massachusetts Private vacation home
From $2106 per night
(USD)
Amazing Location! Lakefront Waterside Deck
4
2.0
8
Chatham Massachusetts Private vacation home
From $454 per night
(USD)
15 Minute Walk to Pleasant Street Beach!
4
2.0
8
South Chatham Massachusetts Private vacation home
From $409 per night
(USD)
Water View-Walk town/beach, pets considered, Linen Option
5
5.0
14
Chatham Massachusetts Private vacation home
From $976 per night
(USD)
Charming Chatham Home Close to Bassing Harbor!
4
2.0
8
North Chatham Massachusetts Private vacation home
From $902 per night
(USD)
Water Views in Chatham!
3
2.0
7
Chatham Massachusetts Private vacation home
From $991 per night
(USD)
Located in the heart of downtown Chatham, this gem offers an easy walk to everything.
4
2.0
8
Chatham Massachusetts Private vacation home
From $1427 per night
(USD)
Waterfront on Private Lake!
4
3.0
9
Chatham Massachusetts Private vacation home
From $450 per night
(USD)
Location, Location, Location!
3
2.0
8
South Chatham Massachusetts Private vacation home
From $325 per night
(USD)
Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!
2
2.0
3
Chatham Massachusetts Private vacation home
From $690 per night
(USD)
Cozy Chatham home with privacy and nautical decor
2
1.0
4
Chatham Massachusetts Private vacation home
From $699 per night
(USD)
Game Room Walk to Nantucket Sound!
4
3.0
10
South Chatham Massachusetts Private vacation home
From $496 per night
(USD)
Chatham-Walk to Ridgevale Beach, Winter Rental Option
3
2.0
9
Chatham Massachusetts Private vacation home
From $689 per night
(USD)
Stellar Home with Hot Tub & Movie Room!
4
2.0
10
Chatham Massachusetts Private vacation home
From $712 per night
(USD)
Lovely Home Minutes from Beach in Chatham!
3
1.0
6
Chatham Massachusetts Private vacation home
From $307 per night
(USD)
Stunning Water Views 2 Decks! By Beach!
4
2.0
8
Chatham Massachusetts Private vacation home
From $669 per night
(USD)
Central AC Close to Beach Dog Friendly!
3
1.0
8
Chatham Massachusetts Private vacation home
From $452 per night
(USD)
Walk to Ridgevale Beach!
2
1.0
4
Chatham Massachusetts Private vacation home
From $480 per night
(USD)
Located on Rail Trail By Beach & Downtown!
4
2.0
8
Chatham Massachusetts Private vacation home
From $536 per night
(USD)
4BR+Loft Beautiful Chatham-Year Round-Sleeps up to 8 & 1 Mile to Town **Video**
4
2.0
8
Chatham Massachusetts Private vacation home
From $550 per night
(USD)
Old Cape Cod Charm in Chatham MA, 1/4 mile Walking Distance to Hardings Beach
3
1.0
6
Chatham Massachusetts Private vacation home
From $307 per night
(USD)
Cozy Cockle Cove Retreat!
2
1.0
6
South chatham Massachusetts Private vacation home
From $713 per night
(USD)
Beautifully Renovated w/ Access to Beach!
6
4.0
14
North Chatham Massachusetts Private vacation home
From $823 per night
(USD)
Chatham Luxury! WALK to beach
2
2.0
4
North Chatham Massachusetts Condo
Click For Pricing
Great Location in Chatham Walk to town shop, dine, band concert, cape baseball
3
1.0
6
Chatham Massachusetts Private vacation home
From $439 per night
(USD)
Easy Bike Path Access, Dog Welcome!
3
2.0
6
Chatham Massachusetts Private vacation home
From $350 per night
(USD)
Great Chatham Location w/ Hot Tub, Near Beach!
3
2.0
8
North Chatham Massachusetts Private vacation home
From $604 per night
(USD)
WALK TO RESTAURANTS, SHOPS & LIQUOR STORE! CLOSE TO DOWNTOWN CHATHAM!
3
1.0
6
Chatham Massachusetts Cottage
From $347 per night
(USD)
Great Location Outdoor Space Dog Friendly
4
3.0
10
Chatham Massachusetts Private vacation home
From $516 per night
(USD)
5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet
5
2.0
10
Chatham Massachusetts Private vacation home
From $621 per night
(USD)
Hot Tub, Fenced Yard & Dog Friendly
3
2.0
8
North Chatham Massachusetts Private vacation home
From $711 per night
(USD)
Fully Updated Home w/ Great Outdoor Space!
2
1.0
4
South Chatham Massachusetts Private vacation home
From $291 per night
(USD)
Walk to the beach! The Salty Breeze sleeps 10; updated house, bikes, beach toys!
3
2.0
8
Chatham Massachusetts Private vacation home
From $784 per night
(USD)
Spacious w/ Large Outdoor Area Fire Pit!
4
2.0
8
Chatham Massachusetts Private vacation home
From $491 per night
(USD)
Charming Walk to Beach Chatham-Bayview Cottage 3 BR--Central A/C; Wi-Fi
3
2.0
6
Chatham Massachusetts Private vacation home
From $654 per night
(USD)
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
3
2.0
8
Chatham Massachusetts Private vacation home
From $665 per night
(USD)
Chatham Village - Center - Main Street Center Area
3
1.0
6
Chatham Massachusetts Condo
From $476 per night
(USD)
South Chatham cottage walk to beaches, dining, tennis, shops, bike path.
2
1.0
4
Chatham Massachusetts Private vacation home
Click For Pricing
Walk to Downtown Chatham, Steps to Beach!
4
3.0
8
Chatham Massachusetts Private vacation home
From $664 per night
(USD)
Waterfront Home With Dock and Two Water Facing Decks! (2372)
3
2.0
8
Chatham Massachusetts Private vacation home
From $607 per night
(USD)
Beach Bag Ready & Friday to Friday Rental!
4
2.0
9
Chatham Massachusetts Private vacation home
From $502 per night
(USD)
Stunning Marsh Views, Near Pleasant Street Beach!
4
2.0
8
Chatham Massachusetts Private vacation home
From $540 per night
(USD)
Poppy's Place: Cape Escape for Family & Friends
4
3.0
10
Chatham Massachusetts Private vacation home
From $683 per night
(USD)
Slow M'Ocean – A Fresh Take on Cape Calm
3
3.0
8
Chatham Massachusetts Private vacation home
From $995 per night
(USD)
Beautiful sunsets and saltwater views from every room
5
4.0
12
North Chatham Massachusetts Private vacation home
Click For Pricing
Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham
3
1.0
7
Chatham Massachusetts Private vacation home
From $744 per night
(USD)
Luxury Waterfront with Game Room!
5
3.0
12
Chatham Massachusetts Private vacation home
From $880 per night
(USD)
Elbow Inn: Private Retreat with Two Master Suites
4
3.0
8
Chatham Massachusetts Private vacation home
From $908 per night
(USD)
Coastal Retreat Minutes from Hardings Beach!
3
4.0
8
Chatham Massachusetts Private vacation home
From $1992 per night
(USD)
Mooncusser Cottage – A Charming Waterfront Escape
2
1.0
6
S. Chatham Massachusetts Cottage
From $938 per night
(USD)
Load More Results