A boat on a calm river, a large house with a red roof, and dense greenery in the background.

Chatham Vacation Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Chatham vacation rentals

A living room with a white cabinet, striped armchair, and a wicker chair.

1. Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Chatham
10.0 out of 10, Exceptional, (128 reviews)
"Our stay was wonderful!"
United States
Corinne J.
The price is AED 826
AED 2,026 total
includes taxes & fees
2 Nov - 3 Nov
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
A deck with outdoor furniture including a sofa, chairs, and a table.

2. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, Exceptional, (94 reviews)
"Beautiful, clean home with very responsive and kind hosts!"
United States
Claire D.
The price is AED 992
AED 2,257 total
includes taxes & fees
1 Nov - 2 Nov
Beautiful home near Jacknife Beach and bike trail
A room with a blue sofa, wicker chairs, a round table, a wall-mounted lamp, and a glass door leading outside.

3. Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Chatham
9.6 out of 10, Exceptional, (108 reviews)
"Excellent location and stay at the lucky 7 cottage. The communication with the host was outstanding, best I’ve experienced. We’ll definitely be back for another time at this location."
United States
Mark K.
The price is AED 531
AED 2,067 total
includes taxes & fees
1 Nov - 2 Nov
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
A two-story house with a covered porch and a stone staircase leading to the entrance.

4. Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room

Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Chatham
10.0 out of 10, Exceptional, (24 reviews)
"House was wonderful with plenty of room. Great outdoor spaces with a deck and patio. Very convenient location. Host responsive to our needs. Would definitely stay again. "
United States
Sally S.
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
A spacious living area with a large window, a wooden ceiling, a television, and a sofa.

5. Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
Chatham
10.0 out of 10, Exceptional, (2 reviews)
"Lovely spot on the water!"
United States
Elizabeth T.
The price is AED 596
AED 1,991 total
includes taxes & fees
31 Oct - 1 Nov
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
A large outdoor swimming pool surrounded by lounge chairs and umbrellas, with a clear sky above.

6. Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
Brewster
10.0 out of 10, Exceptional, (54 reviews)
"Great stay!"
United States
Rebecca R.
The price is AED 658
AED 1,207 total
includes taxes & fees
1 Nov - 2 Nov
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
A two-story house with a front porch, a chimney, and a well-maintained lawn.

7. Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (83 reviews)
"Everything was exactly as described - they provided beach towels and chairs which we used - the property was perfect for our stay"
United States
John N.
The price is AED 1,157
AED 3,002 total
includes taxes & fees
31 Oct - 1 Nov
Family Cottage Close to Beach!!
A dining area with a table and four chairs, a painting of a beach scene, and a door in the background.

8. Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard

Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard
Harwich
10.0 out of 10, Exceptional, (11 reviews)
"Excellent location "
United States
Norman Y.
The price is AED 621
AED 2,224 total
includes taxes & fees
31 Oct - 1 Nov
Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard
A pool area with lounge chairs and flags.

9. The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts
3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (270 reviews)
"The property is an older timeshare and dated."
United States
Kim
The price is AED 395
AED 452 total
includes taxes & fees
1 Nov - 2 Nov
The Cove at Yarmouth by Westgate Resorts
A living room with a fireplace, a sofa, a coffee table, and a television.

10. The Brewster Pearl

The Brewster Pearl
Brewster
10.0 out of 10, Exceptional, (3 reviews)
"The home is so beautiful and the decor is like out of a magazine. Immaculately clean, our standards are high, being hosts ourselves. Every amenity thoughtfully provided. The furnishings, bedding, towels are of premium quality and top brand. Our host was incredible, responsive, kind and helpful. This home is perfectly located to many beaches , excellent restaurants and coffee shops. Brewster is a special place. I can understand why the owner chose it. Our family was immensely blessed to have the...
United States
PAULA
The price is AED 735
AED 2,392 total
includes taxes & fees
1 Nov - 2 Nov
The Brewster Pearl
A bedroom with a bed, a desk, a chair, a TV, and a window.

11. Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays

Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
Harwich
9.8 out of 10, Exceptional, (8 reviews)
"We loved staying at this beautiful house in Harwich. The property was clean, cozy and felt just like home. There was a fenced in back yard which was perfect for our dog and kids. Very private and close to shops, restaurants and the beach. We look forward to visiting again in the future!"
United States
Nicole M.
The price is AED 909
AED 1,389 total
includes taxes & fees
1 Nov - 2 Nov
Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
A spacious living room with a large sliding glass door leading to an outdoor patio, a ceiling fan, and a white sofa with patterned cushions.

12. Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
West Brewster
10.0 out of 10, Exceptional, (38 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is AED 731
AED 2,879 total
includes taxes & fees
1 Nov - 2 Nov
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
A modern kitchen with white cabinets, a central island, and a dining area with a table set for four.

13. Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge

Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
Orleans
9.8 out of 10, Exceptional, (18 reviews)
"Great house, so much room! We enjoyed our stay!!"
United States
Gina M.
The price is AED 6,611
AED 11,522 total
includes taxes & fees
31 Oct - 1 Nov
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
A residential backyard with a white fence, outdoor seating, and a house in the background.

14. Seaside Getaway - Harwichport Beachhouse

Seaside Getaway - Harwichport Beachhouse
Harwich
9.2 out of 10, Wonderful, (19 reviews)
"Great stay! Clean and comfortable and close to town."
United States
Meredith R.
The price is AED 757
AED 1,615 total
includes taxes & fees
2 Nov - 3 Nov
Seaside Getaway - Harwichport Beachhouse
A living room with a fireplace, sofas, a coffee table, and a television.

15. 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Dennis
10.0 out of 10, Exceptional, (209 reviews)
"Great location and perfect home for overnight stay!"
United States
Betsy D.
The price is AED 327
AED 1,144 total
includes taxes & fees
7 Nov - 8 Nov
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
A dining area with a table set for two, a chair, and a plant with pink flowers.

16. Beach Walks, Books & Bay Sunsets

Beach Walks, Books & Bay Sunsets
Brewster
10.0 out of 10, Exceptional, (3 reviews)
"The property was very clean, lots of little excellent touches, and amazing views. We truly enjoyed the pathway to the private beach. I wished we could have stayed longer. We will definitely be booking again."
United States
Sandra G.
The price is AED 688
AED 2,103 total
includes taxes & fees
2 Nov - 3 Nov
Beach Walks, Books & Bay Sunsets
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a central island with bar stools.

17. 2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.

2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.
Eastham
10.0 out of 10, Exceptional, (49 reviews)
"Kitchen was well equipped. Very good location for us and comfy beds. I highly recommend this property and the host. "
United States
Mark T R.
The price is AED 1,570
AED 3,735 total
includes taxes & fees
7 Nov - 8 Nov
2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.
A modern kitchen with white cabinets, a wooden ceiling, and a herringbone-patterned floor.

18. Beach Bungalow: Steps to Beach, Luxury Family Fun

Beach Bungalow: Steps to Beach, Luxury Family Fun
Harwich
10.0 out of 10, Exceptional, (10 reviews)
"We had an excellent stay on the cape at this beautiful home that was walking distance to the beach. The location was perfect and neighborhood was exactly what we dreamed of for an offseason getaway."
United States
Christopher R.
The price is AED 784
AED 2,225 total
includes taxes & fees
10 Nov - 11 Nov
Beach Bungalow: Steps to Beach, Luxury Family Fun
A living room with a grey sofa, striped rug, and a lamp.

19. The Pet-Friendly Surf Shack Hideaway on the Cove

The Pet-Friendly Surf Shack Hideaway on the Cove
Eastham
10.0 out of 10, Exceptional, (30 reviews)
"We had such a wonderful time at the Surf Shack. The location was perfect. Within 15 minutes the best beaches, best dining, best shopping..everything. The house was incredibly clean with all the amenities needed to have a great family vacation. The host was incredibly quick to reply to any and all inquiries and was so pleasant to deal with. We couldn’t be any happier with our stay and will definitely stay there again if our travels return us to the Cape."
United States
Justin R.
The price is AED 563
AED 1,843 total
includes taxes & fees
2 Nov - 3 Nov
The Pet-Friendly Surf Shack Hideaway on the Cove
A wooden deck with a ceiling fan, a sofa, and chairs.

20. Lovely House 5 Min to Beach with Deck, Grill, Garage

Lovely House 5 Min to Beach with Deck, Grill, Garage
Eastham
10.0 out of 10, Exceptional, (4 reviews)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is AED 518
AED 1,749 total
includes taxes & fees
1 Nov - 2 Nov
Lovely House 5 Min to Beach with Deck, Grill, Garage
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chatham Hotel Reviews

Hyannis Travel Inn

Hyannis Travel Inn

10/10 Excellent
"N/a"
Mary 2-night trip
Posted 15 hours ago
Hyannis Travel Inn

Frequently asked questions

Can I find a vacation rental in Chatham?

Yes, you can find vacation rentals in Chatham close to Chatham Railroad Museum, or you can select a more secluded option if you'd like a relaxing place to stay. Visitors like the popular beaches and waterfront in Chatham. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best vacation rentals that Chatham has to offer?

Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!: You might want to consider this vacation rental near Chatham, which is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade game room.

How many vacation rentals are there in Chatham?

With 277 Expedia vacation rentals, you're sure to find just the right place for your Chatham stay.

What can I see and do in Chatham?

Cultural attractions include Chatham Railroad Museum and Chatham Drama Guild, whereas Chatham Lighthouse Beach and Ridgevale Beach are a couple of picturesque spots to enjoy the outdoors. While here, Chatham Lighthouse and Cape Cod Beaches are other places worth a visit.

What are vacation rentals like in Chatham?

Vacation rentals are privately owned properties you can stay in for several days or longer in Chatham. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.