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

Chatham Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chatham holiday rentals

A room with a blue sofa, wicker chairs, a round table, a wall-mounted lamp, and a glass door leading outside.

1. 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, (107 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 HK$746
HK$4,011 total
includes taxes & fees
13 Oct - 14 Oct
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
A spacious living area with a large window, a wooden ceiling, a television, and a sofa.

2. 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 HK$965
HK$3,964 total
includes taxes & fees
13 Oct - 14 Oct
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
A lighthouse with a cylindrical tower and a white building with a red roof.

3. 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)
"Amazing stay so close to town and CBI."
United States
Joanne B.
The price is HK$1,766
HK$4,329 total
includes taxes & fees
2 Nov - 3 Nov
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
A sandy beach with a grassy path leading to the water.

4. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, Exceptional, (93 reviews)
"Beautiful, clean home with very responsive and kind hosts!"
United States
Claire D.
The price is HK$2,119
HK$4,823 total
includes taxes & fees
1 Nov - 2 Nov
Beautiful home near Jacknife Beach and bike trail
A two-story house with a covered porch and a stone staircase leading to the entrance.

5. 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, (23 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.
The price is HK$9,584
HK$12,532 total
includes taxes & fees
20 Oct - 21 Oct
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
A spacious living room with a large abstract painting, two chandeliers, and a coffee machine.

6. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (151 reviews)
"Very spacious rooms clean ,great location friendly staff,"
United States
Margaret
The price is HK$2,253
HK$2,579 total
includes taxes & fees
13 Oct - 14 Oct
Brewster Green Resort
A resort with a large pool, sun loungers, and a pier extending into the water.

7. Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
9.8 out of 10, Exceptional, (14 reviews)
"Great host. Convenient location for a visit to Chatham."
United States
Bill F.
The price is HK$1,099
HK$3,903 total
includes taxes & fees
27 Oct - 28 Oct
Cozy Large Home in Harwich with Patio near Wequassett Resort
An outdoor dining area with white chairs and umbrellas, overlooking the ocean.

8. 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, (207 reviews)
"Great location and great host!! We’ll be back!!!"
United States
Patrick T.
The price is HK$671
HK$2,403 total
includes taxes & fees
14 Oct - 15 Oct
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
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, (269 reviews)
"The property is an older timeshare and dated."
United States
Kim
The price is HK$1,011
HK$1,157 total
includes taxes & fees
1 Nov - 2 Nov
The Cove at Yarmouth by Westgate Resorts
A beach with people, tents, and umbrellas.

10. 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, (52 reviews)
"We did a quick overnight The amenities were great and the condo was perfect !!!"
United States
Katie M.
The price is HK$1,562
HK$2,793 total
includes taxes & fees
1 Nov - 2 Nov
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
An outdoor patio with Adirondack chairs, a fire pit, and string lights.

11. 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 HK$1,648
HK$5,003 total
includes taxes & fees
13 Oct - 14 Oct
Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard
A wide sandy beach with gentle waves and a clear blue sky.

12. On Town Cove with salt water access! Kayaks and paddle board available for use!

On Town Cove with salt water access! Kayaks and paddle board available for use!
Eastham
9.8 out of 10, Exceptional, (68 reviews)
"Clean, great location. "
United States
Peter G.
The price is HK$1,295
HK$3,521 total
includes taxes & fees
19 Oct - 20 Oct
On Town Cove with salt water access! Kayaks and paddle board available for use!
A beach with footprints, a large rock, and a clear sky.

13. 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 HK$1,687
HK$5,290 total
includes taxes & fees
26 Oct - 27 Oct
The Brewster Pearl
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.

14. 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, (37 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is HK$1,361
HK$5,886 total
includes taxes & fees
14 Oct - 15 Oct
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
A 'Welcome to Your Beach House' sign and a woven beach hat on the wall.

15. 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 HK$1,212
HK$3,973 total
includes taxes & fees
26 Oct - 27 Oct
The Pet-Friendly Surf Shack Hideaway on the Cove
A beach with a wooden walkway and a fence leading to a building.

16. 🐚The Bay Cottage on Thumpertown Beach

🐚The Bay Cottage on Thumpertown Beach
Eastham
9.8 out of 10, Exceptional, (14 reviews)
"My group and I had another wonderful stay at the Bay Cottage! The space is sparkling clean when we arrived and the location cannot be beat. Tara is also very responsive and attentive which makes for an even better stay!"
United States
Sophia I.
The price is HK$1,160
HK$3,088 total
includes taxes & fees
13 Oct - 14 Oct
🐚The Bay Cottage on Thumpertown Beach
A wooden deck with a view of a lake, surrounded by trees.

17. Pondside/Kayak/Firepit/Dog Friendly~Willow Haven

Pondside/Kayak/Firepit/Dog Friendly~Willow Haven
Eastham
9.8 out of 10, Exceptional, (8 reviews)
"Great hideaway location on the Cape. Well equipped rental."
United Kingdom
Richard F.
The price is HK$1,066
HK$2,971 total
includes taxes & fees
18 Oct - 19 Oct
Pondside/Kayak/Firepit/Dog Friendly~Willow Haven
A patio with two striped lounge chairs, a small round table, and two blue glass candle holders.

18. Seaside Escape-Art-filled 2 Bd on Town Cove

Seaside Escape-Art-filled 2 Bd on Town Cove
EASTHAM
7.4 out of 10, Good, (3 reviews)
"The cottage was very well decorated, maintained and well stocked. Loved the location with a view of the cove.My kids loved the loft"
United States
Myriam A.
The price is HK$1,332
HK$4,102 total
includes taxes & fees
13 Oct - 14 Oct
Seaside Escape-Art-filled 2 Bd on Town Cove
A metal showerhead attached to a house's exterior wall, with water flowing down a blue gutter.

19. Captain's Quarters by Nauset Beach

Captain's Quarters by Nauset Beach
East Orleans
10.0 out of 10, Exceptional, (12 reviews)
"It is a beautiful property."
United States
Phillip B.
The price is HK$1,469
HK$4,412 total
includes taxes & fees
13 Oct - 14 Oct
Captain's Quarters by Nauset Beach
A table set outdoors with a view of a lake, surrounded by trees.

20. 🦀Waterfront at The Velvet Crab~Amazing Sunsets

🦀Waterfront at The Velvet Crab~Amazing Sunsets
Eastham
9.8 out of 10, Exceptional, (28 reviews)
"Perfect size home for a family of 4, welcoming and cozy! Having -All towels and linens and shampoo, body wash and conditioner all included made for a much easier stay! Highly recommend."
United States
Emily A.
The price is HK$1,186
HK$3,423 total
includes taxes & fees
18 Oct - 19 Oct
🦀Waterfront at The Velvet Crab~Amazing Sunsets
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

Lighthouse Inn

Lighthouse Inn

8/10 Good
"Beautiful property, view of the ocean. Fireplace is very nice amenity."
David 2-night trip
Posted 2 hours ago
Lighthouse Inn

Find out more about Chatham

Search for holiday rentals in Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in Chatham using one of the methods below:

  • View our selection of featured holiday rentals in Chatham
  • Use the map to find apartments and other holiday homes in the Chatham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chatham while they last

Look no further and take a look at our great range of rental properties in Chatham!

Frequently asked questions

Can I find a holiday rental in Chatham?

Yes, there are holiday rentals in Chatham close to Chatham Railroad Museum, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Chatham has to offer?

Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!: This holiday home rental outside of Chatham is located on the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade/games room.

How many holiday rentals are there in Chatham?

With 277 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Chatham?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chatham. Holiday rentals offer extras such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.