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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Our top choices for Chatham holiday rentals

1. 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, (1 review)
"Lovely spot on the water!"
United States
Elizabeth T.
The price is NZ$897
includes taxes & fees
27 Sept - 28 Sept
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

2. 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
9.8 out of 10, Exceptional, (106 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is NZ$889
includes taxes & fees
7 Oct - 8 Oct
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

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, (127 reviews)
"Amazing stay so close to town and CBI."
United States
Joanne B.
The price is NZ$984
includes taxes & fees
20 Oct - 21 Oct
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

4. Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach

Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach
Chatham
9.8 out of 10, Exceptional, (8 reviews)
"Lock didn’t work"
United States
Claudine
The price is NZ$1,356
includes taxes & fees
22 Sept - 23 Sept
Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach

5. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, Exceptional, (88 reviews)
"This is second time to stay here! We love the location and hospitality of the hosts! Great place!"
United States
Barbara P.
The price is NZ$1,036
includes taxes & fees
5 Oct - 6 Oct
Beautiful home near Jacknife Beach and bike trail

6. 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, (22 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 NZ$2,342
includes taxes & fees
20 Oct - 21 Oct
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room

7. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (146 reviews)
"We stay here every year! Love it!"
United States
Karel
The price is NZ$438
includes taxes & fees
24 Sept - 25 Sept
Brewster Green Resort

8. 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 NZ$862
includes taxes & fees
28 Sept - 29 Sept
Cozy Large Home in Harwich with Patio near Wequassett Resort

9. Quiet getaway in a unique area of Cape Cod

Quiet getaway in a unique area of Cape Cod
Brewster
10.0 out of 10, Exceptional, (5 reviews)
"Perfect for a quiet getaway. Owner was in Constant contact. If I had a question replied very quickly. I highly recommend staying here."
United States
Anonymous traveller
The price is NZ$802
includes taxes & fees
21 Sept - 22 Sept
Quiet getaway in a unique area of Cape Cod

10. Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
Harwich
10.0 out of 10, Exceptional, (10 reviews)
"Excellent location "
United States
Norman Y.
The price is NZ$1,186
includes taxes & fees
21 Sept - 22 Sept
Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

11. Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (82 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 NZ$1,402
includes taxes & fees
21 Sept - 22 Sept
Family Cottage Close to Beach!!

12. The Beachcomber Unit - #9

The Beachcomber Unit - #9
Harwich
10.0 out of 10, Exceptional, (21 reviews)
"We had an amazing time staying here, great location and it was very clean. "
United States
Mike B.
The price is NZ$520
includes taxes & fees
23 Sept - 24 Sept
The Beachcomber Unit - #9

13. Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, Exceptional, (52 reviews)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is NZ$1,085
includes taxes & fees
22 Sept - 23 Sept
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

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, (33 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is NZ$1,349
includes taxes & fees
22 Sept - 23 Sept
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

15. Newly Refreshed Upscale Cottage/Pvt 2 KING BR Ensuite /1 Mile to Hardings Beach

Newly Refreshed Upscale Cottage/Pvt 2 KING BR Ensuite /1 Mile to Hardings Beach
Chatham
10.0 out of 10, Exceptional, (20 reviews)
"Everything exceeded expectations"
United States
Marc S.
The price is NZ$2,131
includes taxes & fees
3 Oct - 4 Oct
Newly Refreshed Upscale Cottage/Pvt 2 KING BR Ensuite /1 Mile to Hardings Beach

16. 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, (66 reviews)
"Clean, great location. "
United States
Peter G.
The price is NZ$804
includes taxes & fees
19 Oct - 20 Oct
On Town Cove with salt water access! Kayaks and paddle board available for use!

17. Harwich Hideaway with King Beds Pet Friendly!

Harwich Hideaway with King Beds Pet Friendly!
Harwich
8.8 out of 10, Excellent, (5 reviews)
"Dog friendly property!"
United States
Colleen O.
Harwich Hideaway with King Beds Pet Friendly!

18. Captain's Quarters by Nauset Beach

Captain's Quarters by Nauset Beach
East Orleans
10.0 out of 10, Exceptional, (12 reviews)
"Cape Cod cottage close to the beach."
United States
Bill B.
The price is NZ$945
includes taxes & fees
5 Oct - 6 Oct
Captain's Quarters by Nauset Beach

19. 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, (51 reviews)
"We did a quick overnight The amenities were great and the condo was perfect !!!"
United States
Katie M.
The price is NZ$736
includes taxes & fees
12 Oct - 13 Oct
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

20. Cape Cod Villa pond front vacation home, retreat, spa, venue, film location

Cape Cod Villa pond front vacation home, retreat, spa, venue, film location
Harwich - Brewster Border
10.0 out of 10, Exceptional, (8 reviews)
"Such an awesome stay for my best friends bachelorette party! 20/10 would recommend and would stay there again."
United States
Emma S.
The price is NZ$1,662
includes taxes & fees
6 Oct - 7 Oct
Cape Cod Villa pond front vacation home, retreat, spa, venue, film location
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

Find out more about Chatham

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chatham holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chatham. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chatham. Seeing all the best attractions is bound to make you fall in love with Chatham. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chatham short-term rentals, that won’t be hard to do.

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 274 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.