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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Our top choices for Chatham vacation 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, (2 reviews)
"Lovely spot on the water!"
United States
Elizabeth T.
The price is ¥19,345
¥75,840 total
includes taxes & fees
Sep 29 - Sep 30
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)
"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 ¥14,942
¥74,809 total
includes taxes & fees
Oct 12 - Oct 13
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

3. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, Exceptional, (90 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 ¥42,466
¥91,084 total
includes taxes & fees
Sep 29 - Sep 30
Beautiful home near Jacknife Beach and bike trail

4. 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 ¥37,354
¥83,973 total
includes taxes & fees
Oct 4 - Oct 5
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

5. 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
Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach

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, (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 ¥190,529
¥235,340 total
includes taxes & fees
Oct 27 - Oct 28
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room

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 ¥19,110
¥69,966 total
includes taxes & fees
Sep 29 - Sep 30
Cozy Large Home in Harwich with Patio near Wequassett Resort

8. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (146 reviews)
"Very spacious rooms clean ,great location friendly staff,"
United States
Margaret
The price is ¥34,072
¥38,995 total
includes taxes & fees
Oct 5 - Oct 6
Brewster Green 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 traveler
The price is ¥39,320
¥70,204 total
includes taxes & fees
Sep 29 - Sep 30
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 ¥34,602
¥99,905 total
includes taxes & fees
Sep 29 - Sep 30
Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

11. 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, (35 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is ¥36,363
¥122,261 total
includes taxes & fees
Oct 1 - Oct 2
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

12. 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 ¥49,543
¥119,886 total
includes taxes & fees
Sep 29 - Sep 30
Family Cottage Close to Beach!!

13. 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 ¥35,388
¥52,752 total
includes taxes & fees
Sep 29 - Sep 30
The Beachcomber Unit - #9

14. 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 ¥25,637
¥65,165 total
includes taxes & fees
Oct 20 - Oct 21
On Town Cove with salt water access! Kayaks and paddle board available for use!

15. Relaxing Cape Escape • Family Retreat • Walk to Beach • 6 beds • Sleeps 8

Relaxing Cape Escape • Family Retreat • Walk to Beach • 6 beds • Sleeps 8
Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Great house in a wonderful location! Would definitely stay again!"
United States
Kelly M.
The price is ¥75,337
¥150,305 total
includes taxes & fees
Oct 5 - Oct 6
Relaxing Cape Escape • Family Retreat • Walk to Beach • 6 beds • Sleeps 8

16. Cape Cod Oceanside Condo across from beach!

Cape Cod Oceanside Condo across from beach!
Dennis
9.0 out of 10, Wonderful, (24 reviews)
"We had a wonderful stay! The place was very clean and fit 3 people comfortably. We loved having the beach right across the street. The check in process was very easy and the front desk staff was super nice! Would definitely stay here again!!"
United States
Lindsey Y.
The price is ¥15,728
¥21,601 total
includes taxes & fees
Oct 7 - Oct 8
Cape Cod Oceanside Condo across from beach!

17. 🌊The Ocean Cottage on Thumpertown Beach

🌊The Ocean Cottage on Thumpertown Beach
Eastham
9.4 out of 10, Exceptional, (13 reviews)
"We absolutely loved the place and the location right near Thumpertown Beach was perfect!"
United States
Jeff P.
The price is ¥23,251
¥58,293 total
includes taxes & fees
Oct 27 - Oct 28
🌊The Ocean Cottage on Thumpertown Beach

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 ¥29,451
¥83,209 total
includes taxes & fees
Oct 5 - Oct 6
Captain's Quarters by Nauset Beach

19. 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!

20. 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, (205 reviews)
"Great location and great host!! We’ll be back!!!"
United States
Patrick T.
The price is ¥14,942
¥47,703 total
includes taxes & fees
Oct 14 - Oct 15
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
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

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:

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

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.