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

Holiday Rentals in Chatham

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Our top choices for Chatham holiday rentals

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
9.8 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 €464
includes taxes & fees
13 Oct - 14 Oct
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

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 €469
includes taxes & fees
12 Oct - 13 Oct
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

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

4. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, Exceptional, (92 reviews)
"Beautiful, clean home with very responsive and kind hosts!"
United States
Claire D.
Beautiful home near Jacknife Beach and bike trail

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

6. 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 €446
includes taxes & fees
27 Oct - 28 Oct
Cozy Large Home in Harwich with Patio near Wequassett Resort

7. 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 €292
includes taxes & fees
20 Oct - 21 Oct
Brewster Green Resort

8. Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Dennis Port
9.2 out of 10, Wonderful, (27 reviews)
"Property is convenient to beaches and restaurants."
United States
Laurie and Rick A.
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

9. 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, (206 reviews)
The price is €280
includes taxes & fees
14 Oct - 15 Oct
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

10. 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.
Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard

11. 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.
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

12. 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 Brewster Pearl

13. 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 €413
includes taxes & fees
19 Oct - 20 Oct
On Town Cove with salt water access! Kayaks and paddle board available for use!

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

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, (29 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 €464
includes taxes & fees
8 Nov - 9 Nov
The Pet-Friendly Surf Shack Hideaway on the Cove

16. 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.
Seaside Escape-Art-filled 2 Bd on Town Cove

17. 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 €721
includes taxes & fees
9 Oct - 10 Oct
Family Cottage Close to Beach!!

18. 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 €131
includes taxes & fees
1 Nov - 2 Nov
The Cove at Yarmouth by Westgate Resorts

19. Cape Cod's "Beach Rose"

Cape Cod's "Beach Rose"
Dennis
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful home very easy check in and out host was great will definitely be staying their again in the future"
United States
Rachael M.
Cape Cod's "Beach Rose"
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

Everything you need to know about Chatham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chatham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chatham holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chatham holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chatham. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chatham holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chatham holiday rentals we have selected for you start as low as €131 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chatham rentals

At Expedia, we put the best Chatham holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chatham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chatham holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chatham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.