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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 lighthouse with a cylindrical tower and a white building with a red roof.

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)
"Amazing stay so close to town and CBI."
United States
Joanne B.
The price is AU$764
includes taxes & fees
2 Nov - 3 Nov
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
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 AU$693
includes taxes & fees
18 Oct - 19 Oct
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
A sandy beach with a grassy path leading to the water.

3. 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 AU$846
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.

4. 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 AU$675
includes taxes & fees
18 Oct - 19 Oct
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.

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 AU$2,384
includes taxes & fees
2 Nov - 3 Nov
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
A recreational room with a foosball table, pool table, and a table tennis table. There are several chairs and a small bookshelf.

6. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (152 reviews)
"Very spacious rooms clean ,great location friendly staff,"
United States
Margaret
The price is AU$471
includes taxes & fees
3 Nov - 4 Nov
Brewster Green Resort
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 AU$1,144
includes taxes & fees
22 Oct - 23 Oct
Family Cottage Close to Beach!!
A pool area with lounge chairs and flags.

8. 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 AU$173
includes taxes & fees
1 Nov - 2 Nov
The Cove at Yarmouth by Westgate Resorts
A resort with a large pool, sun loungers, and a pier extending into the water.

9. 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 AU$692
includes taxes & fees
28 Oct - 29 Oct
Cozy Large Home in Harwich with Patio near Wequassett Resort
An outdoor patio with Adirondack chairs, a fire pit, and string lights.

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.
The price is AU$879
includes taxes & fees
20 Oct - 21 Oct
Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard
A beach with people, tents, and umbrellas.

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)
The price is AU$505
includes taxes & fees
1 Nov - 2 Nov
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
A bedroom with a bed, a desk, a chair, a TV, and a window.

12. 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, (7 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 AU$742
includes taxes & fees
18 Oct - 19 Oct
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.

13. 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 AU$1,072
includes taxes & fees
19 Oct - 20 Oct
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
A wide sandy beach with gentle waves and a clear blue sky.

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, (68 reviews)
"Clean, great location. "
United States
Peter G.
The price is AU$600
includes taxes & fees
21 Oct - 22 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.

15. 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 AU$947
includes taxes & fees
1 Nov - 2 Nov
The Brewster Pearl
A metal showerhead attached to a house's exterior wall, with water flowing down a blue gutter.

16. 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 AU$801
includes taxes & fees
22 Oct - 23 Oct
Captain's Quarters by Nauset Beach
A beach with a wooden walkway leading to the shore, a rocky breakwater, and a clear sky at sunset.

17. Seaside Getaway - Harwichport Beachhouse

Seaside Getaway - Harwichport Beachhouse
Harwich
9.0 out of 10, Wonderful, (18 reviews)
"Great stay! Clean and comfortable and close to town."
United States
Meredith R.
The price is AU$702
includes taxes & fees
22 Oct - 23 Oct
Seaside Getaway - Harwichport Beachhouse
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a central island with bar stools.

18. 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 AU$1,419
includes taxes & fees
22 Oct - 23 Oct
2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.
A sandy beach path leading to the ocean with a clear sky.

19. 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 AU$902
includes taxes & fees
19 Oct - 20 Oct
Beach Walks, Books & Bay Sunsets
A wooden deck with a fire pit, outdoor seating, and a pool area at dusk.

20. Private Heated Pool • 5BR/3BA • Near Beaches and Nickerson Park

Private Heated Pool • 5BR/3BA • Near Beaches and Nickerson Park
Brewster
9.8 out of 10, Exceptional, (61 reviews)
"Great place to stay with your family "
United States
Mary H.
The price is AU$3,433
includes taxes & fees
18 Oct - 19 Oct
Private Heated Pool • 5BR/3BA • Near Beaches and Nickerson Park
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

8/10 Good
"The room was clean but dated. The towels were aged the sheets were yellowed but it was definitely clean. The staff were pleasant, friendly and helpful. There is no elevator and the king beds are on the 3rd floor but the staff helped with our luggage. Parking was free and close by. This inn is within walking distance to the ship port for Martha’s Vineyard which was nice because it saved us from paying for parking. The air conditioning worked well as well as the heat. The breakfast was basic continental. The room came with a microwave and a large dorm sized refrigerator. Overall this is a basic friendly clean place to stop to visit nearby sites."
D 2-night trip
Posted 12 hours ago
Hyannis Travel Inn

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, 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 favourite 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 depend 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 AU$173 per night. Entering your travel dates in the search wizard might find you 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.