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Chatham Vacation Rentals

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Check prices for these dates

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

Our top choices for Chatham vacation 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.
$482 nightly
The price is $552
Nov 2 - Nov 3
Total with taxes and fees
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.
$416 nightly
The price is $476
Oct 18 - Oct 19
Total with taxes and fees
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.
$537 nightly
The price is $615
Nov 1 - Nov 2
Total with taxes and fees
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.
$420 nightly
The price is $481
Oct 18 - Oct 19
Total with taxes and fees
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.
$1,501 nightly
The price is $1,718
Nov 2 - Nov 3
Total with taxes and fees
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, (152 reviews)
"Very spacious rooms clean ,great location friendly staff,"
United States
Margaret
$345 nightly
The price is $394
Nov 15 - Nov 16
Total with taxes and fees
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.
$714 nightly
The price is $817
Oct 17 - Oct 18
Total with taxes and fees
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
$105 nightly
The price is $120
Nov 2 - Nov 3
Total with taxes and fees
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.
$449 nightly
The price is $497
Oct 27 - Oct 28
Total with taxes and fees
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.
$545 nightly
The price is $624
Oct 19 - Oct 20
Total with taxes and fees
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)
"We did a quick overnight The amenities were great and the condo was perfect !!!"
United States
Katie M.
$311 nightly
The price is $356
Nov 1 - Nov 2
Total with taxes and fees
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.
$457 nightly
The price is $523
Oct 18 - Oct 19
Total with taxes and fees
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.
$655 nightly
The price is $750
Oct 18 - Oct 19
Total with taxes and fees
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.
$373 nightly
The price is $426
Oct 21 - Oct 22
Total with taxes and fees
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
$589 nightly
The price is $674
Nov 1 - Nov 2
Total with taxes and fees
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.
$491 nightly
The price is $562
Oct 19 - Oct 20
Total with taxes and fees
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.
$435 nightly
The price is $498
Oct 19 - Oct 20
Total with taxes and fees
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.
$889 nightly
The price is $1,017
Oct 17 - Oct 18
Total with taxes and fees
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.
$559 nightly
The price is $640
Oct 19 - Oct 20
Total with taxes and fees
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.
$2,227 nightly
The price is $2,549
Oct 17 - Oct 18
Total with taxes and fees
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 8 hours ago
Hyannis Travel Inn

Find out more about Chatham

Everything you need to know about Chatham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chatham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chatham vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chatham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $120 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chatham rentals

At Expedia, we put the best Chatham vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.