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

Chatham Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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.
$502 nightly
The price is $575
Oct 7 - Oct 8
Total with taxes and fees
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
welcome home to an open concept and clean canvas.

2. 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)
"The Cape Coddage was perfect! Great location, beautiful little cottage and great hosts! We will definitely be repeat customers in the future. Quintessential Cape Cod, don’t hesitate to give it a try!"
United States
Jason M.
$793 nightly
The price is $908
Oct 18 - Oct 19
Total with taxes and fees
Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach
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, (90 reviews)
"Beautiful, clean home with very responsive and kind hosts!"
United States
Claire D.
$537 nightly
The price is $615
Oct 5 - Oct 6
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
9.8 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.
$441 nightly
The price is $504
Oct 27 - Oct 28
Total with taxes and fees
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
A spacious living area with a large window, a wooden ceiling, a television, and a sofa.

5. 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.
$445 nightly
The price is $510
Oct 12 - Oct 13
Total with taxes and fees
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
A two-story house with a covered porch and a stone staircase leading to the entrance.

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.
$1,300 nightly
The price is $1,487
Oct 27 - Oct 28
Total with taxes and fees
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
A cozy interior with a wooden ceiling, white walls, and a white sofa with blue cushions. There is a wooden table and a blue chair.

7. 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.
$1,109 nightly
The price is $1,270
Oct 3 - Oct 4
Total with taxes and fees
Newly Refreshed Upscale Cottage/Pvt 2 KING BR Ensuite /1 Mile to Hardings Beach
sample of beautiful Cape Cod beaches

8. 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
$401 nightly
The price is $459
Oct 2 - Oct 3
Total with taxes and fees
Quiet getaway in a unique area of Cape Cod
A two-story house with a front porch, a chimney, and a well-maintained lawn.

9. 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.
$714 nightly
The price is $817
Oct 2 - Oct 3
Total with taxes and fees
Family Cottage Close to Beach!!
A resort with a large pool, sun loungers, and a pier extending into the water.

10. 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 5 - Oct 6
Total with taxes and fees
Cozy Large Home in Harwich with Patio near Wequassett Resort
A bathroom with a white vanity, a towel rack, and a television mounted on the wall.

11. The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (61 reviews)
"amazing location and cute place to stay!"
United States
Adriana A.
$266 nightly
The price is $297
Oct 2 - Oct 3
Total with taxes and fees
The Nantucket Room Unit - #2
A bed with a headboard, a bedside table with a bottle and glasses, and a window with a view of a building.

12. Paradise Palm Unit - #4

Paradise Palm Unit - #4
Harwich
9.8 out of 10, Exceptional, (34 reviews)
"A nice quiet place to stay. The rooms are well equipped."
United States
Daniel B.
$266 nightly
The price is $297
Oct 2 - Oct 3
Total with taxes and fees
Paradise Palm Unit - #4
Beach

13. Endless Summer Unit - #3

Endless Summer Unit - #3
Harwich
9.8 out of 10, Exceptional, (31 reviews)
"We have stayed here before and happy to be back! All the amenities and even a light breakfast in the morning! Great pool to relax in and close to restaurants and shops."
United States
Susan T.
$266 nightly
The price is $297
Oct 2 - Oct 3
Total with taxes and fees
Endless Summer Unit - #3
An outdoor patio with Adirondack chairs, a fire pit, and string lights.

14. 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, (11 reviews)
"Excellent location "
United States
Norman Y.
$623 nightly
The price is $713
Oct 4 - Oct 5
Total with taxes and fees
Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
Terrace/patio

15. 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.
$266 nightly
The price is $297
Oct 2 - Oct 3
Total with taxes and fees
The Beachcomber Unit - #9
A beach with people, tents, and umbrellas.

16. 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.
$313 nightly
The price is $358
Nov 1 - Nov 2
Total with taxes and fees
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
A beach with a rocky shoreline, clear blue sky, and houses in the background.

17. 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.
$888 nightly
The price is $1,016
Oct 8 - Oct 9
Total with taxes and fees
Relaxing Cape Escape • Family Retreat • Walk to Beach • 6 beds • Sleeps 8
A pool area with lounge chairs and flags.

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, (268 reviews)
"P Indoor pool and hot tub loved and the outdoor Shack was great"
United States
BELKIS
$114 nightly
The price is $131
Oct 25 - Oct 26
Total with taxes and fees
The Cove at Yarmouth by Westgate Resorts
A beach with a wooden walkway leading to the shore, a rocky breakwater, and a clear sky at sunset.

19. Seaside Getaway - Harwichport Beachhouse

Seaside Getaway - Harwichport Beachhouse
Harwich
9.2 out of 10, Wonderful, (17 reviews)
"Great stay! Clean and comfortable and close to town."
United States
Meredith R.
$425 nightly
The price is $487
Oct 2 - Oct 3
Total with taxes and fees
Seaside Getaway - Harwichport Beachhouse
A wide sandy beach with gentle waves and a clear blue sky.

20. 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.
$384 nightly
The price is $439
Oct 19 - Oct 20
Total with taxes and fees
On Town Cove with salt water access! Kayaks and paddle board available for use!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chatham Hotel Reviews

Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"Breakfast"
Melinda 1-night trip
Posted 1 hour ago
Bayside Resort Hotel

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 $131 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.