Chatham Vacation Rentals from $121: Search Short-Term Rentals

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Our top choices for Chatham vacation rentals

A spacious living area with a large window, a wooden ceiling, a television, and a sofa.

1. Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

Chatham

Elizabeth T.

$436 nightly

Oct 25 - Oct 26

Total with taxes and fees

A room with a blue sofa, wicker chairs, a round table, a wall-mounted lamp, and a glass door leading outside.

2. Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Chatham

Mark K.

$427 nightly

Oct 27 - Oct 28

Total with taxes and fees

A living room with a white cabinet, striped armchair, and a wicker chair.

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

Chatham

Corinne J.

$482 nightly

Nov 2 - Nov 3

Total with taxes and fees

A deck with outdoor furniture including a sofa, chairs, and a table.

4. Beautiful home near Jacknife Beach and bike trail

Chatham

Claire D.

$537 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

Chatham

Sally S.

$1,339 nightly

Oct 26 - Oct 27

Total with taxes and fees

A resort with a large pool, sun loungers, and a pier extending into the water.

6. Cozy Large Home in Harwich with Patio near Wequassett Resort

Harwich

Bill F.

$433 nightly

Oct 27 - Oct 28

Total with taxes and fees

A bathroom with a white vanity, a towel rack, and a television mounted on the wall.

7. The Nantucket Room Unit - #2

Harwich port

Adriana A.

$264 nightly

Oct 25 - Oct 26

Total with taxes and fees

An outdoor patio with Adirondack chairs, a fire pit, and string lights.

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

Harwich

Norman Y.

$532 nightly

Oct 25 - Oct 26

Total with taxes and fees

A bed with a headboard, a bedside table with a bottle and glasses, and a window with a view of a building.

9. Paradise Palm Unit - #4

Harwich

Daniel B.

$264 nightly

Oct 25 - Oct 26

Total with taxes and fees

10. Endless Summer Unit - #3

Harwich

Susan T.

$266 nightly

Oct 26 - Oct 27

Total with taxes and fees

A large outdoor swimming pool surrounded by lounge chairs and umbrellas, with a clear sky above.

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

Brewster

Rebecca R.

$289 nightly

Nov 1 - Nov 2

Total with taxes and fees

A residential backyard with a swimming pool, a patio with outdoor furniture, and a house with multiple windows and a covered porch.

12. Harbor Getaway Unit -1

Harwich

Ashley H.

$259 nightly

Oct 25 - Oct 26

Total with taxes and fees

A living room with a fireplace, sofas, a coffee table, and a television.

13. 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Dennis

Elayne F.

$270 nightly

Nov 7 - Nov 8

Total with taxes and fees

A pool area with lounge chairs and flags.

14. The Cove at Yarmouth by Westgate Resorts

West Yarmouth

Kim

$106 nightly

Nov 8 - Nov 9

Total with taxes and fees

A living room with a fireplace, a sofa, a coffee table, and a television.

15. The Brewster Pearl

Brewster

"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...

PAULA

$586 nightly

Oct 25 - Oct 26

Total with taxes and fees

A living room with a grey sofa, striped rug, and a lamp.

16. The Pet-Friendly Surf Shack Hideaway on the Cove

Eastham

"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."

Justin R.

$439 nightly

Oct 25 - Oct 26

Total with taxes and fees

A two-story house with a front porch, a chimney, and a well-maintained lawn.

17. Family Cottage Close to Beach!!

Harwichport

John N.

$707 nightly

Oct 25 - Oct 26

Total with taxes and fees

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.

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

West Brewster

Jim M.

$669 nightly

Oct 27 - Oct 28

Total with taxes and fees

A wooden deck with outdoor furniture, a covered seating area, and a view of neighboring houses.

19. Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

Dennis Port

Art E.

$383 nightly

Oct 25 - Oct 26

Total with taxes and fees

A patio with two striped lounge chairs, a small round table, and two blue glass candle holders.

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

EASTHAM

Myriam A.

$458 nightly

Oct 25 - Oct 26

Total with taxes and fees

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Top Chatham Hotel Reviews

The Hawthorne

10/10 Excellent

"An old motel with a great quiet location in Chatham. Nice big room with amazing view. Motel has beach access on the channel. Possible to walk to town but only 10 minutes by car. Management are most helpful and knowledgeable. Great place to stay."

Margaritaville Resort Cape Cod

8/10 Good

"Overall, the hotel and our room were lovely. There was a large event taking place during our stay, and a significant number of younger guests from the event were gathered throughout the public areas. While completely understandable, it did make it difficult for us to enjoy those spaces. Our only real disappointment was breakfast. We needed something quick and were directed to the to-go area, but waited more than 20 minutes for a simple breakfast sandwich. When it was made incorrectly, the interaction felt unnecessarily dismissive and we were made to feel as though the mistake was our fault. A little more customer-service-minded handling would have made a big difference. Aside from that experience, we had a lovely room and enjoyed our stay overall."

Old Harbor Inn

10/10 Excellent

"We thoroughly enjoyed or 25th anniversary weekend at the Old Harbor inn! The staff and owner’s were amazing. The inn was well maintained the atmosphere and amenities were on point. The room was super and clean. The breakfast was great. Thanks to all who made our stay very enjoyable! We will be recommending this inn to our friends."

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 $121 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.

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Things to do 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.

Room 1

Check prices for these dates

Our top choices for Chatham vacation rentals

1. 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

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

4. Beautiful home near Jacknife Beach and bike trail

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

6. Cozy Large Home in Harwich with Patio near Wequassett Resort

7. The Nantucket Room Unit - #2

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

9. Paradise Palm Unit - #4

10. Endless Summer Unit - #3

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

12. Harbor Getaway Unit -1

13. 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

14. The Cove at Yarmouth by Westgate Resorts

15. The Brewster Pearl

16. The Pet-Friendly Surf Shack Hideaway on the Cove

17. Family Cottage Close to Beach!!

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

19. Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

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

Find vacation rentals that suit your style

Top Chatham Hotel Reviews

The Hawthorne

Greyfinch Chatham Inn

Hyannis Travel Inn

Bayside Resort Hotel

Margaritaville Resort Cape Cod

Chatham Bars Inn

Old Harbor Inn

Cape Cod Family Resort and Parks

Find out more about Chatham

Explore a world of travel with Expedia

Frequently asked questions

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