Chatham Vacation Rentals from ￥11,904: Search Short-Term Rentals

A lighthouse with a house nearby, under a starry night sky with visible Milky Way.

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Our top choices for Chatham vacation rentals

A sandy beach with a grassy path leading to the water.

1. Beautiful home near Jacknife Beach and bike trail

Chatham

Claire D.

￥92,827 total

includes taxes & fees

Nov 13 - Nov 14

A two-story house with a white picket fence, a chimney, and a driveway.

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

Chatham

Corinne J.

￥87,013 total

includes taxes & fees

Nov 18 - Nov 19

A single-story house with a grey roof, white trim, and a pink door.

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

Chatham

Jennifer B.

￥82,910 total

includes taxes & fees

Dec 7 - Dec 8

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

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

Harwich

Norman Y.

￥93,007 total

includes taxes & fees

Nov 13 - Nov 14

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

5. Family Cottage Close to Beach!!

Harwichport

Jennifer S.

￥123,346 total

includes taxes & fees

Nov 14 - Nov 15

A sandy beach with dunes and a clear sky.

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

Brewster

Rebecca R.

￥49,792 total

includes taxes & fees

Nov 18 - Nov 19

7. The Captain's Quarters Suite Unit - 10

Harwich

Annyck H.

￥44,897 total

includes taxes & fees

Nov 18 - Nov 19

A beachside seating area with Adirondack chairs arranged around a stone fire pit.

8. The Cove at Yarmouth by Westgate Resorts

West Yarmouth

Manizheh

￥16,447 total

includes taxes & fees

Nov 17 - Nov 18

A wooden deck with a fire pit, outdoor seating, and a pool area at dusk.

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

Brewster

Jack N.

￥108,995 total

includes taxes & fees

Nov 25 - Nov 26

A beach with clear skies and calm waters.

10. Seaside Getaway - Harwichport Beachhouse

Harwich

Meredith R.

￥69,775 total

includes taxes & fees

Nov 18 - Nov 19

A bedroom with a bed, a desk, a chair, a TV, and a window.

11. Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays

Harwich

Nicole M.

￥57,310 total

includes taxes & fees

Nov 16 - Nov 17

A beach with a rocky shoreline and calm waves.

12. 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

￥99,291 total

includes taxes & fees

Dec 13 - Dec 14

A sandy beach path leading to the ocean with a clear sky.

13. Beach Walks, Books & Bay Sunsets

Brewster

Sandra G.

￥83,628 total

includes taxes & fees

Nov 17 - Nov 18

A modern kitchen with white cabinets, a granite island, stainless steel appliances, and pendant lighting.

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

West Brewster

Jim M.

￥116,974 total

includes taxes & fees

Nov 13 - Nov 14

A two-story house with a grey exterior and white trim, surrounded by a well-maintained garden with various plants and flowers.

15. 2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.

Eastham

Mark T R.

￥152,863 total

includes taxes & fees

Nov 13 - Nov 14

A wicker hanging chair with a metal frame, a small round table with a glass, and a bottle, set on a gravel path with a view of a body of water and greenery.

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

EASTHAM

Myriam A.

￥76,560 total

includes taxes & fees

Nov 15 - Nov 16

A house with a white porch, a door, and a garden with flowers and greenery.

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

Eastham

Nancy S.

￥74,461 total

includes taxes & fees

Nov 16 - Nov 17

A residential street with houses, a fire hydrant, and a clear blue sky.

18. Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC

Harwich

david r.

￥88,829 total

includes taxes & fees

Nov 18 - Nov 19

A two-story house with a covered porch, a lawn, and a pathway leading to the entrance.

19. Beach Bungalow: Steps to Beach, Luxury Family Fun

Harwich

Christopher R.

￥93,282 total

includes taxes & fees

Nov 16 - Nov 17

A row of white buildings with storefronts, including a visible sign for 'Chatham' and a 'Chatham' sign above a window.

20. Lovely House 5 Min to Beach with Deck, Grill, Garage

Eastham

Susan C.

￥72,974 total

includes taxes & fees

Nov 15 - Nov 16

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Find vacation rentals that suit your style

Top Chatham Hotel Reviews

A room with a bed, two wicker chairs, a small table, a coffee maker, and a view of the sea through a window.

Chatham Tides

South Chatham

10/10 Excellent

joanna

A pathway leading to a beach with boats in the background and a building with a tower.

Chatham Bars Inn

Chatham

10/10 Excellent

Highly recommend Chatham Bars Inn! Stay in the cottages along the water and start each day with a view of the sunrise, fishing boats, and harbor seals. Walk to the pool, beach, and the buffet breakfast. Walk to Main Street in town for even more restaurants, ice cream and candy shops, and great browsing in stores you can only find on the Cape. Staff was excellent and very professional. Everyone - check-in staff, pool and beach staff, restaurant staff, kids camp staff, were extremely...

Marc

A house with a view of a lake, outdoor seating, and a dock.

Wequassett Resort and Golf Club

Harwich

10/10 Excellent

ruby12376

A flagpole with an American flag, a circular flower bed with pink and white flowers, and white Adirondack chairs.

A Beach Breeze Inn

West Harwich

10/10 Excellent

Lois

A two-story house with a symmetrical facade, a central entrance, and a flag.

Candleberry Inn on Cape Cod

Brewster

10/10 Excellent

Great place to stay! My husband and I were a little worried about vacationing during the pandemic. But, we were put at ease when we read about the policies the innkeepers (Marco and Angelo) put in place during COVID-19, and the overall cleanliness of the inn and our room. The gourmet breakfast and afternoon treats were delicious! It's one of the things we look forward each day. The amenities were great! Since a lot of the restaurants are already fully booked, we're fortunate to have our own...

Maria&Mike

A two-story house with a covered porch, a brick pathway leading to the entrance, and a well-maintained lawn.

Charm on Main by Ocean Edge

Sea Pines

10/10 Excellent

Laura

Skaket Beach Motel

Orleans

10/10 Excellent

Dolores

A hotel with a white facade, a covered outdoor seating area with white chairs and tables, and a view of the sunset.

The Escape Inn

Bass River

10/10 Excellent

Steven

A restaurant with brick arches, wooden tables, and chairs. There is a bar area with bottles and a television screen.

The Villages at Ocean Edge

Brewster

10/10 Excellent

Amanda

A man sitting at a table with a laptop, overlooking a pool area with chairs and tables.

Hyannis Travel Inn

Hyannis

10/10 Excellent

The location is everything as it is 1 street over from main street. The room was a nice size with 2 double beds and was clean with a large private balcony overlooking the street. The room had a mini fridge, a TV with limited cable, a telephone, great air conditioning and lighting. The bathroom was small with a very small and low toilet, low water pressure and a very small shower head, but the water temperature was good. Also limited counter space. The beds were very uncomfortable , uneven And...

Luis

A two-story house with a balcony, a chimney, and a garden with a white archway.

An English Garden Bed & Breakfast

Dennis Port

10/10 Excellent

Frank

A pool area with a wooden deck, metal chairs, and lush greenery.

Brewster by the Sea Inn

West Brewster

10/10 Excellent

Tony and Rachel

A window with a view of the beach and ocean.

Nauset Beach Inn

East Orleans

10/10 Excellent

The Nauset Beach Inn at Orleans is a special gem. The accommodations were clean and well kept. The view from our living room picture window was amazing, especial the early morning sunrises. Glorious! Not to be missed. We enjoyed the large firepit afternoons and evenings. The fireplace was a nice touch. Location was convenient for the many places to eat and visit. The owner was friendly and helpful. One suggestion for our cabin #4 is that it needs a shelf for toiletries in the bathroom. There...

RICHARD

A modern two-story house with a large balcony, a well-maintained lawn, and a view of the water at sunset.

Pelham House Resort

Dennis Port

10/10 Excellent

Anonymous traveler

Blue Lobster Inn

Bass River

10/10 Excellent

Crystal

A large, red-roofed building with a stone facade, surrounded by well-maintained gardens and a cobblestone driveway.

The Mansion at Ocean Edge

Brewster

10/10 Excellent

This is a beautiful resort with an astonishing private beach. The rooms are big and beautiful with a comfortable bed and a great bathroom and shower. The people who work at the resort are attentive and friendly and provide top notch customer service. Upon entering your room,you are welcomed with your name on the TV, classical music, and a complimentary basket of fruit and Voss water. This will be my only choice from now on when staying in Cape Cod. We loved it. A class act. And a fantastic...

Crystal & Rick

Find out more about Chatham

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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.

Chatham Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chatham vacation rentals

1. Beautiful home near Jacknife Beach and bike trail

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

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

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

5. Family Cottage Close to Beach!!

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

7. The Captain's Quarters Suite Unit - 10

8. The Cove at Yarmouth by Westgate Resorts

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

10. Seaside Getaway - Harwichport Beachhouse

11. Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays

12. The Brewster Pearl

13. Beach Walks, Books & Bay Sunsets

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

15. 2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.

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

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

18. Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC

19. Beach Bungalow: Steps to Beach, Luxury Family Fun

20. Lovely House 5 Min to Beach with Deck, Grill, Garage

Find vacation rentals that suit your style

Top Chatham Hotel Reviews

Chatham Tides

10/10 Excellent

Find out more about Chatham

Frequently Asked Questions

Can I find a vacation rental in Chatham?

What are some of the best vacation rentals that Chatham has to offer?

How many vacation rentals are there in Chatham?

What can I see and do in Chatham?

What are vacation rentals like in Chatham?