Chatham Vacation Rentals from CA $124: Short-Term Rentals for 2026

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Our top choices for Chatham vacation rentals

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

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

Chatham

Jennifer B.

CA $757 total

includes taxes & fees

Nov 9 - Nov 10

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

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

Chatham

Corinne J.

CA $776 total

includes taxes & fees

Nov 9 - Nov 10

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

3. Beautiful home near Jacknife Beach and bike trail

Chatham

Claire D.

CA $817 total

includes taxes & fees

Nov 9 - Nov 10

A two-story house with a covered porch and a stone staircase leading to the entrance.

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

Chatham

Sally S.

A beach with people, tents, and umbrellas.

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

Brewster

Rebecca R.

CA $442 total

includes taxes & fees

Nov 9 - Nov 10

An outdoor dining area with white chairs and umbrellas, overlooking the ocean.

6. 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Dennis

Betsy D.

CA $417 total

includes taxes & fees

Nov 8 - Nov 9

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

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

Harwich

Norman Y.

CA $780 total

includes taxes & fees

Nov 9 - Nov 10

A pool area with lounge chairs and flags.

8. The Cove at Yarmouth by Westgate Resorts

West Yarmouth

Kim

CA $172 total

includes taxes & fees

Nov 11 - Nov 12

A beach with footprints, a large rock, and a clear sky.

9. 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

CA $828 total

includes taxes & fees

Nov 10 - Nov 11

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

10. Family Cottage Close to Beach!!

Harwichport

"From check-in to check-out, our experience was excellent. There were minor issues with the house, that didn’t affect our stay. It’s a quiet neighborhood, and we all slept well. The Internet was fast enough for my son’s gaming laptop (spent indoors on a rainy day). There are two outdoor grills available. I used the charcoal grill, as I prefer the flavoring from the burner charcoal. In the yard, you’ll see a wide assortment of birds. Everyday we had a visit by rabbits and chipmunks. Nearby,...

Gil G.

CA $1,035 total

includes taxes & fees

Nov 9 - Nov 10

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

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

EASTHAM

Myriam A.

CA $669 total

includes taxes & fees

Nov 16 - Nov 17

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

Nicole M.

CA $485 total

includes taxes & fees

Nov 9 - Nov 10

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!

West Brewster

Jim M.

CA $1,028 total

includes taxes & fees

Nov 8 - Nov 9

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

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

Eastham

Nancy S.

CA $677 total

includes taxes & fees

Nov 16 - Nov 17

A beach with a wooden walkway leading to the shore, a rocky breakwater, and a clear sky at sunset.

15. Seaside Getaway - Harwichport Beachhouse

Harwich

Meredith R.

CA $590 total

includes taxes & fees

Nov 9 - Nov 10

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

16. Beach Walks, Books & Bay Sunsets

Brewster

Sandra G.

CA $762 total

includes taxes & fees

Nov 9 - Nov 10

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

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

Dennis Port

Art E.

CA $686 total

includes taxes & fees

Nov 9 - Nov 10

A table set outdoors with a view of a lake, surrounded by trees.

18. 🦀Waterfront at The Velvet Crab~Amazing Sunsets

Eastham

Emily A.

CA $582 total

includes taxes & fees

Nov 16 - Nov 17

A spacious living area with wooden floors, a large dining table, and multiple windows offering a view of the beach.

19. 10 min walk to Beach - Home with Amazing View & Huge Deck

Eastham

Sabrina H.

CA $727 total

includes taxes & fees

Nov 18 - Nov 19

Two Adirondack chairs facing a calm lake with a forested shoreline under a partly cloudy sky.

20. The Breeze on Minister's Pond

Eastham

MelanieC

CA $557 total

includes taxes & fees

Nov 16 - Nov 17

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Top Chatham Hotel Reviews

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

Candleberry Inn on Cape Cod

Brewster

10/10 Excellent

Anonymous traveller

A swimming pool with a fountain, surrounded by greenery and a gazebo.

Brewster by the Sea Inn

West Brewster

10/10 Excellent

We spent a full week at Brewster by the Sea Inn in early September and can't say enough good things about our time there. Amy is a wonderful and warm hostess, with so many great reccos for things to see and do on the Cape. Our room was spacious, comfortable, clean and quiet. The breakfasts were delicious and we loved being able to sit outside on the deck every morning and be served by the polite, attentive and accommodating staff. Having our morning visit with Sweet Pea, the friendly resident...

Allison

A white building with a sign reading "The Village Inn" indicating it is a fine lodging and breakfast establishment.

The Village Inn Cape Cod

Yarmouth Port

10/10 Excellent

Francine

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

Spent a fantastic two nights at the Beach Breeze Inn. The room was extremely clean and spacious and the pool area was very well kept. The owners were incredibly kind and offered plenty of suggestions for site seeing around Cape Cod. Beach towels and chairs were available to borrow for off-site adventures, which was a very pleasant surprise. The location was perfect, with a very short drive to Harwich for shopping and eating and the drive to Hyannis was very easy. We will definitely be back!...

Mackenzie

A large, two-story house with a well-maintained lawn and a prominent tree in front.

The Old Manse Inn

Brewster

10/10 Excellent

Marilou

A porch with white chairs and a planter with flowers.

The Captain Farris House B&B

Bass River

10/10 Excellent

Beth

Blue Lobster Inn

Bass River

10/10 Excellent

Mario

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 reviews are true, this is a great place to stay. We based ourselves here as we explored the Cape. It’s a 10 minute walk to the port where you catch the ferries to Nantucket and the Vineyard. Main st Hyannis is the next street over. You really can’t beat the location. The staff is friendly and extremely helpful. The breakfast was good and there was always plenty. The rooms are very basic, nothing fancy at all, no bells and whistles. Just a basic room with all the necessities for a decent...

Cristina

An outdoor patio area with wicker furniture, a round table with a fire pit, and a white chair.

The Inn at Yarmouth Port

Yarmouth Port

10/10 Excellent

My wife and I were fortunate enough to spend a full week at this beautiful Inn. Our hosts, Kathleen and Chuck (as well as the rest of the staff) went the extra mile to make sure we had the perfect getaway! The freshly made breakfasts every morning were excellent (they served mostly local products), the location was perfect and the grounds were beautiful (loved all the flowers). The rooms were also recently renovated :) if you're searching for a couple's retreat in Cape Cod, look no further!

David Anthony

A pathway flanked by vibrant flowers and greenery, leading to a house with large windows.

The Villa Callo Inn

West Harwich

10/10 Excellent

Domenico

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, 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 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chatham vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chatham vacation rentals we have selected for you start as low as CA $124 per night. Entering your travel dates in the search wizard 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.

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.

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Chatham Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chatham vacation rentals

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

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

3. Beautiful home near Jacknife Beach and bike trail

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

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

6. 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

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

8. The Cove at Yarmouth by Westgate Resorts

9. The Brewster Pearl

10. Family Cottage Close to Beach!!

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

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

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

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

15. Seaside Getaway - Harwichport Beachhouse

16. Beach Walks, Books & Bay Sunsets

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

18. 🦀Waterfront at The Velvet Crab~Amazing Sunsets

19. 10 min walk to Beach - Home with Amazing View & Huge Deck

20. The Breeze on Minister's Pond

Find vacation rentals that suit your style

Top Chatham Hotel Reviews

Candleberry Inn on Cape Cod

10/10 Excellent

Find out more about Chatham

Chatham vacation rentals: An excellent choice for every season

How to find incredible deals on Chatham rentals

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?

Explore a world of travel with Expedia