Chatham Holiday Rentals from NZ$219: Search Short-Term Rentals

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Our top choices for Chatham holiday 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.

includes taxes & fees

1 Dec - 2 Dec

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.

includes taxes & fees

12 Nov - 13 Nov

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

3. Beautiful home near Jacknife Beach and bike trail

Chatham

Claire D.

includes taxes & fees

6 Nov - 7 Nov

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.

includes taxes & fees

8 Nov - 9 Nov

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.

includes taxes & fees

7 Nov - 8 Nov

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.

includes taxes & fees

9 Nov - 10 Nov

A pool area with lounge chairs and flags.

8. The Cove at Yarmouth by Westgate Resorts

West Yarmouth

Kim

includes taxes & fees

9 Nov - 10 Nov

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

includes taxes & fees

10 Nov - 11 Nov

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.

includes taxes & fees

6 Nov - 7 Nov

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.

includes taxes & fees

6 Dec - 7 Dec

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.

includes taxes & fees

17 Nov - 18 Nov

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.

includes taxes & fees

7 Nov - 8 Nov

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.

includes taxes & fees

11 Nov - 12 Nov

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.

includes taxes & fees

9 Nov - 10 Nov

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

16. Beach Walks, Books & Bay Sunsets

Brewster

Sandra G.

includes taxes & fees

19 Nov - 20 Nov

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.

includes taxes & fees

6 Nov - 7 Nov

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

18. 🦀Waterfront at The Velvet Crab~Amazing Sunsets

Eastham

Emily A.

includes taxes & fees

9 Nov - 10 Nov

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.

includes taxes & fees

18 Nov - 19 Nov

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

includes taxes & fees

9 Nov - 10 Nov

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Top Chatham Hotel Reviews

Margaritaville Resort Cape Cod

10/10 Excellent

"Clean, quiet, good location"

Chatham Wayside Inn

8/10 Good

"You can't beat the location, right on Main St. in downtown Chatham - easy walking to lots of shops and restaurants, and the charming public library. The room was very clean, and equipped with a mini-fridge and coffeemaker. We had two queens and the beds were comfortable, with good quality linens. Where we had problems: 1) there were two electrical outlets next to the sink in the bathroom, and all the rest were buried behind beds, the dresser, or other furniture (NOT practical with electronic devices to charge every day; a couple of charging hubs within easy reach would be very helpful); 2) there was no desk or straight chair in this huge room, so when we had work to do, we had to move a tiny side table in front of a large armchair to get anything done; 3) the louvred wooden blinds are not room-darkening, so the light WILL wake you when the sun comes up. Finally, a run-down on the continental breakfast: on 10-30-2026 the breakfast included bagels (w.cream cheese available), small scones, some muffins, cold cereal and whole milk, fresh cut-up fruit like honeydew and strawberries, whole apples and pears, yogurt cups, a warming pan of scrambled eggs, plus coffee, tea, and orange juice. Pretty generous for a "continental" breakfast! Our only recommendation there would be to add oatmeal, or at least make instant oatmeal packets available for those of us who need a healthier option that does not involve milk. Overall a decent option if you don't need to work during your stay."

Find out more about Chatham

Everything you need to know about Chatham holiday rentals

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

Chatham holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chatham holiday rentals we have selected for you start as low as NZ$219 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 holiday 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 holiday.

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 holiday rental in Chatham?

Yes, there are holiday rentals in Chatham close to Chatham Railroad Museum, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Chatham has to offer?

Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!: This holiday home rental outside of Chatham is located on the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade/games room.

How many holiday rentals are there in Chatham?

With 277 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Chatham?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chatham. Holiday rentals offer extras such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.

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Check prices for these dates

Our top choices for Chatham holiday 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 holiday rentals that suit your style

Top Chatham Hotel Reviews

Margaritaville Resort Cape Cod

Uncommoner Hotel by Reverie Boutique Collection

Sunbird Cape Cod Resort

Old Harbor Inn

Cape Sands Inn

Chatham Wayside Inn

Chatham Bars Inn

Greyfinch Chatham Inn

The Hawthorne

Find out more about Chatham

Frequently asked questions

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