Chatham Holiday Homes from £177: Search Holiday Homes in Chatham

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

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Our top choices for Chatham holiday homes

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

Mark K.

includes taxes & fees

12 Oct - 13 Oct

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

Joanne B.

includes taxes & fees

4 Oct - 5 Oct

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

3. Beautiful home near Jacknife Beach and bike trail

Chatham

Barbara P.

includes taxes & fees

29 Sept - 30 Sept

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.

includes taxes & fees

25 Oct - 26 Oct

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

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

Harwich

Bill F.

includes taxes & fees

29 Sept - 30 Sept

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

6. Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

Harwich

Norman Y.

includes taxes & fees

29 Sept - 30 Sept

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.

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

West Brewster

Jim M.

includes taxes & fees

2 Oct - 3 Oct

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

8. Family Cottage Close to Beach!!

Harwichport

John N.

includes taxes & fees

29 Sept - 30 Sept

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

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

Dennis Port

Art E.

includes taxes & fees

1 Oct - 2 Oct

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

10. 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

27 Oct - 28 Oct

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

11. 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Dennis

Patrick T.

includes taxes & fees

14 Oct - 15 Oct

A wooden-paneled room with a sofa, chairs, a table, a fireplace, and a clock.

12. Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Dennis Port

Laurie and Rick A.

includes taxes & fees

5 Oct - 6 Oct

A kitchen with white cabinetry, a granite countertop, an outdoor patio with a table and chairs, and a view of a house with a tree.

13. Cape Cod Cottage Near Beaches & Bike Trail

Harwich

"We absolutely LOVED this home. We have stayed in condo style prior each year, and we loved the space, inside and outside, of this quintessential Cape Cod home and neighborhood. It has been updated with appliances and home decor which made it comfortable for all. It is a pet friendly home, as we had a dog with us- and we didn’t walk in to anything different than a non pet friendly home. I will request to rent this home again and again and recommend it highly. The owners were very communicative...

Holly c.

includes taxes & fees

29 Sept - 30 Sept

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

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

Harwich

includes taxes & fees

4 Oct - 5 Oct

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

15. Beach Walks, Books & Bay Sunsets

Brewster

Sandra G.

includes taxes & fees

30 Sept - 1 Oct

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

16. 10 min walk to Beach - Home with Amazing View & Huge Deck

Eastham

includes taxes & fees

29 Sept - 30 Sept

17. Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Eastham

Donna R.

includes taxes & fees

29 Sept - 30 Sept

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

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

Eastham

Anna P.

includes taxes & fees

5 Oct - 6 Oct

A spacious living area with a sofa, chairs, a fireplace, and a kitchen in the background.

19. Lovely 3-bedroom house in Dennis perfect for a relaxing getaway

Dennis

includes taxes & fees

29 Sept - 30 Sept

A kitchen with wooden cabinets, a dining table with chairs, and a kitchen island with baskets.

20. Cape Cod's "Beach Rose"

Dennis

Rachael M.

includes taxes & fees

5 Oct - 6 Oct

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Top Chatham Hotel Reviews

Cape Sands Inn

8/10 Good

"Clean rooms, nothing special hardly anyone there, felt wecould.have better rooms, so.e roo.s had a nice sitting.area in the back by the river. Those are the rooms you want."

Lighthouse Inn

10/10 Excellent

"Property was absolutely breathtaking. The restaurant/bar was steps from the beach and had a beautiful interior. The accommodations were very quaint. It was like stepping back in time. They were clean and comfortable and also allowed for a beautiful view. We were there in off season so it was not busy. I would definitely stay here again."

Chatham Wayside Inn

10/10 Excellent

"Loved the Inn and will definitely stay there again in the future. Perfect location...just steps to the shops and eateries on Main Street. Our standard king room was lovely and spacious. The mattress and bedding was extremely comfortable and had everything we needed. The gym and pool looked beautiful but unfortunately we didn't have a chance to use them. Dinner our first night at the tavern on the property was excellent. The seafood pot pie was absolutely! The only slight downside for us was that the continental breakfast was a bit lacking. Considering the price of the rooms, I think the Inn could do a little better. However, this would not keep us from staying here again. A great experience overall."

Greyfinch Chatham Inn

10/10 Excellent

"This place is so cute! When we first pulled up we were unsure because it looks like an old roadside motel. But it’s quickly apparent that it’s been beautifully updated with fresh paint and hanging plants. The driveway and parking lot are spotless as are the rooms. The decor in the rooms is updated and coastal. The staff was lovely. I would absolutely stay here again!"

Find out more about Chatham

Chatham Holiday Homes information

Number of reviews	704
Accommodation	2541 Holiday Homes
Lowest Price	£177
Highest Price	£1,189

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chatham holiday homes

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. Cozy Large Home in Harwich with Patio near Wequassett Resort

6. Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

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

8. Family Cottage Close to Beach!!

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

10. The Brewster Pearl

11. 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

12. Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

13. Cape Cod Cottage Near Beaches & Bike Trail

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

15. Beach Walks, Books & Bay Sunsets

16. 10 min walk to Beach - Home with Amazing View & Huge Deck

17. Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

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

19. Lovely 3-bedroom house in Dennis perfect for a relaxing getaway

20. Cape Cod's "Beach Rose"

Find holiday rentals that suit your style

Top Chatham Hotel Reviews

Cape Sands Inn

Lighthouse Inn

Chatham Seafarer Inn

Hyannis Travel Inn

The Villages at Ocean Edge

Riviera Beach Resort

Pleasant Bay Village Resort

Chatham Wayside Inn

Greyfinch Chatham Inn

Find out more about Chatham

Chatham Holiday Homes information

Explore a world of travel with Expedia