Chatham Vacation Homes

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

Erin M.

HK$4,710 total

includes taxes & fees

29 Sept - 30 Sept

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.

HK$5,286 total

includes taxes & fees

30 Sept - 1 Oct

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

3. Beautiful home near Jacknife Beach and bike trail

Chatham

Barbara P.

HK$6,054 total

includes taxes & fees

9 Sept - 10 Sept

A kitchen with white cabinets, a dining table with chairs, a grill outside, and a view of trees through the window.

4. Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard

Chatham

Will M.

HK$4,850 total

includes taxes & fees

10 Sept - 11 Sept

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.

HK$13,403 total

includes taxes & fees

21 Sept - 22 Sept

A covered deck with a grill, outdoor furniture, and a view of trees.

6. Great for Families! Brewster Home 6 Mi to Beach

Brewster

Stacey P.

HK$5,537 total

includes taxes & fees

20 Sept - 21 Sept

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

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

Harwich

Ashley M.

HK$4,012 total

includes taxes & fees

28 Sept - 29 Sept

A living room with a fireplace, sofas, a TV, and a bookshelf.

8. Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

West Brewster

Gregg H.

HK$5,177 total

includes taxes & fees

8 Sept - 9 Sept

A covered porch with white railings and blue shutters, featuring two rocking chairs and a hanging flower basket.

9. New! 4BR Fire Pit, Ping Pong, Movie Room

Harwich

Matt M.

HK$7,231 total

includes taxes & fees

3 Sept - 4 Sept

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

10. Family Cottage Close to Beach!!

Harwichport

John N.

HK$6,406 total

includes taxes & fees

14 Sept - 15 Sept

A two-story house with a stone staircase leading to the front door, surrounded by a well-maintained lawn and trees.

11. New! Chatham Cottage- 1 Mile to Downtown & Beaches

Chatham

Deanna M.

HK$6,808 total

includes taxes & fees

26 Sept - 27 Sept

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

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

HK$5,743 total

includes taxes & fees

29 Sept - 30 Sept

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

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

Dennis

Patrick T.

HK$2,827 total

includes taxes & fees

27 Sept - 28 Sept

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

14. Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

Harwich

Norman Y.

HK$6,459 total

includes taxes & fees

8 Sept - 9 Sept

A lake surrounded by dense trees, viewed from a wooden deck.

15. Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!

Chatham

Anonymous traveller

A coastal scene with a lighthouse, beach, and ocean.

16. Beach Chic Chatham 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC

Chatham

Amanda B.

HK$10,571 total

includes taxes & fees

7 Sept - 8 Sept

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

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

Dennis Port

Carol S.

HK$3,484 total

includes taxes & fees

1 Oct - 2 Oct

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

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

Eastham

Susan C.

HK$3,960 total

includes taxes & fees

28 Sept - 29 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.

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

West Brewster

Reba W.

HK$7,170 total

includes taxes & fees

28 Sept - 29 Sept

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

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

Harwich

HK$5,591 total

includes taxes & fees

20 Sept - 21 Sept

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Top Chatham Hotel Reviews

Queen Anne Inn

8/10 Good

"So the property is closing after Labor Day for a full remodel and showed every day of its use. Although noted in their notice, I did not catch it and thought that it was a different property that we stayed at previously. My bad"

Hyannis Harbor Hotel

10/10 Excellent

"We love this hotel. We came to the cape every 1-2 years and we always stay at this hotel. The staff is friendly, you can’t beat the location, the pool and spa is great. The rooms are perfect! Our room was missing a screen door for the slider so we weren’t able to keep the sliding door open as often as we would have hoped but it was still a great time!"

Pleasant Bay Village Resort

10/10 Excellent

"A wonderful place to stay in Chatham. Literally a five minute drive to the pier fish market, Main Street and the beach. Check in was easy and the staff person was very helpful in pointing out places to eat and places to go both in Chatham and nearby Orleans. The room was very clean, spacious and the turn down service was excellent. They have a great pool and hot tub. They also have a koi fish pond that is beautiful. We especially enjoyed the outdoor tables in the courtyards of each area. We were able to bring back lobster rolls from the fish market and enjoy a nice al fresco dinner. We then ran into the cleaning who offered to take our garbage from us, which was so helpful as it prevented us from stinking up the room. I would definitely recommend this resort to anyone staying n Chatham. Well worth it!"

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