Chatham, MA Vacation Homes from AED 843

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 vacation homes

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

Chatham

Erin M.

AED 2,212 total

includes taxes & fees

29 Sep - 30 Sep

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

Chatham

Corinne J.

AED 2,476 total

includes taxes & fees

29 Sep - 30 Sep

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

Chatham

Will M.

AED 2,272 total

includes taxes & fees

10 Sep - 11 Sep

4. Beautiful home near Jacknife Beach and bike trail

Chatham

Barbara P.

AED 2,644 total

includes taxes & fees

1 Oct - 2 Oct

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

Chatham

Sally S.

AED 6,279 total

includes taxes & fees

21 Sep - 22 Sep

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

Brewster

Stacey P.

AED 2,594 total

includes taxes & fees

20 Sep - 21 Sep

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

Harwich

Ashley M.

AED 1,880 total

includes taxes & fees

28 Sep - 29 Sep

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

Harwich

Matt M.

AED 3,473 total

includes taxes & fees

3 Sep - 4 Sep

9. Family Cottage Close to Beach!!

Harwichport

John N.

AED 2,972 total

includes taxes & fees

6 Sep - 7 Sep

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

West Brewster

Gregg H.

AED 2,562 total

includes taxes & fees

8 Sep - 9 Sep

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

Dennis

Patrick T.

AED 1,324 total

includes taxes & fees

27 Sep - 28 Sep

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

Harwich

Norman Y.

AED 3,170 total

includes taxes & fees

8 Sep - 9 Sep

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

Chatham

Anonymous traveler

14. 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

15. Cape Cod's "Beach Rose"

Dennis

Ruth

AED 843 total

includes taxes & fees

9 Sep - 10 Sep

Beach nearby, sun loungers, beach umbrellas, beach towels

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

Chatham

Amanda B.

AED 4,927 total

includes taxes & fees

7 Sep - 8 Sep

17. The Genoa | Your Perfect Dennis Port Beach Escape

Dennis Port

Anonymous traveler

AED 1,935 total

includes taxes & fees

2 Sep - 3 Sep

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

Dennis Port

Carol S.

AED 1,722 total

includes taxes & fees

1 Oct - 2 Oct

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

Eastham

Susan C.

AED 1,855 total

includes taxes & fees

28 Sep - 29 Sep

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

West Brewster

Reba W.

AED 3,359 total

includes taxes & fees

28 Sep - 29 Sep

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Top Chatham Hotel Reviews

The Villages at Ocean Edge

10/10 Excellent

"Okokokok"

Lighthouse Inn

10/10 Excellent

"Excellent location! You’re right on the beach and right next to West Dennis beach for long walks. Lots of activities available for kids & adults. Enjoyed the Meridian Restaurant. Ate there multiple times and both my husband and I had a very good meal every time. I marveled at the amount of help they have to make things run smoothly. Based on some of the reviews I had read, this apparently had been problematic initially but certainly isn’t the case now. All staff were delightful to deal with."

Queen Anne Inn

8/10 Good

"7/10 — Charming property with room for improvement We stayed for two nights this past weekend and overall had a pleasant stay. We were in the back cottage, and the room itself was totally fine. I especially liked the hardwood floors, and we had no major concerns with the room during our stay. The bathroom could use some updating, but everything was functional. The main building has a cute, eclectic New England feel, with some really charming sitting areas and common spaces. There’s definitely a lot of character to the property, and with a few updates and a little more attention to the grounds, I think it could be a really lovely place. One area that stood out was the upkeep of the outdoor spaces. There were tables and chairs with quite a few fallen leaves sitting on them throughout the weekend, which made the outdoor areas feel a bit less inviting than they could have been. A little more regular maintenance would make a noticeable difference. The front desk receptionist was wonderful. She was very friendly and checked in with us a couple of times throughout the weekend to make sure everything was going well and that we didn’t need anything, which we really appreciated. Overall, we had a good stay and everything went smoothly. The property has a lot of charm and potential, and I think some updates to the bathrooms and a bit more attention to the outdoor grounds could really elevate the experience."

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!"

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chatham vacation 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. Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard

4. Beautiful home near Jacknife Beach and bike trail

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

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

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