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

Holiday Homes in Chatham

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Chatham holiday homes

TV, fireplace

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

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Chatham
9.6 out of 10, Exceptional, (105 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is NZ$991
includes taxes & fees
31 Aug - 1 Sept
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Dining

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

Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard
Chatham
10.0 out of 10, Exceptional, (108 reviews)
"Great stay. House is in a great location and is well maintained. Bonnie was super helpful. "
United States
Will M.
The price is NZ$1,034
includes taxes & fees
1 Sept - 2 Sept
Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard
Exterior

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

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Chatham
10.0 out of 10, Exceptional, (127 reviews)
"Our stay was wonderful!"
United States
Corinne J.
The price is NZ$1,093
includes taxes & fees
29 Sept - 30 Sept
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Sun-loungers, beach towels

4. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, Exceptional, (86 reviews)
"This is second time to stay here! We love the location and hospitality of the hosts! Great place!"
United States
Barbara P.
The price is NZ$1,283
includes taxes & fees
9 Sept - 10 Sept
Beautiful home near Jacknife Beach and bike trail
Property grounds

5. Spacious 4BR house in perfect Chatham with AC

Spacious 4BR house in perfect Chatham with AC
Chatham
The price is NZ$2,055
includes taxes & fees
13 Sept - 14 Sept
Spacious 4BR house in perfect Chatham with AC
Exterior

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

Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Chatham
10.0 out of 10, Exceptional, (21 reviews)
"House was wonderful with plenty of room. Great outdoor spaces with a deck and patio. Very convenient location. Host responsive to our needs. Would definitely stay again. "
United States
Sally S.
The price is NZ$4,596
includes taxes & fees
17 Sept - 18 Sept
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Outdoor dining

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

Great for Families! Brewster Home 6 Mi to Beach
Brewster
10.0 out of 10, Exceptional, (11 reviews)
"The kitchen was well stocked. The Beds were comfortable. "
United States
Stacey P.
The price is NZ$1,169
includes taxes & fees
1 Sept - 2 Sept
Great for Families! Brewster Home 6 Mi to Beach
Pool

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

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
9.8 out of 10, Exceptional, (14 reviews)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is NZ$827
includes taxes & fees
28 Sept - 29 Sept
Cozy Large Home in Harwich with Patio near Wequassett Resort
Exterior

9. Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (81 reviews)
"Everything was exactly as described - they provided beach towels and chairs which we used - the property was perfect for our stay"
United States
John N.
The price is NZ$1,315
includes taxes & fees
6 Sept - 7 Sept
Family Cottage Close to Beach!!
Exterior

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

New! Chatham Cottage- 1 Mile to Downtown & Beaches
Chatham
9.8 out of 10, Exceptional, (11 reviews)
"Close to tpwn beach very clean great for us and pups sweet lplace"
United States
Deanna M.
New! Chatham Cottage- 1 Mile to Downtown & Beaches
Terrace/patio

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

New! 4BR Fire Pit, Ping Pong, Movie Room
Harwich
10.0 out of 10, Exceptional, (2 reviews)
"Very responsive and friendly host. "
United States
Matt M.
New! 4BR Fire Pit, Ping Pong, Movie Room
TV, offices

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

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, Exceptional, (51 reviews)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is NZ$1,168
includes taxes & fees
8 Sept - 9 Sept
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
TV, DVD player, offices

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

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Dennis Port
9.0 out of 10, Wonderful, (26 reviews)
"Loved this property. "
United States
Carol S.
The price is NZ$813
includes taxes & fees
1 Sept - 2 Sept
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Outdoor dining

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

Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
Harwich
10.0 out of 10, Exceptional, (8 reviews)
"Excellent location "
United States
Norman Y.
The price is NZ$1,430
includes taxes & fees
8 Sept - 9 Sept
Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
Sun-loungers, beach towels

15. The Brewster Pearl

The Brewster Pearl
Brewster
10.0 out of 10, Exceptional, (2 reviews)
"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...
United States
PAULA
The price is NZ$1,293
includes taxes & fees
27 Sept - 28 Sept
The Brewster Pearl
Beach nearby, sun-loungers, beach umbrellas, beach towels

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

Beach Chic Chatham 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC
Chatham
10.0 out of 10, Exceptional, (88 reviews)
"We had an incredible time staying in this home! The place was beautiful and the location was very convenient/ central to everything. The host was also super responsive and gave great recommendations! We will definitely be booking again in the future"
United States
Kaitlyn P.
The price is NZ$2,163
includes taxes & fees
7 Sept - 8 Sept
Beach Chic Chatham 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC
Dining

17. Cape Cod's "Beach Rose"

Cape Cod's "Beach Rose"
Dennis
10.0 out of 10, Exceptional, (29 reviews)
"Very clean, great place for kids!"
United States
Ruth
The price is NZ$376
includes taxes & fees
9 Sept - 10 Sept
Cape Cod's "Beach Rose"
Property grounds

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

Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!
Chatham
10.0 out of 10, Exceptional, (33 reviews)
"The location of the house is great. We loved the view of the water we got to enjoy every day. Plus it’s just a short drive from Main Street in South Chatham, the Nantucket ferry on Harwich, and sunsets on Skaket beach or Rock Harbor. We enjoyed the fire pit and boating on the lake too. Perfect spot for a family."
United States
Anonymous traveller
The price is NZ$2,041
includes taxes & fees
12 Sept - 13 Sept
Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!
Outdoor dining

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

Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
Dennis Port
4.0 out of 10, (1 review)
"Excellent vacation in a great spot but the property needs some care."
United States
Art E.
The price is NZ$788
includes taxes & fees
2 Sept - 3 Sept
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
2 bedrooms, desk, iron/ironing board, WiFi

20. Cape Calm: A Harwich Port Coastal Haven

Cape Calm: A Harwich Port Coastal Haven
Harwich
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place close to town and lots of beaches"
United States
Lee C.
The price is NZ$1,130
includes taxes & fees
21 Sept - 22 Sept
Cape Calm: A Harwich Port Coastal Haven
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chatham Hotel Reviews

Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

8/10 Good
"Rooms were kept very neat and clean, WiFi was very spotty."
Ruth 5-night trip
Posted 3 hours ago
Uncommoner Hotel by Reverie Boutique Collection

Find out more about Chatham

Chatham Holiday Homes information

Number of reviews
710
Accommodation
2541 Holiday Homes
Lowest Price
NZ$376
Highest Price
NZ$4,596