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

Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chatham vacation 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

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Chatham
9.6 out of 10, Exceptional, (108 reviews)
"Excellent location and stay at the lucky 7 cottage. The communication with the host was outstanding, best I’ve experienced. We’ll definitely be back for another time at this location."
United States
Mark K.
The price is CA $202
CA $796 total
includes taxes & fees
Nov 1 - Nov 2
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
A living room with a white cabinet, striped armchair, and a wicker chair.

2. 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, (128 reviews)
"Our stay was wonderful!"
United States
Corinne J.
The price is CA $315
CA $768 total
includes taxes & fees
Nov 2 - Nov 3
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
A deck with outdoor furniture including a sofa, chairs, and a table.

3. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, Exceptional, (94 reviews)
"Beautiful, clean home with very responsive and kind hosts!"
United States
Claire D.
The price is CA $377
CA $859 total
includes taxes & fees
Nov 1 - Nov 2
Beautiful home near Jacknife Beach and bike trail
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

Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Chatham
10.0 out of 10, Exceptional, (24 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 CA $1,567
CA $2,004 total
includes taxes & fees
Nov 4 - Nov 5
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
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

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
9.8 out of 10, Exceptional, (15 reviews)
"Great host. Convenient location for a visit to Chatham."
United States
Bill F.
Cozy Large Home in Harwich with Patio near Wequassett Resort
An outdoor patio with Adirondack chairs, a fire pit, and string lights.

6. Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard

Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard
Harwich
10.0 out of 10, Exceptional, (11 reviews)
"Excellent location "
United States
Norman Y.
The price is CA $236
CA $858 total
includes taxes & fees
Oct 31 - Nov 1
Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard
A living room with a fireplace, sofas, a coffee table, and a television.

7. 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Dennis
10.0 out of 10, Exceptional, (209 reviews)
"Great location and perfect home for overnight stay!"
United States
Betsy D.
The price is CA $125
CA $437 total
includes taxes & fees
Nov 7 - Nov 8
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
A living room with a fireplace, a sofa, a coffee table, and a television.

8. The Brewster Pearl

The Brewster Pearl
Brewster
10.0 out of 10, Exceptional, (3 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 CA $280
CA $914 total
includes taxes & fees
Nov 1 - Nov 2
The Brewster Pearl
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.

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

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
West Brewster
10.0 out of 10, Exceptional, (38 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is CA $267
CA $1,065 total
includes taxes & fees
Nov 2 - Nov 3
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
A two-story house with a front porch, a chimney, and a well-maintained lawn.

10. Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (83 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 CA $440
CA $1,143 total
includes taxes & fees
Nov 1 - Nov 2
Family Cottage Close to Beach!!
A wooden deck with outdoor furniture, a covered seating area, and a view of neighboring houses.

11. 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 CA $162
CA $692 total
includes taxes & fees
Oct 31 - Nov 1
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
A residential backyard with a white fence, outdoor seating, and a house in the background.

12. Seaside Getaway - Harwichport Beachhouse

Seaside Getaway - Harwichport Beachhouse
Harwich
9.2 out of 10, Wonderful, (19 reviews)
"Great stay! Clean and comfortable and close to town."
United States
Meredith R.
The price is CA $288
CA $651 total
includes taxes & fees
Nov 2 - Nov 3
Seaside Getaway - Harwichport Beachhouse
A wooden deck with a ceiling fan, a sofa, and chairs.

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

Lovely House 5 Min to Beach with Deck, Grill, Garage
Eastham
10.0 out of 10, Exceptional, (4 reviews)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is CA $197
CA $640 total
includes taxes & fees
Nov 1 - Nov 2
Lovely House 5 Min to Beach with Deck, Grill, Garage
A living room with a grey sofa, striped rug, and a lamp.

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

The Pet-Friendly Surf Shack Hideaway on the Cove
Eastham
10.0 out of 10, Exceptional, (30 reviews)
"It was a beautiful house and well stocked with all your needs. Also located in a great area."
United States
Nancy S.
The price is CA $214
CA $711 total
includes taxes & fees
Nov 2 - Nov 3
The Pet-Friendly Surf Shack Hideaway on the Cove
A bedroom with a bed, a desk, a chair, a TV, and a window.

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

Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
Harwich
9.8 out of 10, Exceptional, (8 reviews)
"We loved staying at this beautiful house in Harwich. The property was clean, cozy and felt just like home. There was a fenced in back yard which was perfect for our dog and kids. Very private and close to shops, restaurants and the beach. We look forward to visiting again in the future!"
United States
Nicole M.
The price is CA $346
CA $535 total
includes taxes & fees
Nov 1 - Nov 2
Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
A dining area with a table set for two, a chair, and a plant with pink flowers.

16. Beach Walks, Books & Bay Sunsets

Beach Walks, Books & Bay Sunsets
Brewster
10.0 out of 10, Exceptional, (3 reviews)
"The property was very clean, lots of little excellent touches, and amazing views. We truly enjoyed the pathway to the private beach. I wished we could have stayed longer. We will definitely be booking again."
United States
Sandra G.
The price is CA $262
CA $800 total
includes taxes & fees
Nov 9 - Nov 10
Beach Walks, Books & Bay Sunsets
A modern two-story building with large windows and a flat roof.

17. Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!

Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!
Dennis Port
9.8 out of 10, Exceptional, (17 reviews)
"The property was great and hope to be back in the future."
United States
Jason H.
Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!
A spacious living area with wooden floors, a large dining table, and multiple windows offering a view of the beach.

18. 10 min walk to Beach - Home with Amazing View & Huge Deck

10 min walk to Beach - Home with Amazing View & Huge Deck
Eastham
The price is CA $312
CA $819 total
includes taxes & fees
Nov 18 - Nov 19
10 min walk to Beach - Home with Amazing View & Huge Deck
A room with a wooden piano, a round mirror, a white door leading to a balcony with a view of greenery, and a hanging light fixture.

19. Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
Dennis
10.0 out of 10, Exceptional, (1 review)
"Great location. Spacious house."
United States
Diana S.
The price is CA $224
CA $673 total
includes taxes & fees
Nov 2 - Nov 3
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
A modern kitchen with white cabinets, a wooden ceiling, and a herringbone-patterned floor.

20. Beach Bungalow: Steps to Beach, Luxury Family Fun

Beach Bungalow: Steps to Beach, Luxury Family Fun
Harwich
10.0 out of 10, Exceptional, (10 reviews)
"We had an excellent stay on the cape at this beautiful home that was walking distance to the beach. The location was perfect and neighborhood was exactly what we dreamed of for an offseason getaway."
United States
Christopher R.
The price is CA $294
CA $864 total
includes taxes & fees
Nov 11 - Nov 12
Beach Bungalow: Steps to Beach, Luxury Family Fun
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

Hyannis Harbor Hotel

Hyannis Harbor Hotel

10/10 Excellent
"Great location"
Gary 1-night trip
Posted 1 hour ago
Hyannis Harbor Hotel

Find out more about Chatham

Chatham Vacation Homes information

Number of reviews
779
Accommodation
2435 Vacation Homes
Lowest Price
CA $437
Highest Price
CA $2,004

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