A wooden building with a sloped roof, stone benches, and statues.

Holiday Homes in Brewster

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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 Brewster holiday homes

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

1. 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 AU$939
includes taxes & fees
8 Sept - 9 Sept
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
A covered deck with a grill, outdoor furniture, and a view of trees.

2. 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 AU$944
includes taxes & fees
20 Sept - 21 Sept
Great for Families! Brewster Home 6 Mi to Beach
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.

3. 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, (32 reviews)
"This house was a perfect place for us to stay during our trip exploring Cape Cod. It was centrally located to the various places we drove to and the proximity to the Cape Cod Rail Trail was great. The house is spacious and beautiful! It was clean and on a quiet street."
United States
Reba W.
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
A beach with footprints, a large rock, and a clear sky.

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

5. Beach Walks, Books & Bay Sunsets

Beach Walks, Books & Bay Sunsets
Brewster
The price is AU$1,010
includes taxes & fees
23 Sept - 24 Sept
Beach Walks, Books & Bay Sunsets
An outdoor seating area with wicker furniture and a fire pit, overlooking a calm lake and trees.

6. ★Waterfront & On Bike Path★Firepit ★Private beach★Bikes★Kayaks★Sm.Pet OK💥Sunsets

★Waterfront & On Bike Path★Firepit ★Private beach★Bikes★Kayaks★Sm.Pet OK💥Sunsets
West Brewster
10.0 out of 10, Exceptional, (29 reviews)
"The cottage is immaculate, has every amenity you would want and the host is very responsive. We absolutely loved our stay!"
United States
Katrina W.
The price is AU$2,204
includes taxes & fees
25 Sept - 26 Sept
★Waterfront & On Bike Path★Firepit ★Private beach★Bikes★Kayaks★Sm.Pet OK💥Sunsets
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

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 AU$689
includes taxes & fees
29 Sept - 30 Sept
Cozy Large Home in Harwich with Patio near Wequassett Resort
A room with a blue sofa, wicker chairs, a round table, a wall-mounted lamp, and a glass door leading outside.

8. 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 AU$818
includes taxes & fees
31 Aug - 1 Sept
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
A wooden-paneled room with a sofa, chairs, a table, a fireplace, and a clock.

9. 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 AU$656
includes taxes & fees
1 Sept - 2 Sept
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
A calm lake with a sandy beach, a sailboat, and a forested shoreline.

10. Dennis Beach House - Walk to Beach - Pet Friendly

Dennis Beach House - Walk to Beach - Pet Friendly
Dennis
8.0 out of 10, Very good, (10 reviews)
"Very cozy and quite neighborhood felt right at home."
United States
John S.
The price is AU$562
includes taxes & fees
13 Sept - 14 Sept
Dennis Beach House - Walk to Beach - Pet Friendly
A row of white buildings with storefronts, including a visible sign for 'Chatham' and a 'Chatham' sign above a window.

11. 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, (3 reviews)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is AU$693
includes taxes & fees
28 Sept - 29 Sept
Lovely House 5 Min to Beach with Deck, Grill, Garage
A covered porch with white railings and blue shutters, featuring two rocking chairs and a hanging flower basket.

12. 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.
The price is AU$1,300
includes taxes & fees
3 Sept - 4 Sept
New! 4BR Fire Pit, Ping Pong, Movie Room
A wooden deck with outdoor furniture, a covered seating area, and a view of neighboring houses.

13. 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 AU$647
includes taxes & fees
3 Sept - 4 Sept
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
A wooden deck with tables and chairs, surrounded by trees, overlooking a calm lake during sunset.

14. Luxe Lakefront Retreat★Sauna★Media Rm★Kayaks-SUPs★Bikes★Steps to BikePath★Pet OK

Luxe Lakefront Retreat★Sauna★Media Rm★Kayaks-SUPs★Bikes★Steps to BikePath★Pet OK
Harwich
10.0 out of 10, Exceptional, (2 reviews)
"I can't say enough about how special this property is! The house is gorgeous and everything is top of the line and pristine. Aruna the host is the absolute best so communicative and so sweet. We loved our stay so much and would stay again!"
United States
Susan G.
Luxe Lakefront Retreat★Sauna★Media Rm★Kayaks-SUPs★Bikes★Steps to BikePath★Pet OK
A single-story house with a front porch, a small deck, and a garden area with various plants.

15. Relaxing Cape Cod Cottage Getaway

Relaxing Cape Cod Cottage Getaway
Dennis
10.0 out of 10, Exceptional, (1 review)
"Clean and comfortable- Exactly what we needed for our trip to the Cape; we would definitely recommend!"
United States
Heathyr S.
The price is AU$1,004
includes taxes & fees
31 Aug - 1 Sept
Relaxing Cape Cod Cottage Getaway
A two-story house with a front porch, a chimney, and a well-maintained lawn.

16. 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 AU$1,098
includes taxes & fees
7 Sept - 8 Sept
Family Cottage Close to Beach!!
A sandy beach with a grassy path leading to the water.

17. 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 AU$1,038
includes taxes & fees
9 Sept - 10 Sept
Beautiful home near Jacknife Beach and bike trail
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.

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

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
Dennis
The price is AU$911
includes taxes & fees
25 Sept - 26 Sept
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
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

Lovely 3-bedroom house in Dennis perfect for a relaxing getaway
Dennis
The price is AU$817
includes taxes & fees
2 Sept - 3 Sept
Lovely 3-bedroom house in Dennis perfect for a relaxing getaway
An outdoor patio with Adirondack chairs, a fire pit, and string lights.

20. 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 AU$1,212
includes taxes & fees
2 Sept - 3 Sept
Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
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 Brewster Hotel Reviews

The Villages at Ocean Edge

The Villages at Ocean Edge

8/10 Good
"Clean room"
Timothy 2-night trip
Posted 3 hours ago
The Villages at Ocean Edge

Find out more about Brewster

Brewster Holiday Homes information

Number of reviews
378
Accommodation
147 Holiday Homes
Lowest Price
AU$562
Highest Price
AU$2,204