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Holiday Homes in Brewster

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Brewster holiday homes

A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

1. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is €365
includes taxes & fees
9 Nov - 10 Nov
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

2. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"I really enjoyed my four night stay here."
United States
Jim B.
The price is €132
includes taxes & fees
9 Nov - 10 Nov
Cozy private room in a shared home with a Full-size bed and private bathroom.
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

3. "Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is €516
includes taxes & fees
2 Nov - 3 Nov
"Country outside the city " 3 bedrooms 2 full bathrooms
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

4. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is €255
includes taxes & fees
25 Oct - 26 Oct
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A covered outdoor area with a view of a lake, stone steps, and a grill.

5. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, Exceptional, (9 reviews)
"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"
United States
Ron P.
The price is €1,122
includes taxes & fees
26 Oct - 27 Oct
North Cliff House - Private Dock & Sauna
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

6. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (41 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is €379
includes taxes & fees
25 Oct - 26 Oct
Contemporary Cozy Cottage
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

7. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (14 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
The price is €401
includes taxes & fees
26 Oct - 27 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

8. Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is €602
includes taxes & fees
25 Oct - 26 Oct
Renovated Retreat with Heated Pool
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

9. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
The price is €355
includes taxes & fees
17 Nov - 18 Nov
Fabulous 3bdrm Home w/parking!
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

10. Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Great location and super host. "
United States
James U.
The price is €466
includes taxes & fees
1 Nov - 2 Nov
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

11. Hickory on Willow Lake

Hickory on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean, quiet and great location. Beautiful property."
United States
Sheila B.
The price is €493
includes taxes & fees
21 Nov - 22 Nov
Hickory on Willow Lake
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

12. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay at the lake house. The home is beautiful inside and out, and there is every amenity you could think of, from cooking and cleaning supplies to extra towels and blankets. The view of the lake is stunning and we enjoyed the peace and quiet of the little community. Linh is an excellent host and helped answer all of our questions. We will definitely be back!"
United States
Angel R.
The price is €499
includes taxes & fees
2 Nov - 3 Nov
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A room with a wooden floor, a white door with a number, and a window with blinds.

13. Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is €346
includes taxes & fees
17 Nov - 18 Nov
Lovely 3BR Home with parking-Walk to WP Gate!
A lakeside seating area with Adirondack chairs arranged around a central fire pit.

14. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is €379
includes taxes & fees
21 Nov - 22 Nov
Red Cottage - Lakeside Property!
An outdoor patio area with a covered seating area, a pool, and potted plants.

15. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (81 reviews)
"The property was as advertised and met our needs for our trip."
United States
Sara
The price is €304
includes taxes & fees
28 Oct - 29 Oct
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A bedroom with a bed, a dresser, and a window with curtains.

16. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
New Milford
10.0 out of 10, Exceptional, (1 review)
"Perfect!!"
United States
Jeni O.
The price is €773
includes taxes & fees
28 Oct - 29 Oct
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A kitchen with a coffee maker, toaster, and two mugs on a marble countertop.

17. Hudson Valley/West Point Retreat w/ parking!

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is €467
includes taxes & fees
17 Nov - 18 Nov
Hudson Valley/West Point Retreat w/ parking!
A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

18. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
Ossining
8.2 out of 10, Very good, (19 reviews)
"A family trip with teens and tweens- a perfect space! Clean, hist was friendly, the house was stocked with all we'd need! A great getaway for any family NYC trip!"
United States
Justeen P.
Snow Days & City Escapes: Spacious Ossining Home
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

19. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed a relaxing weekend before R-day at West Point and it was perfect! A beautiful property and we hope to be back another time!"
United States
Quintina R.
The price is €486
includes taxes & fees
21 Nov - 22 Nov
Chestnut on Willow Lake
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

20. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is €904
includes taxes & fees
3 Nov - 4 Nov
Summer Pool Oasis Custom Bar Arcade Pool Table
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

Inn on the Hudson

Inn on the Hudson

8/10 Good
"Slightly dated hotel walkable into the town centre have used before and would use again"
Paul 1-night trip
Posted 19 hours ago
Inn on the Hudson

Find out more about Brewster

Brewster Holiday Homes information

Number of reviews
249
Accommodation
198 Holiday Homes
Lowest Price
€132
Highest Price
€1,122