A windmill in a grassy field with trees in the background.

Search Vacation Homes in Brewster

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Brewster vacation 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 ￥26,335
￥55,453 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥10,579
￥22,511 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥31,460
￥91,237 total
includes taxes & fees
Nov 2 - Nov 3
"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 ￥26,487
￥44,147 total
includes taxes & fees
Oct 26 - Oct 27
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A multi-story house with a dock and boats, surrounded by dense forest.

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 ￥53,472
￥194,698 total
includes taxes & fees
Oct 26 - Oct 27
North Cliff House - Private Dock & Sauna
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

6. 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 ￥41,471
￥104,307 total
includes taxes & fees
Oct 25 - Oct 26
Renovated Retreat with Heated Pool
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

7. 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 ￥35,264
￥63,996 total
includes taxes & fees
Oct 26 - Oct 27
Contemporary Cozy Cottage
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

8. 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 ￥20,404
￥65,452 total
includes taxes & fees
Oct 27 - Oct 28
House on the Babbling Brook- Quiet 2BR + King Bed!
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 ￥36,205
￥63,545 total
includes taxes & fees
Nov 17 - Nov 18
Fabulous 3bdrm Home w/parking!
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

10. 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 ￥38,117
￥85,145 total
includes taxes & fees
Nov 4 - Nov 5
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

11. 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 ￥28,211
￥78,984 total
includes taxes & fees
Nov 1 - Nov 2
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A blue house with a white porch, a welcome sign, and a mailbox.

12. 3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very good, (7 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is ￥26,331
￥82,956 total
includes taxes & fees
Oct 27 - Oct 28
3BR West Point Retreat-3min to Back Gate+ King Bed
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

13. 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 ￥60,341
￥88,364 total
includes taxes & fees
Nov 3 - Nov 4
Hickory on Willow Lake
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 ￥43,101
￥65,545 total
includes taxes & fees
Nov 12 - Nov 13
Red Cottage - Lakeside Property!
A room with a wooden floor, a white door with a number, and a window with blinds.

15. 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 ￥33,572
￥61,818 total
includes taxes & fees
Nov 17 - Nov 18
Lovely 3BR Home with parking-Walk to WP Gate!
An outdoor patio area with a covered seating area, a pool, and potted plants.

16. 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 ￥41,322
￥54,180 total
includes taxes & fees
Oct 28 - Oct 29
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A bedroom with a bed, a dresser, and a window with curtains.

17. 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 ￥82,283
￥136,551 total
includes taxes & fees
Oct 26 - Oct 27
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A modern kitchen with stainless steel appliances, a marble countertop, and a dining area with white chairs.

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

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is ￥39,671
￥71,048 total
includes taxes & fees
Oct 28 - Oct 29
Hudson Valley/West Point Retreat w/ parking!
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 ￥60,341
￥84,197 total
includes taxes & fees
Nov 20 - Nov 21
Chestnut on Willow Lake
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

20. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is ￥62,517
￥135,079 total
includes taxes & fees
Nov 3 - Nov 4
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Brewster Hotel Reviews

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

10/10 Excellent
"The room was clean The staff were helpful. My key didn’t unlock the door one night but the staff fixed it with no problems. Breakfast was good but was the exact same menu for each day The air conditioning system worked"
Dawn 2-night trip
Posted 12 hours ago
Comfort Suites Fishkill near Interstate 84

Find out more about Brewster

Brewster Vacation Homes information

Number of reviews
240
Accommodation
238 Vacation Homes
Lowest Price
￥22,511
Highest Price
￥194,698