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Holiday Homes in Brewster

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

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
9.8 out of 10, Exceptional, (20 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is €388
includes taxes & fees
21 Sept - 22 Sept
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, (1 review)
"Clean and close to activitys"
United States
randall
The price is €128
includes taxes & fees
7 Sept - 8 Sept
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 €511
includes taxes & fees
15 Sept - 16 Sept
"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 €248
includes taxes & fees
7 Sept - 8 Sept
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A room with a bed, a couch, a desk with a computer, and various wall decorations.

5. Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
The price is €248
includes taxes & fees
5 Oct - 6 Oct
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
A spacious living room with a foosball table, a large flat-screen TV, and a fireplace.

6. Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Place was beautifully done, it’s obvious they take care of their place. The hosts were thoughtful and attentive, will definitely visit again. "
United States
Jasmine G.
The price is €899
includes taxes & fees
8 Sept - 9 Sept
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
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
10.0 out of 10, Exceptional, (11 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is €345
includes taxes & fees
8 Sept - 9 Sept
House on the Babbling Brook- Quiet 2BR + King Bed!
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

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

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
The price is €453
includes taxes & fees
20 Sept - 21 Sept
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.

9. 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 €387
includes taxes & fees
7 Sept - 8 Sept
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A blue house with a white porch, a welcome sign, and a mailbox.

10. 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 €429
includes taxes & fees
8 Sept - 9 Sept
3BR West Point Retreat-3min to Back Gate+ King Bed
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

11. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (40 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 €394
includes taxes & fees
30 Sept - 1 Oct
Contemporary Cozy Cottage
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

12. Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is €716
includes taxes & fees
27 Sept - 28 Sept
Renovated Retreat with Heated Pool
An outdoor patio area with a covered seating area, a pool, and potted plants.

13. 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, (74 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is €299
includes taxes & fees
7 Sept - 8 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

14. 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 €389
includes taxes & fees
29 Sept - 30 Sept
Fabulous 3bdrm Home w/parking!
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 €381
includes taxes & fees
9 Sept - 10 Sept
Lovely 3BR Home with parking-Walk to WP Gate!
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

16. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is €603
includes taxes & fees
8 Sept - 9 Sept
Chestnut on Willow Lake
A patio with a round table and chairs, overlooking a body of water and a forested area during sunset.

17. Candlewood Lake Retreat with Private Dock

Candlewood Lake Retreat with Private Dock
New Milford
10.0 out of 10, Exceptional, (59 reviews)
"Great property for a family to enjoy the lake!"
United States
Jenny B.
The price is €1,578
includes taxes & fees
17 Sept - 18 Sept
Candlewood Lake Retreat with Private Dock
A room with a Yale banner, a white robe hanging on a rack, and a light switch on the wall.

18. 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
The price is €623
includes taxes & fees
9 Sept - 10 Sept
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A bedroom with two beds, a nightstand with a lamp, a framed picture on the wall, and a window with curtains.

19. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is €364
includes taxes & fees
28 Sept - 29 Sept
Gilded Age Luxury Surrounded by Nature
A modern kitchen with a large island, white cabinetry, stainless steel appliances, and a view through large windows.

20. Private Country Getaway

Private Country Getaway
Bedford Hills
9.6 out of 10, Exceptional, (4 reviews)
"We had a busy and lovely weekend to attend and be part of my nieces wedding. The location was perfect and the property is beautiful. Kitchen was perfect for gathering in the morning and the great room was big and comfy for catching up! "
United States
Karin R.
The price is €1,813
includes taxes & fees
12 Sept - 13 Sept
Private Country Getaway
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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"I love staying at Bear mountain. The cottages are sometimes disappointing depending on which unit you get. This time the temperature was cold at night and there are no controls to regulate it. The building is regulated by one thermostat which is only controlled the facility. Also the bathroom was ridiculously small. The door opened in and if the door was open there literally was no room to actually stand in the bathroom. Smaller than the bathroom in my camper."
Sandra 2-night trip
Posted less than an hour ago
Overlook Lodge at Bear Mountain

Find out more about Brewster

Brewster Holiday Homes information

Number of reviews
262
Accommodation
247 Holiday Homes
Lowest Price
€128
Highest Price
€1,813