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

Brewster Vacation Rentals

  • 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
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Brewster vacation rentals

A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

1. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
7.4 out of 10, Good, (3 reviews)
"We had a wonderful experience! The RV was very nice and cozy. Everything was clean and well maintained. The property was beautiful. The host was very helpful and accommodating. Definitely plan on coming back!"
United States
Fernanda
The price is AED 386
AED 665 total
includes taxes & fees
7 Nov - 8 Nov
Welcome to Sweet Abby Rose!
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

2. 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 AED 612
AED 1,228 total
includes taxes & fees
9 Nov - 10 Nov
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A modern hotel room with a bed, bedside table, lamp, desk, and window.

3. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Bethel
10.0 out of 10, Exceptional, (4 reviews)
"Quick check-in and a quiet room made sleeping easy here. Everything felt straightforward without hassle."
United States
Anonymous traveler
The price is AED 402
AED 463 total
includes taxes & fees
8 Nov - 9 Nov
1 Queen Bed | Non-Smoking
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

4. "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, (5 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is AED 727
AED 1,928 total
includes taxes & fees
11 Nov - 12 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.

5. 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 AED 621
AED 981 total
includes taxes & fees
8 Nov - 9 Nov
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

6. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is AED 452
AED 1,098 total
includes taxes & fees
9 Nov - 10 Nov
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

7. The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (6 reviews)
"Great location and lots to do despite it raining for half our stay! My dog enjoyed the yard and walks around the neighborhood. My son loved kayaking and having his first ever s’more. Honestly I wished we had booked a longer trip! "
United States
Lyndsey F.
The price is AED 1,100
AED 1,935 total
includes taxes & fees
8 Nov - 9 Nov
The Little Lake Cabin with hot tub
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

8. 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 AED 231
AED 479 total
includes taxes & fees
18 Nov - 19 Nov
Cozy private room in a shared home with a Full-size bed and private bathroom.
A brick building with a sign reading 'Lobby' in front.

9. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveler
The price is AED 291
AED 336 total
includes taxes & fees
24 Nov - 25 Nov
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A modern hotel room with a bed, bedside table, lamp, desk, and window.

10. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Bethel
10.0 out of 10, Exceptional, (3 reviews)
"We found plenty of space for our small group plus pets. Loved having a private bathroom,it made mornings smooth."
United States
Anonymous traveler
The price is AED 420
AED 483 total
includes taxes & fees
7 Nov - 8 Nov
1 King Bed | Non-Smoking
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

11. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (19 reviews)
"Great rooms and service,"
United States
Anonymous traveler
The price is AED 291
AED 329 total
includes taxes & fees
5 Dec - 6 Dec
1 King Bed | Non-Smoking, Kitchen, Shower
A hotel room with two beds, a desk, a chair, and a large window with curtains.

12. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Bethel
10.0 out of 10, Exceptional, (2 reviews)
"Got a good rest before the drive. Place was clean with a refreshing shower and calm enough for sleep."
United States
Anonymous traveler
The price is AED 438
AED 504 total
includes taxes & fees
7 Nov - 8 Nov
2 Queen Beds | Non-Smoking
A white house with a wooden staircase leading to a porch.

13. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (39 reviews)
"Charles was super responsive and the bed was amazingly comfortable. Also the shower head great water pressure :-)"
United States
Lisbeth
The price is AED 380
AED 481 total
includes taxes & fees
1 Dec - 2 Dec
Cozy One Bedroom Apartment Centrally Located in Southbury
Living area

14. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
8.4 out of 10, Very good, (5 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is AED 378
AED 708 total
includes taxes & fees
8 Nov - 9 Nov
Cozy 1-bedroom retreat minutes from West Point!
A blue house with a white porch, a welcome sign, and a mailbox.

15. 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 AED 518
AED 1,719 total
includes taxes & fees
10 Nov - 11 Nov
3BR West Point Retreat-3min to Back Gate+ King Bed
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

16. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean rooms, Diner down the block, family friendly, communication was prompt and clear"
United States
Joseph
The price is AED 921
AED 1,362 total
includes taxes & fees
13 Nov - 14 Nov
Rustic Cabin in Fishkill!
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

17. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (42 reviews)
"We’ve actually stayed here twice so that should tell you we enjoy the space and the host is lovely."
United States
Heather M.
The price is AED 826
AED 1,470 total
includes taxes & fees
8 Nov - 9 Nov
Contemporary Cozy Cottage
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

18. 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 AED 566
AED 1,065 total
includes taxes & fees
8 Nov - 9 Nov
Fabulous 3bdrm Home w/parking!
A wooden coffee table with two decorative planters in a living room.

19. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
The price is AED 566
AED 987 total
includes taxes & fees
8 Nov - 9 Nov
Walk to WP Gate + Free Parking!
A living room with a fireplace, two armchairs, a sofa, and a TV.

20. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
The price is AED 546
AED 672 total
includes taxes & fees
9 Nov - 10 Nov
Mid Century Modern Studio w/ Full Kitchen - Newly Built
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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"The staff was very helpful when we had a dog barking at night. The room was very clean. We really enjoyed walking around the lake, When we complained about a cold shower it was fixed by the next day."
Christa 2-night trip
Posted 16 hours ago
Overlook Lodge at Bear Mountain

Frequently asked questions

Can I find a vacation rental in Brewster?

Yes, we offer vacation rentals close to popular local attractions in Brewster, or you can choose a secluded option if you're looking for a relaxing stay. Brewster is known for its shopping and restaurants. Make sure you have time to check out the entertainment choices and live music during your trip.

What's the top vacation rental that Brewster has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental outside of Brewster offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Brewster?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Brewster stay.

What’s there to see and do in Brewster?

Explore the area and cultural attractions such as Ives Concert Park, or visit a family-friendly sight such as SplashDown Beach. Other places in town to visit include Wells Park and Brewster Public Library.

What’s a vacation rental in Brewster like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Brewster. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for families.