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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Brewster vacation rentals

1 bedroom, internet, bed sheets

1. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (1 review)
"The place is super comfortable and has a great outdoor area for chatting; I would definitely like to come back and stay longer."
United States
Yasmin G.
The price is SAR 375
SAR 700 total
includes taxes & fees
24 Aug - 25 Aug
Welcome to Sweet Abby Rose!
TV, fireplace

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
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is SAR 1,032
SAR 1,839 total
includes taxes & fees
9 Sep - 10 Sep
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Exterior

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

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (12 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is SAR 394
SAR 756 total
includes taxes & fees
18 Aug - 19 Aug
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Interior

4. 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 SAR 541
SAR 749 total
includes taxes & fees
14 Sep - 15 Sep
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Exterior detail

5. Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (24 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is SAR 822
SAR 2,106 total
includes taxes & fees
18 Aug - 19 Aug
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
1 bedroom, WiFi (free)

6. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
9.6 out of 10, Exceptional, (21 reviews)
"Worst hotel experience I have ever had. Grounds were unkept. No one was at the front desk when I first arrived. Waited 20 minutes for someone to arrive and had to leave for dinner. Came back to find out that they were overbooked."
United States
Glenn
The price is SAR 306
SAR 347 total
includes taxes & fees
1 Sep - 2 Sep
2 Queen Beds | Non-Smoking, Kitchen
Coffee/tea maker, fridge, microwave, oven

7. "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 SAR 818
SAR 2,271 total
includes taxes & fees
24 Aug - 25 Aug
"Country outside the city " 3 bedrooms 2 full bathrooms
Exterior

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

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (19 reviews)
"Great place to stay,"
United States
Anonymous traveler
The price is SAR 276
SAR 319 total
includes taxes & fees
1 Sep - 2 Sep
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Smart TV, fireplace, video games, DVD player

9. 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 SAR 2,249
SAR 3,943 total
includes taxes & fees
18 Aug - 19 Aug
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Property grounds

10. Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"The accommodations were wonderful and comfortable."
United States
Chuck S.
The price is SAR 413
SAR 777 total
includes taxes & fees
7 Sep - 8 Sep
Hoppy Hill Farm House
TV

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

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (3 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 SAR 552
SAR 984 total
includes taxes & fees
9 Sep - 10 Sep
Cozy 1-bedroom retreat minutes from West Point!
Coffee/tea maker, fridge, microwave, oven

12. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (37 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 SAR 845
SAR 1,597 total
includes taxes & fees
18 Aug - 19 Aug
Contemporary Cozy Cottage
Property grounds

13. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (141 reviews)
"We had a great stay!!"
United States
Jasmine
The price is SAR 743
SAR 1,260 total
includes taxes & fees
18 Aug - 19 Aug
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior

14. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (36 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
The price is SAR 348
SAR 475 total
includes taxes & fees
8 Sep - 9 Sep
Cozy One Bedroom Apartment Centrally Located in Southbury
Property grounds

15. Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (9 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
The price is SAR 301
SAR 502 total
includes taxes & fees
18 Aug - 19 Aug
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Outdoor dining

16. 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 SAR 1,027
SAR 2,149 total
includes taxes & fees
24 Aug - 25 Aug
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Outdoor dining

17. The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is SAR 547
SAR 878 total
includes taxes & fees
25 Aug - 26 Aug
The Perch in the Purchase -- Cozy, unique, and private
Desk, WiFi (free), bed sheets

18. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (2 reviews)
"Great stay!"
United States
Ann S.
The price is SAR 671
SAR 1,274 total
includes taxes & fees
24 Aug - 25 Aug
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Lobby

19. 1 Queen Bed | ADA/RI Shower/Nsmk/Kitchen

1 Queen Bed | ADA/RI Shower/Nsmk/Kitchen
Fishkill
10.0 out of 10, Exceptional, (15 reviews)
"Good so far"
United States
Anonymous traveler
The price is SAR 306
SAR 347 total
includes taxes & fees
1 Sep - 2 Sep
1 Queen Bed | ADA/RI Shower/Nsmk/Kitchen
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 Inn & Suites Danbury-Bethel

Comfort Inn & Suites Danbury-Bethel

10/10 Excellent
"The room was very clean and all the staff were very friendly!"
Debra 1-night trip
Posted 2 hours ago
Comfort Inn & Suites Danbury-Bethel

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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental outside of Brewster offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and an electric kettle, 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 Brewster Public Library and Wells Park.

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.