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Brewster Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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 ￥15,936
￥29,705 total
includes taxes & fees
Sep 2 - Sep 3
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, (20 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥38,181
￥71,046 total
includes taxes & fees
Sep 8 - Sep 9
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 ￥16,809
￥32,054 total
includes taxes & fees
Aug 30 - Aug 31
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Exterior detail

4. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Walk-to-Lake Cottage With Grill for Peaceful Fall 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 ￥25,165
￥76,576 total
includes taxes & fees
Sep 3 - Sep 4
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Private kitchen

5. 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
The price is ￥10,836
￥22,979 total
includes taxes & fees
Sep 2 - Sep 3
Cozy private room in a shared home with a Full-size bed and private bathroom.
Exterior

6. 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 ￥13,079
￥15,123 total
includes taxes & fees
Sep 9 - Sep 10
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
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 ￥35,856
￥97,168 total
includes taxes & fees
Sep 15 - Sep 16
"Country outside the city " 3 bedrooms 2 full bathrooms
Interior

8. 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 ￥36,340
￥48,233 total
includes taxes & fees
Sep 28 - Sep 29
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Exterior

9. 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 ￥14,120
￥19,440 total
includes taxes & fees
Sep 20 - Sep 21
Cozy One Bedroom Apartment Centrally Located in Southbury
Outdoor dining

10. 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 ￥23,235
￥37,278 total
includes taxes & fees
Sep 2 - Sep 3
The Perch in the Purchase -- Cozy, unique, and private
Property grounds

11. 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 ￥17,530
￥32,991 total
includes taxes & fees
Sep 7 - Sep 8
Hoppy Hill Farm House
Lobby

12. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (18 reviews)
"Great rooms and service,"
United States
Anonymous traveler
The price is ￥11,769
￥13,314 total
includes taxes & fees
Sep 17 - Sep 18
1 King Bed | Non-Smoking, Kitchen, Shower
Exterior

13. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (5 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is ￥48,206
￥73,136 total
includes taxes & fees
Sep 1 - Sep 2
Rustic Cabin in Fishkill!
TV

14. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (25 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
The price is ￥23,192
￥43,345 total
includes taxes & fees
Aug 31 - Sep 1
Walk to WP Gate + Free Parking!
Smart TV, fireplace, video games, DVD player

15. 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 ￥95,457
￥167,524 total
includes taxes & fees
Sep 11 - Sep 12
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Property grounds

16. 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 ￥31,553
￥53,462 total
includes taxes & fees
Sep 1 - Sep 2
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
TV

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

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
9.0 out of 10, Wonderful, (4 reviews)
"Visiting West Point for ring weekend. Location was great and the reason we chose the place. Property itself could really use some TLC, but it met our needs. Communication with the owner was good and gaining access to the property was straightforward. Would consider staying here again just based on the close proximity to West Point."
United States
Kevin
The price is ￥22,439
￥40,665 total
includes taxes & fees
Sep 1 - Sep 2
Cozy 1-bedroom retreat minutes from West Point!
Outdoor dining

18. 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 ￥41,633
￥54,957 total
includes taxes & fees
Sep 1 - Sep 2
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

19. Glamping, family fun, pet friendly

Glamping, family fun, pet friendly
Dover Plains
10.0 out of 10, Exceptional, (5 reviews)
"Great Glamping spot. The hosts were very responsive and the place provided many activities. "
United States
Gui
The price is ￥12,765
￥21,292 total
includes taxes & fees
Sep 2 - Sep 3
Glamping, family fun, pet friendly
Dining

20. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
The price is ￥25,742
￥54,526 total
includes taxes & fees
Sep 2 - Sep 3
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
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

The Watershed

The Watershed

10/10 Excellent
"Such a chic hotel just an hour out of NY and directly off the Merritt Pkwy. Great Italian restaurant at the property. Staff were friendly and helpful. Will stay again when I’m headed into the city."
Rachael 1-night trip
Posted 6 hours ago
The Watershed

Find out more about Brewster

Search for holiday rentals in Brewster on Expedia! You can easily find your home rentals, villas, holiday apartments in Brewster using one of the methods below:

  • View our selection of featured holiday rentals in Brewster
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Look no further and take a look at our great range of rental properties in Brewster!

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.