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

Brewster Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Brewster holiday 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
10.0 out of 10, Exceptional, (2 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 HK$785
HK$1,454 total
includes taxes & fees
18 Oct - 19 Oct
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 HK$1,452
HK$2,926 total
includes taxes & fees
3 Nov - 4 Nov
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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 HK$1,568
HK$4,508 total
includes taxes & fees
21 Oct - 22 Oct
"Country outside the city " 3 bedrooms 2 full bathrooms
Step up to a warm welcome - our charming entryway, complete with a hanging birdhouse, sets the tone for a peaceful stay.

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, (25 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is HK$1,646
HK$4,285 total
includes taxes & fees
20 Oct - 21 Oct
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
A picnic setup with a checkered blanket, a basket, and two wine glasses on a grassy area with a lake and trees in the background.

5. Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
New Fairfield
8.6 out of 10, Excellent, (36 reviews)
"Very serene location, the host was very responsive and helpful."
United States
Stephen L.
The price is HK$826
HK$2,508 total
includes taxes & fees
18 Oct - 19 Oct
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

6. 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 HK$1,326
HK$2,193 total
includes taxes & fees
19 Oct - 20 Oct
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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, (5 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 HK$2,270
HK$4,231 total
includes taxes & fees
20 Oct - 21 Oct
The Little Lake Cabin with hot tub
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

8. 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 traveller
The price is HK$622
HK$704 total
includes taxes & fees
26 Oct - 27 Oct
1 King Bed | Non-Smoking, Kitchen, Shower
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
9.2 out of 10, Wonderful, (20 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is HK$621
HK$717 total
includes taxes & fees
12 Nov - 13 Nov
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

10. 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 HK$887
HK$2,393 total
includes taxes & fees
5 Nov - 6 Nov
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A modern hotel room with a large bed, bedside tables, a desk, and a chair.

11. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Bethel
The price is HK$858
HK$987 total
includes taxes & fees
18 Oct - 19 Oct
1 Queen Bed | Non-Smoking
A white house with a wooden staircase leading to a porch.

12. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is HK$812
HK$1,091 total
includes taxes & fees
18 Oct - 19 Oct
Cozy One Bedroom Apartment Centrally Located in Southbury
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

13. 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 HK$1,209
HK$2,392 total
includes taxes & fees
19 Oct - 20 Oct
Fabulous 3bdrm Home w/parking!
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

14. 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 HK$981
HK$3,173 total
includes taxes & fees
20 Oct - 21 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

15. 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 HK$1,766
HK$3,205 total
includes taxes & fees
18 Oct - 19 Oct
Contemporary Cozy Cottage
A house with a view of a bridge and mountains.

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, (148 reviews)
"We had a great stay!!"
United States
Jasmine
The price is HK$1,554
HK$2,595 total
includes taxes & fees
9 Nov - 10 Nov
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

17. 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 HK$1,968
HK$3,065 total
includes taxes & fees
6 Nov - 7 Nov
Rustic Cabin in Fishkill!
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

18. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (20 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
The price is HK$1,067
HK$3,512 total
includes taxes & fees
21 Oct - 22 Oct
Local Artist Inspired | Walk to WestPoint + King Bed
A modern kitchen with a dining area, large windows, and a TV displaying a streaming service.

19. 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, (6 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is HK$1,187
HK$1,869 total
includes taxes & fees
28 Oct - 29 Oct
The Perch in the Purchase -- Cozy, unique, and private
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

20. 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 HK$530
HK$1,127 total
includes taxes & fees
3 Nov - 4 Nov
Cozy private room in a shared home with a Full-size bed and private bathroom.
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

La Quinta Inn & Suites by Wyndham Danbury

La Quinta Inn & Suites by Wyndham Danbury

10/10 Excellent
"Breakfast was good. The room was very clean."
Anish 1-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Danbury

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
  • Use the map to find apartments and other holiday homes in the Brewster neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Brewster while they last

Look no further and take a look at our great range of rental properties in Brewster!

Frequently asked questions

Can I find a holiday rental in Brewster?

Yes, there are holiday rentals close to the most popular sights in Brewster, or you can select a more 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 are some of the best holiday rentals that Brewster has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Brewster offers a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Brewster?

With 3 Expedia holiday rentals, you're guaranteed 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 one of the family-friendly sights such as SplashDown Beach. Other places in town to visit include Wells Park and Brewster Public Library.

What’s a holiday rental in Brewster like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Brewster. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.