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

Brewster Vacation Rentals

Check prices for these dates

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

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
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
$171 nightly
The price is $185
Oct 18 - Oct 19
Total with taxes and fees
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.
$344 nightly
The price is $373
Nov 3 - Nov 4
Total with taxes and fees
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.
$508 nightly
The price is $574
Oct 21 - Oct 22
Total with taxes and fees
"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.
$495 nightly
The price is $546
Oct 20 - Oct 21
Total with taxes and fees
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
A bedroom with a large bed, a bedside table with a lamp, a potted plant, and a mirror on the wall.

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.
$281 nightly
The price is $320
Oct 18 - Oct 19
Total with taxes and fees
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.
$247 nightly
The price is $279
Oct 19 - Oct 20
Total with taxes and fees
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.
$506 nightly
The price is $573
Oct 26 - Oct 27
Total with taxes and fees
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 traveler
$79 nightly
The price is $90
Oct 26 - Oct 27
Total with taxes and fees
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 traveler
$79 nightly
The price is $92
Nov 1 - Nov 2
Total with taxes and fees
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.
$289 nightly
The price is $297
Nov 15 - Nov 16
Total with taxes and fees
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
$110 nightly
The price is $126
Oct 18 - Oct 19
Total with taxes and fees
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.
$124 nightly
The price is $139
Oct 18 - Oct 19
Total with taxes and fees
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.
$275 nightly
The price is $305
Oct 19 - Oct 20
Total with taxes and fees
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.
$378 nightly
The price is $404
Oct 20 - Oct 21
Total with taxes and fees
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.
$357 nightly
The price is $408
Oct 18 - Oct 19
Total with taxes and fees
Contemporary Cozy Cottage
A tree in the foreground with a view of a forested landscape in the background.

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
$279 nightly
The price is $330
Oct 20 - Oct 21
Total with taxes and fees
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
$343 nightly
The price is $390
Nov 6 - Nov 7
Total with taxes and fees
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.
$436 nightly
The price is $448
Oct 21 - Oct 22
Total with taxes and fees
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
$210 nightly
The price is $238
Oct 28 - Oct 29
Total with taxes and fees
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.
$128 nightly
The price is $144
Nov 3 - Nov 4
Total with taxes and fees
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

Comfort Inn & Suites Danbury-Bethel

Comfort Inn & Suites Danbury-Bethel

8/10 Good
"Breakfasts are good except the bananas"
Arthur 4-night trip
Posted 16 hours ago
Comfort Inn & Suites Danbury-Bethel

Find out more about Brewster

Everything you need to know about Brewster vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Brewster vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Brewster vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Brewster vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Brewster. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Brewster in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $92 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Brewster rentals

At Expedia, we put the best Brewster vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Brewster rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Brewster vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Brewster. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.