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

Brewster Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 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
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
$167 nightly
The price is $181
Nov 12 - Nov 13
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.
$307 nightly
The price is $333
Nov 12 - Nov 13
Total with taxes and fees
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 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
$114 nightly
The price is $131
Nov 12 - Nov 13
Total with taxes and fees
1 King Bed | Non-Smoking
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

4. 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.
$115 nightly
The price is $130
Nov 12 - Nov 13
Total with taxes and fees
Cozy private room in a shared home with a Full-size bed and private bathroom.
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.
$227 nightly
The price is $257
Nov 13 - Nov 14
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

6. "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.
$483 nightly
The price is $546
Nov 15 - Nov 16
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
A two-story house with a balcony, surrounded by lush greenery.

7. Quiet Solitude with Firepit, Electric Stove & Private Deck

Quiet Solitude with Firepit, Electric Stove & Private Deck
Hopewell Junction
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at Sara's place. Unfortunately due to all the rain we couldn't enjoy the outside facilities. The bedroom loft is charming and everything you need is there. Thanks for a great stay!"
United States
stephanie a.
$476 nightly
The price is $538
Nov 15 - Nov 16
Total with taxes and fees
Quiet Solitude with Firepit, Electric Stove & Private Deck
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

8. 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.
$288 nightly
The price is $293
Nov 15 - Nov 16
Total with taxes and fees
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".

9. Little Lake Cabin with Hot Tub and Fire Pit

Little Lake Cabin with Hot Tub and Fire Pit
New Fairfield
10.0 out of 10, Exceptional, (7 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.
$437 nightly
The price is $498
Nov 16 - Nov 17
Total with taxes and fees
Little Lake Cabin with Hot Tub and Fire Pit
A modern hotel room with a bed, bedside table, lamp, desk, and window.

10. 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
$109 nightly
The price is $125
Nov 16 - Nov 17
Total with taxes and fees
1 Queen Bed | Non-Smoking
A brick building with a sign reading 'Lobby' in front.

11. 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
$79 nightly
The price is $91
Nov 24 - Nov 25
Total with taxes and fees
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Living area

12. 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.
$176 nightly
The price is $193
Nov 12 - Nov 13
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
A hotel room with two beds, a desk, a chair, and a large window with curtains.

13. 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
$119 nightly
The price is $136
Nov 12 - Nov 13
Total with taxes and fees
2 Queen Beds | Non-Smoking
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

14. 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
$71 nightly
The price is $80
Nov 22 - Nov 23
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

15. Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
$233 nightly
The price is $258
Nov 12 - Nov 13
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A white house with a wooden staircase leading to a porch.

16. 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
$116 nightly
The price is $131
Dec 1 - Dec 2
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
A dining area with a table, chairs, a vase with flowers, a hanging light fixture, and wall decorations.

17. Mountain-View 2BR Steps from Thayer Gate

Mountain-View 2BR Steps from Thayer Gate
Highland Falls
$302 nightly
The price is $337
Nov 15 - Nov 16
Total with taxes and fees
Mountain-View 2BR Steps from Thayer Gate
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.
$324 nightly
The price is $360
Dec 8 - Dec 9
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
A modern bedroom with a blue sofa, a bed, a TV, and a window with a view.

19. Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Beacon
10.0 out of 10, Exceptional, (57 reviews)
"Great location. Very walkable. Highly recommend."
United States
Maryanne
$211 nightly
The price is $243
Nov 23 - Nov 24
Total with taxes and fees
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
A living room with a wooden floor, a black sofa, a coffee table, and a ceiling fan.

20. Perfect 2BR with Free Parking! Walk to West Point!

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
$290 nightly
The price is $322
Nov 16 - Nov 17
Total with taxes and fees
Perfect 2BR with Free Parking! Walk to West Point!
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
"The place and staff were exceptional."
Nomi 3-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Danbury

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 $91 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.