Brewster Vacation Rentals

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Our top choices for Brewster vacation rentals

The Hideaway

The Hideaway
Brewster
10.0 out of 10, Exceptional, (8 reviews)
"Nice, clean, comfortable place to stay. Beautiful, convenient setting. Will look to come back again some day for sure. "
United States
Kenneth M.
$285 nightly
The price is $309
May 25 - May 26
Total with taxes and fees
The Hideaway

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, (7 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.
$118 nightly
The price is $134
May 25 - May 26
Total with taxes and fees
Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Glamping, family fun, pet friendly

Glamping, family fun, pet friendly
Dover Plains
10.0 out of 10, Exceptional, (4 reviews)
"Great Glamping spot. The hosts were very responsive and the place provided many activities. "
United States
Gui
$118 nightly
The price is $134
May 25 - May 26
Total with taxes and fees
Glamping, family fun, pet friendly

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (27 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
$112 nightly
The price is $126
May 25 - May 26
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury

1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
10.0 out of 10, Exceptional, (16 reviews)
"Great rooms and service,"
United States
Anonymous traveler
$90 nightly
The price is $102
Jun 17 - Jun 18
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"Location was great. Accommodations were clean and comfortable. Host was accessible and responsive. Will stay here again if in the area again."
United States
Ken K.
$180 nightly
The price is $204
May 25 - May 26
Total with taxes and fees
Hoppy Hill Farm House

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Carmel
10.0 out of 10, Exceptional, (7 reviews)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
United States
Varuna S.
$207 nightly
The price is $224
May 25 - May 26
Total with taxes and fees
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
$505 nightly
The price is $622
Jun 2 - Jun 3
Total with taxes and fees
Updated Home w/ Patio Half Mile to West Point

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Beacon
10.0 out of 10, Exceptional, (36 reviews)
"Great location, clean, overall terrific!"
United States
Daniel M.
$209 nightly
The price is $241
Jun 1 - Jun 2
Total with taxes and fees
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

1 Queen Bed | ADA/RI Shower/Smoking/Kitchen

1 Queen Bed | ADA/RI Shower/Smoking/Kitchen
Fishkill
10.0 out of 10, Exceptional, (15 reviews)
"Good so far"
United States
Anonymous traveler
$90 nightly
The price is $102
Jun 17 - Jun 18
Total with taxes and fees
1 Queen Bed | ADA/RI Shower/Smoking/Kitchen

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
$254 nightly
The price is $275
May 22 - May 23
Total with taxes and fees
Charming 1-bedroom apartment in Carmel with WiFi, AC

Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.6 out of 10, Exceptional, (4 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
$623 nightly
The price is $712
May 25 - May 26
Total with taxes and fees
Chestnut on Willow Lake

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (47 reviews)
"Great place to stay. Cozy, warm, and clean! The host was also a good communicator and everything went smoothly."
United States
Samantha Esmé W.
$211 nightly
The price is $243
May 27 - May 28
Total with taxes and fees
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
$1,321 nightly
The price is $1,471
May 28 - May 29
Total with taxes and fees
Summer Pool Oasis Custom Bar Arcade Pool Table

Studio 6 Fishkill|King bed|Hearing Access|Kitchen

Studio 6 Fishkill|King bed|Hearing Access|Kitchen
Fishkill
10.0 out of 10, Exceptional, (18 reviews)
"great place to stay"
United States
Anonymous traveler
$103 nightly
The price is $119
Jun 17 - Jun 18
Total with taxes and fees
Studio 6 Fishkill|King bed|Hearing Access|Kitchen

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, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$479 nightly
The price is $528
May 26 - May 27
Total with taxes and fees
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

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, (138 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
$277 nightly
The price is $327
May 25 - May 26
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (20 reviews)
"Very good communication and helpful. "
United States
Liam C.
$296 nightly
The price is $303
May 26 - May 27
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

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, (13 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
$389 nightly
The price is $422
May 25 - May 26
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (6 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
$368 nightly
The price is $421
May 26 - May 27
Total with taxes and fees
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
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

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 $126 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.

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.

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.