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Brewster Vacation Rentals

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Our top choices for Brewster vacation rentals

The Tipsy Gypsy - Studio Apartment

The Tipsy Gypsy - Studio Apartment
Brewster
The price is CA $212
CA $393 total
includes taxes & fees
Jun 28 - Jun 29
The Tipsy Gypsy - Studio Apartment

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (9 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is CA $177
CA $555 total
includes taxes & fees
Jun 21 - Jun 22
House on the Babbling Brook- Quiet 2BR + King Bed!

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.
The price is CA $156
CA $290 total
includes taxes & fees
Jun 22 - Jun 23
Hoppy Hill Farm House

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, (8 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.
The price is CA $113
CA $189 total
includes taxes & fees
Jul 1 - Jul 2
Rare, peaceful glamping, hot shower, mini golf near appalachian trail

2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.8 out of 10, Exceptional, (19 reviews)
"great place tostay"
United States
Anonymous traveller
The price is CA $156
CA $180 total
includes taxes & fees
Jun 28 - Jun 29
2 Full Beds | Non-Smoking, Kitchen

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 traveller
The price is CA $127
CA $144 total
includes taxes & fees
Jul 12 - Jul 13
1 King Bed | Non-Smoking, Kitchen, Shower

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, (139 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
The price is CA $280
CA $471 total
includes taxes & fees
Jun 23 - Jun 24
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
The price is CA $149
CA $282 total
includes taxes & fees
Jun 23 - Jun 24
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Beacon
10.0 out of 10, Exceptional, (58 reviews)
"Great location and quiet just like we like it. Unit was very charming."
Canada
Thomas
The price is CA $170
CA $360 total
includes taxes & fees
Jul 1 - Jul 2
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

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, (53 reviews)
"Have stayed a few times now… absolutely wonderful!! Clean, cozy, and comfortable! "
United States
Daniela C.
The price is CA $163
CA $345 total
includes taxes & fees
Jun 23 - Jun 24
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, 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
The price is CA $191
CA $393 total
includes taxes & fees
Jun 21 - Jun 22
Charming 1-bedroom apartment in Carmel with WiFi, AC

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (34 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is CA $318
CA $599 total
includes taxes & fees
Jun 21 - Jun 22
Contemporary Cozy Cottage

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, (14 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is CA $318
CA $603 total
includes taxes & fees
Jun 21 - Jun 22
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.0 out of 10, Very good, (6 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is CA $212
CA $693 total
includes taxes & fees
Jun 23 - Jun 24
3BR West Point Retreat-3min to Back Gate+ King Bed

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 CA $206
CA $328 total
includes taxes & fees
Jun 21 - Jun 22
The Perch in the Purchase -- Cozy, unique, and private

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is CA $230
CA $391 total
includes taxes & fees
Jul 21 - Jul 22
Cozy 1-bedroom retreat minutes from West Point!

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 CA $280
CA $380 total
includes taxes & fees
Jun 23 - Jun 24
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (15 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is CA $235
CA $301 total
includes taxes & fees
Jun 22 - Jun 23
Mid Century Modern Studio w/ Full Kitchen - Newly Built

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (17 reviews)
"Sweet abode. Cozy, clean and amazing location. The cute coffee bar was a nice bonus. Would definitely stay there again. "
United States
Danica J.
The price is CA $195
CA $636 total
includes taxes & fees
Jun 23 - Jun 24
Local Artist Inspired | Walk to WestPoint + King Bed

Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (3 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is CA $428
CA $651 total
includes taxes & fees
Jul 13 - Jul 14
Rustic Cabin in Fishkill!
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Brewster. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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 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.