Brewster Vacation Rentals

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Vacation Rentals in Brewster

Property grounds
The Hideaway
10.0 out of 10, Exceptional, (1)
"We enjoyed our short stay with Renee, who was very helpful! Plenty of room for our XL dogs to walk - ( 90lbs and 188lbs). Thank you for your hospitality! We’ll see you again, if we’re in the area!"
The price is CA $191
CA $374 total
includes taxes & fees
May 19 - May 20
The Hideaway
Fridge, microwave, oven, stovetop
Adorable 1-Bedroom Cottage in Weston, CT
10.0 out of 10, Exceptional, (24)
"Clean, Safe, and Comfortable! Thank you Jacques for the convenience of staying near Westport !"
The price is CA $266
CA $412 total
includes taxes & fees
May 19 - May 20
Adorable 1-Bedroom Cottage in Weston, CT
Game room
Peaceful apartment on 3.5 acres w/ artist studio.
10.0 out of 10, Exceptional, (11)
"Cute."
The price is CA $190
CA $289 total
includes taxes & fees
Jun 9 - Jun 10
Peaceful apartment on 3.5 acres w/ artist studio.
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Property grounds
Lake Luxury
10.0 out of 10, Exceptional, (8)
"We loved our stay at this home. Plenty of space so we didn’t feel like we were on top of each other, gorgeous kitchen (plus a separate butler’s kitchen!), and lux bathrooms made this rental exactly what we needed. Thanks Gianna!"
Lake Luxury
Property grounds
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
10.0 out of 10, Exceptional, (15)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Smart TV, fireplace
The Long View of Candlewood Lake
10.0 out of 10, Exceptional, (6)
"It was such a nice property and the host was amazing"
The Long View of Candlewood Lake
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (15)
"We so enjoyed our stay! The house was perfect for our family, conveniently located close to extended family and with the most beautiful view. The house had everything we needed and provided the perfect home base for spring break in our hometown. We even got to experience an earth quake ;) thank you!!"
Serenity Awaits at this Cozy Lakeside Bungalow
Property grounds
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, (6)
"This house was exactly as advertised and very charming. The owners were very easy to work with. We had a beautiful view of the lake from the porch. We would stay here again."
Candlewood Lake Retreat with year round views
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (61)
"The property and house were beautiful, out of the way but beautiful. The fire pit, sunroom, and porch were amazing. It was great for decompressing after a West Point graduation. Thank you for sharing your little piece of heaven."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Outdoor pool
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (17)
"This house is located minutes from the highway making it easy to get to. Its a very scenic and country area so you feel farther away then you are. The house is extremely clean and well appointed it sits up high on a hill so you can enjoy the veiw of the country house across the street which has a small creek and gardens to enjoy theres even a pool to enjoy in summer months and a fire pit .this house was peaceful and perfect for the quick weekend getaway that we all needed. The host Pat was...
The price is CA $214
CA $405 total
includes taxes & fees
May 28 - May 29
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Property grounds
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
10.0 out of 10, Exceptional, (16)
"From the moment we came we felt right at home! Such a comfortable place to stay! Every morning we were greeted by a beautiful bald eagle on the lake as well as the chitter chatter of birds. For those who have a hard time climbing stairs, this is NOT the place for you. Bedrooms as well as bathrooms are not on the main level. No matter we would definitely want to stay again!"
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Outdoor dining
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (17)
"We had a wonderful stay in the house. It has incredible views and the lake is beautiful."
The price is CA $633
CA $1,287 total
includes taxes & fees
May 23 - May 24
Lakeview Estate - Chef's Kitchen - NYC Getaway
Property grounds
Lakefront New York Abode w/ Deck, Grill & Fire Pit
10.0 out of 10, Exceptional, (3)
"Clean, spacious, and many activities in a nice quiet town. The house comfortably fit our 10 people."
Lakefront New York Abode w/ Deck, Grill & Fire Pit
Fireplace
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (1)
"A very short but pleasant stay and the host gave us good communication."
The price is CA $340
CA $513 total
includes taxes & fees
May 20 - May 21
Contemporary Cozy Cottage
Outdoor pool, a heated pool
Westport Paradise With Every Amenity!
10.0 out of 10, Exceptional, (12)
"Super clean, comfortable, and great for overnight stay. Will definitely be back!"
The price is CA $761
CA $1,098 total
includes taxes & fees
May 20 - May 21
Westport Paradise With Every Amenity!
Property grounds
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
10.0 out of 10, Exceptional, (5)
"This was a great location. Only changes I would make is a light under the eagle to find it better at night and to update the listing with the new photo of house with the blue paint."
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
Exterior
Traveling Nurse or Business Professional
10.0 out of 10, Exceptional, (7)
"The neighborhood was clean, upscale, and beautifully kept. It came with Candlewood Beach access. The second story suite was gorgeous, clean, and well apportioned. The bed was comfortable. The whole house was well maintained and a wonderful,"homey" feel to it. The Hostess was friendly, cheerful, and very accommodating. The house is on the hillside leading to Lake Candlewood. As can be imagined, the views from the windows were outstanding."
Traveling Nurse or Business Professional
1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Property grounds
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is CA $251
CA $361 total
includes taxes & fees
May 20 - May 21
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Don't see what you're looking for?
See all available properties in Brewster
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.

Other types of properties in Brewster you may be interested in

Lobby
Comfort Inn
2.5 star property
8.8 out of 10, Excellent, (299)
"Our refrigerator is not working luckily we booked two rooms and stored our refrigerated items there. We have not let management know, but will notify them in the morning. Good night."
The price is CA $184
CA $199 total
includes taxes & fees
May 20 - May 21
Comfort Inn
Seasonal outdoor pool, free cabanas, pool umbrellas
Heidi's Inn
2.5 star property
8.6 out of 10, Excellent, (576)
"Friendly "
The price is CA $171
CA $185 total
includes taxes & fees
May 23 - May 24
Heidi's Inn
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
HYATT house Fishkill/Poughkeepsie
3.0 star property
8.6 out of 10, Excellent, (1000)
"Great"
The price is CA $193
CA $216 total
includes taxes & fees
May 28 - May 29
HYATT house Fishkill/Poughkeepsie
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.

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Brewster vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Brewster vacation rentals we have selected for you start as low as CA $190 per night. Entering your travel dates in the search wizard 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.

What's the top vacation rental that Brewster has to offer?

Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond: This vacation home rental outside of Brewster is located on the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a spa tub.

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 Kouros Sculpture Center, or visit a family-friendly sight such as SplashDown Beach. Brewster Public Library and Centennial Golf Club are a couple of places you'll find in the larger area.

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.

Recent reviews of Brewster properties
Expedia verified reviews