Brewster Vacation Rentals

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Vacation Rentals in Brewster

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (122)
"It has an incredible mountain and water view. "
MIHYUN
$272 nightly
The price is $308
Oct 22 - Oct 23
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.8 out of 10, Exceptional, (41)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
Lisa B.
$296 nightly
The price is $335
Nov 1 - Nov 2
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
10.0 out of 10, Exceptional, (195)
"Wonderful place to rest and recharge."
Clair T.
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (42)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
Uros K.
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
9.8 out of 10, Exceptional, (11)
"Easy check in and check out! Has all the bare minimums and a nicely upgraded bathroom. Didn’t feel super clean (the bathroom) when we got there but kitchen was clean and they kindly stocked a few groceries. Could not get the water hot for a shower which was bummer. Nice enough depending on what you are looking for! We had some sensory needs and so this ended up not being the best fit but the location was great. Thanks for having us. "
Laura
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
9.4 out of 10, Exceptional, (30)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Anonymous traveler
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
10.0 out of 10, Exceptional, (2)
"This is a property that is very good for large family gatherings, which is how we gathered for a birthday celebration. This area of CT. is great and has lots to do.The house is in the perfect location to do all of it.Again, suits large groups well. Room for everyone."
Paula R.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Chestnut on Willow Lake
9.4 out of 10, Exceptional, (3)
"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."
Doria W.
$511 nightly
The price is $582
Oct 20 - Oct 21
Total with taxes and fees
Chestnut on Willow Lake
Hickory on Willow Lake
9.6 out of 10, Exceptional, (4)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
Rachel C.
$539 nightly
The price is $614
Oct 20 - Oct 21
Total with taxes and fees
Hickory on Willow Lake
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (91)
"My family and I loved this property! We enjoyed walking around the woods and exploring. The house was well equipped and was really charming. We also loved sightseeing around the near by towns. Definitely a place to come back to stay again. "
Hector L.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
8.8 out of 10, Excellent, (5)
"We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. "
Matthew W.
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Rustic Cabin in Fishkill!
10.0 out of 10, Exceptional, (2)
"The place was very nice, we met the owner and he was also bery accommodating. This is definitely a family friendly spot. "
Arron T.
$318 nightly
The price is $361
Nov 1 - Nov 2
Total with taxes and fees
Rustic Cabin in Fishkill!
price will make you book twice , luxury living
10.0 out of 10, Exceptional, (1)
"We had a great stay! Room was very open and clean and our host was friendly and welcoming! "
Sage
$146 nightly
The price is $165
Oct 23 - Oct 24
Total with taxes and fees
price will make you book twice , luxury living
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
3.0 star property
10.0 out of 10, Exceptional, (2)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
Varuna S.
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
7 BR Mansion , Celebration Welcomes
10.0 out of 10, Exceptional, (1)
"I had a wonderful stay at this house. It was very clean, comfortable, and beautifully maintained.Everything was exactly as described, and I really appreciated the welcoming atmosphere. Even though I only stayed for one day, it was an amazing experience. I would definitely recommend this place and would love to stay again in the future."
Mikado B.
$799 nightly
The price is $904
Oct 27 - Oct 28
Total with taxes and fees
7 BR Mansion , Celebration Welcomes
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
10.0 out of 10, Exceptional, (13)
"The house worked very well for our family holiday. Very clean, had everything we needed "
Audrey P.
$491 nightly
The price is $556
Oct 22 - Oct 23
Total with taxes and fees
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
Peaceful Vintage Home with Private Lake in Redding, CT.
2.0 star property
10.0 out of 10, Exceptional, (1)
"Several of us stayed for one night for our kids soccer tournament. The home was spacious and had all the amenities needed to make our short stay comfortable. The host was very responsive and accommodating. "
Annette H.
$668 nightly
The price is $757
Oct 20 - Oct 21
Total with taxes and fees
Peaceful Vintage Home with Private Lake in Redding, CT.
Charming 1-bedroom apartment in Carmel with WiFi, AC
10.0 out of 10, Exceptional, (1)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
Emmett
$217 nightly
The price is $235
Oct 31 - Nov 1
Total with taxes and fees
Charming 1-bedroom apartment in Carmel with WiFi, AC
2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!
10.0 out of 10, Exceptional, (7)
"This condo is located very close to the Garrison train station. It has been designed so that you are never disturbed by the sound of the trains. Really soundproof! There is a beautiful view of West Point across the Hudson River from the balcony and other windows. The kitchen and 2 1/2 bathrooms are modern and well equipped. Matt, the host, has thought of everything when it comes to making his guests feel comfort and st home. The beds were extra comfy and both bedrooms were quite spacious....
Eileen S.
2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (28)
"Very clean comfortable quiet place"
Mauro C.
$369 nightly
The price is $422
Oct 19 - Oct 20
Total with taxes and fees
Contemporary Cozy Cottage
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 $165 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.

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental outside of Brewster offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and kitchenware, 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 4 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.