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Compare 341 Vacation Homes in Brewster with updated reviews, rates, and availability.

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.6 out of 10, Exceptional, (5)
"Plenty of room for my family"
The price is SAR 972
SAR 1,107 total
includes taxes & fees
1 Apr - 2 Apr
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (6)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.2 out of 10, Wonderful, (33)
"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."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

10.0 out of 10, Exceptional, (106)
"The title says it all really. The house is as well equipped as your home, superbly comfortable, has glorious views East over the lake, has space for everyone and was just a delight to stay in. Lisa is so repsonsive, thoughtful and kind, which just adds to the warmth of feeling and quality of experience. Thank you very much indeed. "
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

9.8 out of 10, Exceptional, (28)
"Our family's stay at Helen and Richie's property for the holidays was perfect. Waking up to views of the lake every morning, watching flocks of birds travel on the water and being surrounded by nature was all we could ask for. The house has all amenities provided in the kitchen, bathrooms etc. Location is convenient near shops, grocery, and restaurants in New Fairfield. The hosts were very responsive in communication and I appreciated them providing everything we needed. "
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (96)
"House is absolutely perfect! This is our second time staying and we will definitely return. So much charm and warmth. I had the best sleep that I have had in months. All the amenities you could ask for, and more. Terrific convenient location. Host goes above and beyond to make sure we are comfortable. "
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Pet-Friendly Beacon Area Vacation Rental: 6 Acres

10.0 out of 10, Exceptional, (12)
"Great place to stay for all ages. Had everything we needed and lots of room to relax. Definitely will stay here again next time we come. Comfy beds, easy to get to, easy check in, everything we needed in the kitchen, lots of books and toys, great outdoor space. Thanks for providing the perfect place to stay with extended family! "
Pet-Friendly Beacon Area Vacation Rental: 6 Acres

Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (16)
"This is a fully decked out house with cozy beds, full kitchen, completely up to date amenities. The host is very accessible, polite, and helpful."
The price is SAR 938
SAR 1,399 total
includes taxes & fees
9 Apr - 10 Apr
Contemporary Cozy Cottage

Modern, Magical Woodsy Escape 1 Hour From NYC

10.0 out of 10, Exceptional, (22)
"The home was beautiful, comfortable and so spacious. Great time with friends made even better by the location. The amenities were great, beds were so comfortable and quality toiletries provided. Would definitely considering coming back. Not one complaint. Host set us up to have a winderful weekend. "
Modern, Magical Woodsy Escape 1 Hour From NYC

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (39)
"The home was spacious and provided recreation for kids with hot tub, gym, ping pong, foosball, and game. However, property was advertised as 9 bedrooms and 7 baths. My family looked forward to spreading out but 4 bedrooms with adjoining bathrooms were locked. Text host to see if he would open them but he declined. That was disappointing."
Over Sized Colonial on Private Road.

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.4 out of 10, Exceptional, (10)
"I was pleasantly surprised! The house looked even better in person than it did in the photos. It is warm and comfortable and they had everything we needed to enjoy our time away. The house was clean and the surrounding property was well maintained. I would love to come back in the spring/summer to enjoy more of the outdoors. "
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lovely 3BR Home with parking-Walk to WP Gate!

10.0 out of 10, Exceptional, (2)
"Close to west point where we were able to attend the sporting event. It is walking distance to the small town outside campus where you can find local shops for eating or shopping. ."
The price is SAR 658
SAR 1,066 total
includes taxes & fees
1 Apr - 2 Apr
Lovely 3BR Home with parking-Walk to WP Gate!

Cottage at Sunny Day- Lakeside, views, kayak, dock

9.8 out of 10, Exceptional, (35)
"This property was very new and clean. It had everything you needed. Every room was comfortable and had its own TV. The open layout of the main floor made for great socializing and eating, and the 180 views of the frozen lake (in February) were beautifully serene. Would definitely come again and maybe next time in the summer! Thanks you for sharing this lovely property."
Cottage at Sunny Day- Lakeside, views, kayak, dock

Waterfront Family Retreat on Candlewood Lake

10.0 out of 10, Exceptional, (41)
"The Hosts were extremely nice and helpful in the entire process. They answered questions and helped me understand the offering so I could book with confidence, The home is spacious and welcoming in design. Generous spaces throughout including a very nice kitchen and a basement gameroom that was very enjoyable. The outside seating areas were outstanding including a wonderful lakefront area to sit and enjoy the views. Book with confidence for a great experience. Dan and Kit "
Waterfront Family Retreat on Candlewood Lake

Litchfield County Four Season Country Paradise

9.6 out of 10, Exceptional, (40)
"Considering that area does not have convenient hotels, this location was perfect for the event we attended. It was nice of them to vacate their home so we could stay - though we wish that would have been communicated. There is no extra room with twin beds - at least not functional. The property is nice. Whomever took the pictures did a great job. It worked for us for the short time we were in the area."
Litchfield County Four Season Country Paradise

Charming Hudson Valley 3-Bedroom Family Getaway

8.0 out of 10, Very Good, (2)
"Nice entryway, lots of room for shoes. 1st and 3rd floor bedrooms were spacious. Nice size livingroom. Need more cookware for kitchen, and would recommend fixing the exhaust fan in the bathroom, and a better foundation for the attic bed. Moving slats caused the mattress to sag, especially at the foot of the bed. We would stay again. "
The price is SAR 614
SAR 1,069 total
includes taxes & fees
6 Apr - 7 Apr
Charming Hudson Valley 3-Bedroom Family Getaway

Westport Gem - walk to shops, dining, town center, pet-friendly

10.0 out of 10, Exceptional, (3)
"After a rough year we were able to get a few days away and at the last minute chose this location. Everything we were looking for was there. The home and grounds were beautiful. The location in Westport was exactly what we wanted: magnificent fall foliage, quiet where the home was but close enough to walk to town and enjoy every aspect of being close by the town for lovely cafes and restaurants. Also, beautiful places were accessible by car in minutes such as Earthplace for trails and nature...
Westport Gem - walk to shops, dining, town center, pet-friendly

19 Mi to Thunder Ridge Ski Area: Home w/ Fire Pit

9.2 out of 10, Wonderful, (13)
"We had a great time at the cabin. It was well appointed and very clean. Beautiful kitchen and bathrooms. And, the grounds were lovely. "
19 Mi to Thunder Ridge Ski Area: Home w/ Fire Pit

Have a quiet weekend retreat at my recently renovated riverside bungalow

Have a quiet weekend retreat at my recently renovated riverside bungalow
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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Other property types in Brewster

The Hideaway

10.0 out of 10, Exceptional, (4)
"Me and my family stayed here for a quick get-away out of the city. Very pretty location, and loved our stay here! Thanks!"
The price is SAR 544
SAR 1,047 total
includes taxes & fees
2 Apr - 3 Apr
The Hideaway

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.6 out of 10, Exceptional, (5)
"Plenty of room for my family"
The price is SAR 972
SAR 1,107 total
includes taxes & fees
1 Apr - 2 Apr
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (108)
"Awesome "
The price is SAR 690
SAR 998 total
includes taxes & fees
28 Apr - 29 Apr
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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.