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Compare 332 Vacation Homes in Brewster with updated reviews, rates, and availability.

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

9.4 out of 10, Exceptional, (3)
"Plenty of room for my family"
The price is SAR 972
SAR 1,107 total
includes taxes & fees
22 Mar - 23 Mar
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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

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.

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

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

9.4 out of 10, Exceptional, (9)
"We stayed here for work event and the location was perfect. Not too close, not too far away. Its snowed one evening but the driveway was not slippery at all. The house was very clean and kept in order. Plenty of room in the bedrooms and bathroom. The operational fireplace was also an added bonus. "
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (95)
"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!

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (16)
"It was a quick trip to see woman’s army basketball game. It was an excellent stay and excellent accommodations. "
The price is SAR 938
SAR 1,399 total
includes taxes & fees
27 Mar - 28 Mar
Contemporary Cozy Cottage

Modern home w/creek view, steps to town & mountain

Modern home w/creek view, steps to town & mountain

Modern Farmhouse Walking Distance to West Point

9.2 out of 10, Wonderful, (7)
"A second stay at this home. The location truly can't be beat at this cozy historic home. The home has lots of charm from the wood floors, to the covered front porch, to the nice backyard. Restaurants and Pubs are a quick walk, a wine store is a few paces away for that relaxing end-of-night glass. I previously reviewed the place and noted a lack of a baking sheet (as did a prior reviewer). We purchased one for the kitchen on our stay as well as a stock pot - cold night air called for a pot...
Modern Farmhouse Walking Distance to West Point

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (18)
"We had a friend group boardgaming weekend and this was perfect for our purposes. The table was large enough for our biggest games and the pool table doubled as a backup playing space. The race cars are a nice touch of whimsy too :-) Our only suggestion would be to replace the oversized, too-low chandelier over the table but really only a minor thing."
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown

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

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

NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

10.0 out of 10, Exceptional, (5)
"This place is amazing!! The house had everything we needed and more. We really enjoyed our stay and also be able to host some of our family in the area was precious. My daughters rented equipment for the babies which worked out well. The house is very spacious and 5 adults and 3 children fit nicely. Very highly recommend. The pier was fun to hang out on but due to weather we were to enjoy the lake as much. Easy to find, and owners were very responsive. "
NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

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

Have a quiet weekend retreat at my recently renovated riverside bungalow

Have a quiet weekend retreat at my recently renovated riverside bungalow

Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants

10.0 out of 10, Exceptional, (39)
"Excellent stay in s as wonderful house. "
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants

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

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (41)
"This house is fantastic in every way. The space is spacious, comfortable, and beautifully appointed. Kerry was super communicative, extremely professional and so nice.. The house was filled with unexpected amenities and the views are spectacular. This was the perfect spot for the 6 of us. "
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

10.0 out of 10, Exceptional, (38)
"Review of VRBO Home - Our Rockbound Highland Rating: ⭐⭐⭐⭐⭐ (5/5) - Exceeded Expectations I recently stayed at a VRBO home that completely surpassed my expectations! The home was not only beautiful but incredibly comfortable, offering all the amenities promised in the listing. It felt like a home away from home and matched the online photos perfectly, which made our stay even more enjoyable. The check-in process was seamless, and the communication with the property manager was top-notch. This...
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.
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 1,043 total
includes taxes & fees
23 Mar - 24 Mar
The Hideaway

Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT

8.8 out of 10, Excellent, (5)
"Truly a gem of a place! We loved it. Great spot to celebrate my 30th birthday with a low-key, mellow group. My chef friend who cooked the entire weekend was thrilled at the industrial-style kitchen. The house is probably unlike anything you've ever seen. We're still talking about it haha. A lovely spot. "
The price is SAR 2,795
SAR 4,909 total
includes taxes & fees
6 Apr - 7 Apr
Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT

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

9.4 out of 10, Exceptional, (3)
"Plenty of room for my family"
The price is SAR 972
SAR 1,107 total
includes taxes & fees
22 Mar - 23 Mar
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
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.