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Featured Cottages in Brewster

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (99)
"Wonderful hilltop location. Beautiful view. Nice apartment. Great hosts. Wish we could have stayed longer! "
The price is NZ$405
includes taxes & fees
1 Oct - 2 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Putnam Valley Vacation Rental: Patio & Lake Views!
9.6 out of 10, Exceptional, (10)
"The home is beautiful and spotless! View was spectacular! We really enjoyed our time there, thank you!"
Putnam Valley Vacation Rental: Patio & Lake Views!
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
9.4 out of 10, Exceptional, (82)
"Property was clean, well appointed, wish we could have stayed a bit longer to enjoy more of the lake & fire pit! "
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Charming tiny home in delightful Beacon, 2 blocks from main st. Private patio
9.8 out of 10, Exceptional, (8)
"This adorable tiny home was a perfect fit for our visit to Beacon. New and nicely decorated, it had everything we could need. The shower is a "show-stopper"! Very short walking distance to Main Street, coffee shops, restaurants and a grocery store. Very pleased with our stay!"
Charming tiny home in delightful Beacon, 2 blocks from main st. Private patio
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
10.0 out of 10, Exceptional, (1)
"Great relaxing stay quite and comfortable "
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
10.0 out of 10, Exceptional, (2)
"Highly recommend. We visited the River Cottage on our Anniversary trip to Connecticut! The cottage is quaint, relaxing and peaceful. The location is beautiful and convenient to hiking, parks, dining and shopping. The hosts are kind, respectful and welcoming! We cannot wait to stay here again. "
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Adorable 1-Bedroom Cottage in Weston, CT
10.0 out of 10, Exceptional, (30)
"Very cozy cottage a little off the beaten path in Weston. Quiet & stocked with amenities for our comfort. The owner was helpful & responsive. If there was any drawback it would be helpful to air out the cottage as its an old building & investing in some new pillows would be appreciated by the next guests. Otherwise a great stay."
The price is NZ$481
includes taxes & fees
30 Sept - 1 Oct
Adorable 1-Bedroom Cottage in Weston, CT
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
9.6 out of 10, Exceptional, (14)
"Landscaping was spectacular and we enjoyed a beautiful view of the lake. Baths and bedrooms very clean. Plenty of charging ports. Terrible mold and mildew smell in lower level. Number of hazards noted, handrail missing on stairs, no lights on outdoor stairway, thermostat access by leaning over the stairs. The property needs a good deep cleaning."
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
10.0 out of 10, Exceptional, (5)
"Lovely little cottage right on the arm of the lake. Nicely appointed and updated, quiet and great for a couple. Nearby towns are adorable."
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Putnam Valley Vacation Rental: Patio & Lake Views!
3.0 star property
Putnam Valley Vacation Rental: Patio & Lake Views!
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, (10)
"Liked outdoor area and fire place "
Candlewood Lake Retreat with year round views
Charming Private and Serene cottage close to I-84 and shopping
The price is NZ$720
includes taxes & fees
16 Oct - 17 Oct
Charming Private and Serene cottage close to I-84 and shopping
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
9.4 out of 10, Exceptional, (3)
"I spent 2 serene weeks here and hope to return some day! With modern creature comforts in the kitchen, the rest of this home is very rustic. If you are looking for peace and quiet, and are into drawing, cooking or reading books to the sounds of trees rustling and water flowing across the street, you will be in heaven here. For summer months, note that there is only a small portable AC unit in the sunroom. There are several fans and it was manageable in early summer, but I imagine it is quite...
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Cottage Getaway DogFriendly, Grill, Walk to Lake
10.0 out of 10, Exceptional, (14)
"My husband and I were very happy with our stay here. Sara was a communicative and flexible host, even before we arrived. The place matched our expectations from the listing. The cottage was clean, comfortable and had everything we needed for our multiple day stay. "
The price is NZ$648
includes taxes & fees
22 Oct - 23 Oct
Cottage Getaway DogFriendly, Grill, Walk to Lake
Beautiful Cottage in Hudson Valley w/Pool & Views
9.8 out of 10, Exceptional, (9)
"We enjoyed our stay with friends very much and found the home to be very accommodating. Our only disappointment was that there was no hot tub. The indoor bathtub should not be considered one."
The price is NZ$1,103
includes taxes & fees
1 Oct - 2 Oct
Beautiful Cottage in Hudson Valley w/Pool & Views
Dreamy Hudson Valley Cottage w/ State Park Views
9.6 out of 10, Exceptional, (9)
"Very clean and modern home, surrounded by woods. 15-30 minute drive from amazing hikes, lakes and cultural events. Hosts were very responsive and left nice little touches like snacks and bug spray! Would definitely stay there again."
Dreamy Hudson Valley Cottage w/ State Park Views
Dainty New Preston Cottage w/ Dock & Lake Views!
9.0 out of 10, Wonderful, (33)
"We were in need of a nice, relaxing vacation and that’s exactly what we got. There were four of us (me, my husband, my 16-year-old, and my 11-year-old) and we each had our own space. We loved going down to the dock, and there is also a town beach just down the road. The home is filled with fun antiques and reminds you of a clean, well-kept, and charming grandmother’s house. We wanted a low-key vacation, and so we enjoyed short jaunts (less than 15 mins away) to Kent to enjoy its downtown and...
Dainty New Preston Cottage w/ Dock & Lake Views!
Lakefront Brewster Vacation Rental w/ Private Dock
10.0 out of 10, Exceptional, (3)
"Family trip consisting of 2 grandparents, 2 parents, and 1 adult grandchild went off without a hitch. The property is so beautiful- meticulously clean house, soft beds and luxury bedding, top notch kitchen appliances, with the most peaceful view of the lake. Excellent communication from host, including helpful welcome book. Fresh loaf of cranberry bread from local farmer’s market was a nice touch. DeCicco’s Market was our go-to for groceries / wish we had one of those at home. Enjoyed...
Lakefront Brewster Vacation Rental w/ Private Dock
Dreamy Hudson Valley Cottage w/ State Park Views
3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was amazing with great amenities. The kitchen was stocked with all the utensils and cutlery. The patio was a good addition. Overall great stay! "
Dreamy Hudson Valley Cottage w/ State Park Views
South Salem Vacation Rental w/ Furnished Deck!
10.0 out of 10, Exceptional, (1)
"Everything was easy and fine at the space. I had to stay for family reasons - so "location" was the most important factor to me. The worst thing in the unit is that the spiral stair is narrow - and a fat person or person with bad knees is NOT going to be using that stairwell easily. Otherwise, the unit had everything I needed and was perfectly appointed for an easy weekend stay. Enjoy!"
South Salem Vacation Rental w/ Furnished Deck!
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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, (2)
"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 NZ$435
includes taxes & fees
29 Sept - 30 Sept
The Hideaway
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (99)
"Wonderful hilltop location. Beautiful view. Nice apartment. Great hosts. Wish we could have stayed longer! "
The price is NZ$405
includes taxes & fees
1 Oct - 2 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (64)
"The good: We had a great time staying here. The first and second floor are beautiful and very well maintained. Both bathrooms and three bedrooms are very clean and have more than enough bath and beach towels. The fire pit and kayaks are also a great touch. The water is just steps away and the view is excellent. Just be sure to bring your own propane and firewood. What could be better? Communication with the host left a lot to be desired. I’m still not sure who runs the property. There are two...
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
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.

Frequently asked questions

What is there to do in Brewster near my cottage?
The most practical travel accessory is a well-thought-out travel plan. Brewster Public Library is a top place to start your exploration of Brewster.