Vacation rentals in Brewster

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Quick stats about vacation rentals in Brewster

Nightly prices starting at
Brewster vacation rentals start at R 1,310 ZAR per night before taxes and fees
Verified guest reviews
Over 140 verified reviews to help you choose
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Brewster rentals
4.8 Average rating
Brewster stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Brewster

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A dining area is shown with a round wooden table at the center, adorned with a vase of flowers. Large glass windows frame a serene lakeside view, with blooming flowers in the foreground and lush greenery. Soft sunlight reflects off the water, creating a tranquil atmosphere.

Home in Carmel Hamlet

Lux Bungalow on the Lake

Beautiful, light flooded, waterfront home 1 hour from New York City. The 2 bedroom home is on picturesque Lake Carmel. Wake up, eat, sleep and relax to the tranquil view of the glistening water - truly an oasis! Take in a sunset while eating a meal at home, explore the shops and restaurants in a cute nearby town, take a walk around the lake, read a book by the cozy fireplace, hike, cook, kayak, ski, or just sit and enjoy. Centrally located close to Hudson Valley, Westchester and Connecticut.

4.93 out of 5 average rating, 231 reviews

Top guest favorite

Apartment in Holmes

Top Side

Welcome to Top Side! Nestled in Holmes, NY, Top Side offers lovely views of Whaley Lake. Whether you're looking for a relaxing getaway or an adventure, you'll find plenty of reasons to fall in love with this spacious apartment which is designed to help you unwind and recharge. The Hudson Valley is brimming with activities and attractions for everyone. From historic landmarks and charming villages to outdoor adventures and local dining, you're never far from something special to experience.

5.0 out of 5 average rating, 150 reviews

Top guest favorite

A rustic black barn is showcased, featuring wooden doors and exterior lighting. A paved driveway leads up to the entrance, bordered by a well-maintained lawn and trees. The surrounding natural landscape enhances the barn's secluded charm.

Guesthouse in Brewster

Sherwood Barn - close to ski mountain

Our guests stay on the SECOND floor of the barn in a 1200 Sq Ft, fully reno'd apt that sleeps 6. Located about 1 hour from NYC you will find peace and serenity in the middle of nature on this 4 acre estate (that also contains our main home) where you can get away from it all. unwind this way or visit local attractions like Thunder Ridge Ski Mountain, snowshoe/ X Country skiing, hike/bike/running trails, restaurants and local cafe's. Great oasis to kick back and spend time with family.

4.95 out of 5 average rating, 193 reviews

Guest favorite

The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.

Guesthouse in Waccabuc

French Estate Guest House on Private Lake

A private, European-inspired guest house set on an eight-acre gated French estate, just 60 minutes from NYC. Surrounded by manicured gardens, 18th-century statuary, and a private lake, the setting feels transportive—a French countryside retreat. Designed by architect David Easton, the space blends classic elegance with modern comfort: heated stone floors, a heated towel rack, fine linens, curated finishes, and a private entrance. Perfect for a refined weekend escape or a quiet reset.

4.99 out of 5 average rating, 150 reviews

Guest favorite

An outdoor seating area is featured with two ornate egg chairs and a spacious sofa. The furniture is complemented by colorful cushions, and a geometric patterned rug is placed underneath. A stone fireplace is visible in the background, surrounded by trees.

Home in New Fairfield

Hilltop Retreat- Lakefront with Dock

Enjoy all that Candlewood Lake and Squantz Pond State Park have to offer in the comfort of our home. Come reconnect with love ones and relax in the serene surroundings. This waterfront property has a private dock, features 2 bedrooms, 2 full baths, and views from almost every room in the home, plenty of indoor and outdoor entertaining space and a wood burning fireplaces to keep toasty during chilly evenings. Toiletries, all linens are provided. Please read house rules before booking.

4.95 out of 5 average rating, 105 reviews

Top guest favorite

The outdoor area features a grassy lawn surrounded by trees, with a rustic wooden table and chairs set for gathering. A stone pathway leads through the yard, where small trees and decorative birdhouses add charm to the tranquil natural setting.

Cabin in Carmel Hamlet

Peaceful Forest Cabin

Nestled down a quiet dirt road, this authentic, rustic 1800s log cabin has been lovingly updated with timeless style and all-new appliances in 2023. Perfectly situated on 4 private acres with native and perennial pollinator meadows! Lower Hudson Valley and surrounded by over 1,000 acres of State Forest, it's easy to stay in and bathe in nature, read a book, and bird-watch. Or, there’s easy access to hiking, shopping, and dining in nearby Katonah, Cold Spring, Beacon, Hudson, or NYC!

4.94 out of 5 average rating, 112 reviews

Top guest favorite

Home in Newtown

Comfortable home away from home- near everything

Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

4.99 out of 5 average rating, 148 reviews

Top guest favorite

A tranquil lakeside scene at sunset features vibrant pink and orange hues reflected on the calm water. Silhouetted trees line the shore, and rolling mountains rise in the distance, creating a serene backdrop.

Cottage in South Salem

Serene lake front cottage 1 hour from NYC

Serene minimalist cottage directly on Lake Oscaleta with spectacular waterfront and Mountain Lakes Park behind. Quiet, isolated and lost in the trees, you feel you are in Vermont or the Adirondacks. Yet it's only 1 hour from Manhattan, 10 minutes from restaurants. Kayak, canoe, fish, paddleboard. Cottage is elegant, cozy and winterized warm and the lake is effectively empty in the fall/winter/spring. Please note: because of an asthmatic child, we cannot accept any animals.

4.97 out of 5 average rating, 149 reviews

Top guest favorite

A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.

Cabin in Sherman

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two two-person kayaks are available for use from May 1 to November 1.

4.96 out of 5 average rating, 463 reviews

Guest favorite

An open living space features high cathedral ceilings and warm wood flooring. A sleek sectional sofa is positioned around a glass coffee table. A staircase with wooden railings leads to an upper level, while a cozy fireplace is situated next to a television mounted on the brick wall.

Home in Mahopac

Peaceful & Spacious Retreat

Big and beautiful house fully renovated in 2020 sitting on half an acre of land in Mahopac. Open floor concept with high cathedral ceilings in living space. Kitchen fully stocked with everything you need to cook and bake. Oversized bedrooms and two bathrooms. Great for a weekend getaway (about 1hr drive from NYC). EV friendly - Tesla universal charger located at property to charger your Tesla or EV vehicle (integrated J1772 adapter) during your stay.

4.96 out of 5 average rating, 179 reviews

Top guest favorite

A warm wooden interior is featured, with wall art depicting horses and rural scenes. A rustic wooden table is positioned near the window, and a candle sits at its center. A potted plant adds a touch of greenery beside a cozy armchair.

Farm stay in Redding

Charming Historic Cottage in the Redwoods

Travel back in time to Marchant Farm and enjoy an authentic farm life experience in the historic, newly restored Sunflower Cottage. Whether you need a place to recharge or to reconnect with nature, you will find it here. Relax and unwind in the stunning floor to ceiling cedar living area. With 2 air conditioned bedrooms, each with full beds, and the children's magical loft space with two twin beds and play area.

4.98 out of 5 average rating, 103 reviews

Top guest favorite

Home in Redding

Retreat with Heated Pool, 1 Mile to NYC Train

The pool is open for the 2026 season. Escape to a stunning 4-BR home on 2 acres in Redding, CT (#1 Small Town). Just 90 mins from NYC, this luxurious retreat comfortably fits 8 guests. Enjoy hotel-style amenities, a heated saltwater pool, and a gourmet kitchen. Breathe in fresh country air in a peaceful, park-like setting. Perfect for families, offering a blend of modern comfort and outdoor living.

4.99 out of 5 average rating, 109 reviews