Places to stay near Hopkins Vineyard

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Top-rated vacation rentals near Hopkins Vineyard

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

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Guest favorite
A historic farmhouse is set among vibrant greenery and blooming orange flowers. The expansive front porch features classic white railings and is lined with hanging planters. The structure is nestled between two large trees, providing a serene backdrop against the clear blue sky.
Guest suite in Dover Plains
4.91 out of 5 average rating, 350 reviews

Hoppy Hill Farm House

Enjoy the simple country life in this historic farmhouse. Watch the sun rise over the breathtaking mountain views from the front porch while sipping a cup of coffee/tea. For the more adventurous, there are lots of Appalachian Trail hiking opportunities, and nature preserves to enjoy. Plenty of quaint towns near-by: Kent, Millbrook, Amenia, Wassaic for great food, coffee shops, antiques, parks, breweries and vineries. Inside, you will feel right at home in this comfortable one bedroom apartment.

Top guest favorite
A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.
Chalet in Otis
4.95 out of 5 average rating, 461 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Top guest favorite
The exterior of the modern chalet is surrounded by lush greenery, showcasing a spacious sun room with large windows. A hammock is visible between trees, inviting relaxation. The property features a gently sloping yard leading down to the tranquil lakefront.
Chalet in Carmel Hamlet
4.97 out of 5 average rating, 124 reviews

Secluded Lakefront Chalet•Firepit•Yard Dogfriendly

Just over an hour from NYC, this secluded, dog-friendly lakefront chalet offers 200’ of private shoreline, fenced yard and sunroom with serene lake views. Thoughtfully styled with collected pieces from my travels, it blends quiet luxury with modern comfort. Cozy up by the fireplace, enjoy vinyl or a movie, watch snowfall, spot wildlife, explore nearby trails, unwind by the fire pit and rest in the king-size bed. Romantic, peaceful, beautifully secluded – your perfect winter lake escape awaits.

Top guest favorite
A bright living area is designed with a gray sectional sofa and a coffee table. A vase of fresh flowers is placed at the center. Decorative oars and a scenic image adorn the walls, while natural light streams in through the front door.
Guesthouse in Rhinebeck
4.99 out of 5 average rating, 135 reviews

Country Suite Near Omega Institute & Rhinebeck

We designed our guesthouse with the comfort seeking guest in mind. Enjoy our comfy plush beds, soft bed linens, luxurious towels, and complimentary bath amenities for your ultimate getaway. Complimentary snack and beverage selections are also provided in our efficient kitchenette (no stove) which can accommodate light meals. Our 2nd floor guesthouse offers ductless HVAC to provide the ultimate comfort AC or heating as needed. Many guests comment on our relentless pursuit of cleanliness.

Guest favorite
A rustic cottage is nestled among tall trees, overlooking a flowing brook. A wooden bench sits on a grassy area, with large boulders nearby. The house features a deck and is surrounded by greenery, with a gravel driveway leading up to the front.
Cottage in New Milford
4.95 out of 5 average rating, 234 reviews

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Top guest favorite
A bright and airy bedroom features large windows with stunning river views. The spacious bed is dressed in white linens with a soft blue throw. Vintage lamps sit on each side of the bed, while intricate green pendant lights hang from a wooden ceiling.
Home in Catskill
4.95 out of 5 average rating, 232 reviews

HEAVEN ON EARTH - Hudson Riverfront Home

Voted #3 Most Romantic AirBnB Near NYC (Time Out NY). Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access yr round. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Kayaks/SUP/Fishing Poles provided. Enjoy brunch, dinner or high tea on the Gazebo suspended over the Hudson with a private chef. Explore Hudson, Woodstock....also only 30 mins to Hunter/Skiing/Snowboarding!

Superhost
A gentle waterfall cascades over rocky terrain, surrounded by autumn foliage in varying shades. The water flows into a clear pool, with smooth stones lining the edges. Tall trees in the background create a lush, green canopy, while fallen leaves blanket the ground.
Cabin in Rhinebeck
4.88 out of 5 average rating, 426 reviews

Sunset Bungalow-Mt views on 130acre forest & falls

Newly renovated private cabin on the ridge top of an 130 acre magical property with stunning western views and overlooking a historic farm & crystal clear lake. Explore the hiking trails, dip in the wading pools of the upper cascades, bike to town or simply enjoy the peaceful sounds of the 90ft waterfall on the property. Relax in a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplace, and comfortable bedroom- learn more at cascadafarm.com

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
4.96 out of 5 average rating, 427 reviews

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 inflatable two person kayaks are available for use from May 1 to November 1..

Guest favorite
Tiny home in New Marlborough
4.95 out of 5 average rating, 147 reviews

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Top guest favorite
An interior corridor is visible, featuring rustic wooden beams and a warm wood floor. To one side, a glass-paneled room can be seen, likely housing a cozy nook. Light enters from multiple sources, creating an inviting and bright atmosphere.
Cottage in Red Hook
4.98 out of 5 average rating, 713 reviews

bright serene + spacious barn @barn and bike

a bright serene space built by locals on the property we live on. we are in what we think is the most beautiful region of the Hudson River Valley - surrounded by pastoral beauty and dramatic landscapes. quaint yet cultured towns in all directions. please read the entire description & rules before booking • beyond 2 guests, the rate adds 50$/night/per person • please add dogs (2 max. 50$/per dog) when booking (no cats) • we look forward to having you here!

Top guest favorite
The interior features large windows allowing natural light to illuminate the space. A spiral staircase leads to the loft. A cozy seating area includes a white sofa and a decorative fireplace. Lake views are visible through the glass doors, enhancing the serene atmosphere.
Guesthouse in Brewster
4.99 out of 5 average rating, 325 reviews

The Cottage by the Lake: Hudson Valley Indulgence

The Cottage by the Lake is a cozy, secret get-away on the scenic banks of the Croton Watershed. About an hour from NYC, it’s on the property of an 1850 farmhouse & has a fully equipped kitchen & bath, cathedral ceiling, working fireplace & cozy sleeping loft. The patio has a fire pit and gas bbq. It’s the ideal place for those seeking to work from home.

Top guest favorite
A charming blue house is framed by a well-maintained lawn, featuring white trim and multiple windows. The entrance boasts a red door, and a small porch is adorned with chairs. Surrounding trees provide shade, contributing to a peaceful outdoor environment.
Guest suite in Kent
4.99 out of 5 average rating, 115 reviews

Bright 1-bedroom in walking distance to town

Super bright and comfortable 1-bedroom apartment includes parking, queen-sized bed, Nespresso & Coffee machines, two televisions, Wi-Fi, Netflix, HBO and Hulu. Walk to restaurants, or hike to one of the nearby trails that surrounds the town. Walking distance to the Kent School.

Popular amenities for vacation rentals near Hopkins Vineyard