Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

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

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Top guest favorite
A cabin is nestled among tall pine trees, showcasing a rustic wooden exterior and a welcoming porch. The surrounding landscape reveals vibrant autumn foliage in hues of orange and red, creating a serene and secluded atmosphere.
Cabin in Ellicottville
4.96 out of 5 average rating, 170 reviews

Stylish & Secluded Hideaway, 5 mins to EVL

This private space is quietly tucked away in a stand of pines in the woods alongside Bryant Hill Creek. A wall of windows brings nature and natural light pouring into the space, and a fully-equipped kitchen and European bathroom provide modern comfort. Less than 4 miles outside of E-ville, it comfortably sleeps 2 adults and offers a chic and romantic setting for a couple to hide away with easy access to downtown. 4x4 a must in the snow, or simply park at the foot of the driveway. Tv & wifi.

Top guest favorite
A welcoming entryway features light gray walls and a natural wood floor. A console table with decorative accents stands against the wall, complemented by a mirror. Natural light filters through the front door, which is adorned with a simple wreath.
Home in Akron
5 out of 5 average rating, 44 reviews

Home Sweet Akron

Relax and unwind in this brand new 3 bedroom home furnished in a beautiful modern farmhouse theme. Located within walking distance to the Akron/Clarence bike path and a 5 minute drive to Timerlodge, The Sterline and Akron Acres wedding venues. Home has an attached deck overlooking a pond to enjoy your morning coffee or a glass of wine @ sunset. The village of Akron is host to several resaurants and quaint shops. A park is situated right in the cente of town featuring a splash pad and gazebo.

Guest favorite
Home in Attica
5 out of 5 average rating, 13 reviews

Cute country cottage…

Enjoy the country at this cute cottage with lots of amenities. Whether a couples getaway, family vaca, girls weekend, or snowmobile trip, this property has what you need. Property sits on 4 acres, has an open floor plan & large lawn. Grill, drink wine, have camp fires, snowmobile, and/or visit some of WNYs great destinations. Close to Batavia, Darien Lake, Byrncliff, snowmobile trails, golf courses, restaurants, several breweries, and grocery store. The Bills & Letchworth are within 45 min.

Top guest favorite
A welcoming living area features a comfortable sectional sofa and a gray armchair. A coffee table sits on a patterned area rug, while soft light is provided by table lamps. The room is brightened by natural light from the windows and is designed for relaxation.
Home in Orchard Park
4.98 out of 5 average rating, 190 reviews

Cottage at Orchard Park Village

Cozy cottage nestled in the heart of the Village of Orchard Park, NY. Home has been renovated top to bottom but maintains it's original charm! Located in a very safe neighborhood on a quiet street. Walking distance to Village amenities (restaurants/bars/coffee shops) and minutes from Highmark Stadium (home of the Bills)! 15 minutes to downtown Buffalo, 20 minutes to Buffalo Niagara International Airport, and 40 minutes to Niagara Falls. **10% DISCOUNT FOR VETERANS AND ACTIVE DUTY WITH ID**

Guest favorite
A charming cabin nestled among tall trees showcases a grassy lawn in the foreground. The structure features a covered porch and large windows, blending harmoniously with nature. Soft sunlight filters through the branches, casting gentle shadows on the ground.
Cabin in Warsaw
4.94 out of 5 average rating, 32 reviews

Cozy Cabin Getaway on a Scenic Horse Farm

Our cozy cabin is a 1 bedroom, 1 bathroom that is perfect for a romantic getaway. Tucked back in the woods, it is the perfect place to unwind for the night. Our cabin is equipped with a full size fridge/freezer, kitchen, TV, AC, heat, and large living room. Our deck has a outdoor kitchen with a fridge, grill and a fireplace. The view that is offered at our cabin is like no other. This cabin is on the same property as a working horse farm. We also offer guided horseback rides to the public.

Guest favorite
A fenced-in area showcases a private heated pool surrounded by lush greenery and blooming flowers. Lounge chairs are positioned nearby on the patio, providing a space for relaxation. The pool features clear water and is well-maintained, inviting guests for a refreshing swim.
Home in Alden
4.91 out of 5 average rating, 118 reviews

Carols Country Inn ☆☆☆☆☆

Do you enjoy luxury? You and your family have our entire home to enjoy sleeps 5 Features : piano, fireplace, fenced in pool :vaulted gazebo Our home includes 3 bedrooms (queen beds) , 2 baths, master suite has bath Deep soaker tub & shower, washer/dryer a beautiful gazebo at the poolside , charcoal grill available, inground private heated pool. pool open may 28 2024 Our home is short drive to falls approx 40 mins Uber to Buffalo Niagara airport in 18 m Darien Lake (15 min

Guest favorite
Guesthouse in Strykersville
4.79 out of 5 average rating, 14 reviews

Jenn's Piece of Paradise Resort

Discover an enchanting destination specifically crafted for lovers seeking intimacy and relaxation. Unwind in our fully remodeled, romantically furnished, farmhouse themed home. Experience privacy with an inviting jacuzzi in your living room or enjoy breathtaking views from the outdoor hot tub. Our goal is to provide a serene atmosphere perfect for enjoying each other's company. Private access to the entire Bed and Breakfast, including three separate rooms upstairs for your enjoyment.

Guest favorite
A bridal gown is elegantly displayed on a hanger in a well-lit room. A large vintage mirror reflects the space, which features a cozy seating area with a leather sofa and a decorative circular rug. Natural light filters through sheer curtains, enhancing the inviting ambiance.
Home in Elma Center
5 out of 5 average rating, 32 reviews

Full House Rental with a focus on Wedding Day Prep

Welcome to Blanc Silk! We are a house rental with a focus on Wedding Day Prep. 👰‍♀️ We also welcome Buffalo Bills and Football Fans! 🏈 Approximately 15 mins from the stadium! Our spacious and unique home is perfect for wedding day bridal preparations and Bill games! Our house Includes a bridal suite along with a separate beauty styling lounge. When staying with us, your rental includes, outdoor property, gardens and ground for fabulous photo opportunities.

Top guest favorite
A welcoming exterior view of a remodeled country home is showcased, featuring a screened porch with dark trim and a white door. Lush greenery surrounds the property, complemented by freshly landscaped flower beds and a gravel pathway leading to the entrance.
Home in Perry
4.97 out of 5 average rating, 171 reviews

Peaceful Country Home

A peaceful clean home for you to enjoy!! We have a very nice size yard for camp fires and just relax in without any neighbors.Welcome to a peaceful country home in the middle of several very large ponds. Relax on the covered screened porch or the back deck for peaceful meals or just some bird watching. Not super far off the road but you feel like it. Road is pretty quiet and lots of wild life. Ponds and woods not our property so please stay in yard/ grass only

Guest favorite
An open-concept kitchen and dining area is illuminated by recessed lighting. A dining table with four chairs stands beside a large window, which offers views of the deck outside. A modern kitchen with stainless steel appliances and a central island can be seen, enhancing the space's functionality.
Guesthouse in East Aurora
4.95 out of 5 average rating, 44 reviews

The Overlook

Welcome to The Overlook! Stay in a relaxing guesthouse that sleeps 4, with beautiful, serene views. Located just 9 minutes from historic village of East Aurora, 23 minutes from Orchard Park (home to the Buffalo Bills stadium), and 27 minutes from Downtown Buffalo. In East Aurora, enjoy boutique shopping, as well as many local favorite spots to eat. Spend a day in nature hiking at Hunter's Creek County Park or enjoy the countryside at Knox Farm State Park.

Top guest favorite
The exterior of the timber-frame home is shown, featuring large two-story windows and wood accents. A covered veranda extends from the structure, offering seating. Surrounding greenery and manicured grass enhance the natural setting, inviting a peaceful retreat in the countryside.
Home in East Aurora
4.98 out of 5 average rating, 125 reviews

Timber-frame home on 12 wooded acres

Featured in Buffalo Spree and Artvoice, this timber-frame home features stunning hickory and black walnut interiors illuminated by two-story windows that face the morning sun. Radiant floor heating and earthen-plaster climate design. Wake up in queen and king beds, lounge under covered verandas, and shop right next door at Thorpe’s organic farm store. • 7 minutes from the Village of East Aurora • 24 minutes from Bills stadium • 1 hour from Niagara Falls

Guest favorite
A living room features a comfortable sofa with a decorative yellow pillow and a futon couch. A wooden coffee table sits in front, accompanied by ambient floor and table lamps. Light wooden flooring and an inviting wall sign create a cozy atmosphere.
Apartment in South Wales
4.95 out of 5 average rating, 211 reviews

Cozy Apt Just Outside of East Aurora

A nice place to relax or get some work done! Features a great back porch that overlooks the property. Close to Moog, Fisher Price and the Gow School, this apartment has a large bedroom with a king-size bed. Comfortable living room has a full size futon for an extra bed when needed. We are less than 20 minutes from Kissing Bridge and Buffalo Ski Center. We're a quick 30 minute drive to the city of Buffalo and 40 minutes from Niagara Falls.

Popular amenities for Bennington vacation rentals

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