Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

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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
4.95 out of 5 average rating, 155 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, 42 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.

Top guest favorite
The farmhouse exterior is showcased, featuring a white clapboard facade complemented by a stone chimney. Vibrant rose bushes add color near the entryway, while lush greenery enhances the natural surroundings. Large windows provide a welcoming appearance amidst a well-maintained lawn.
Home in Niagara-on-the-Lake
4.94 out of 5 average rating, 103 reviews

Waterfront Niagara-On-The-Lake Vineyard Farmhouse

Experience this dreamy farmhouse with stunning seasonal vineyard and waterfront views, nestled between the Niagara River and Inniskillin Winery. Enjoy stylish contemporary interiors, a cozy gas fireplace, and a clawfoot tub. Perfectly located by top vineyards and Niagara trail, minutes from historic Old Town, this 3-bed, 3-bath retreat is ideal for group getaways, bridal parties, and special occasions. *Weddings view Property Description IG/TT: @willowfarmhousenotl NOTL STR License No. 079-2022

Top guest favorite
A modern kitchen showcases white cabinetry and a marble countertop. A central island features a wooden countertop with orange stools positioned around it. Stainless steel appliances, including a refrigerator and oven, are visible alongside a mosaic tile backsplash. Natural light fills the space.
Home in Orchard Park
5 out of 5 average rating, 268 reviews

Luxury Village Farmhouse

Welcome to our charming, old (but newly renovated!) Orchard Park Village Farmhouse! Large, but cozy, living and dining spaces and a huge kitchen with all the amenities. We have 2 large bedrooms, each is a "master suite" with bathroom and walk-in closets. In one bedroom, the king bed can be converted to 2 twins, if required. Queen sleeper sofa in living room. We're a short 1/4 mile walk to all the village shops, restaurants and coffee shops. 2 off-street parking spaces, wifi, AC, and laundry.

Top guest favorite
Home in Attica
5 out of 5 average rating, 8 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 comfortable living area features a cozy fireplace set within a brick accent wall, providing a focal point. A large TV is positioned nearby, while a soft leather sofa and a vibrant orange chair offer ample seating. Natural light enters through the windows, enhancing the inviting ambiance.
Apartment in Clarence
4.99 out of 5 average rating, 159 reviews

Meticulous Main St. Ranch 2 Bd Lux Apt. Rear Unit

This well-appointed, recently renovated, 1200 sq. ft. ranch duplex apt. is located on Main St in the heart of charming & historic Clarence, NY. The community is a beautiful, safe, and family friendly suburb of Buffalo, NY. The entire apt. is on one level, with four parking spaces next to the entrance. The beautiful open concept floor plan provides an abundance of natural lighting, creating a comfortable airy feeling, that is perfect for small gatherings, business travelers, and entertaining.

Guest favorite
A cozy bedroom features a wooden sleigh bed with a plaid comforter. A decorative lamp sits on a nightstand beside the bed. A trunk labeled 'LOVE' is placed at the foot of the bed, and a window with a checkered valance allows natural light to filter in.
Guest suite in Lancaster
4.96 out of 5 average rating, 195 reviews

"The Suite Spot", Adorable apartment with deck

Kick back and relax in this calm, stylish space. This second floor apartment boasts a newly remodeled bathroom, a full kitchen, a comfortable bedroom perfect for two & a cozy sitting area with chairs that convert into twin beds. It also offers off street parking for one vehicle & a private entrance on the deck. It's a perfect place to relax & enjoy the summer & fall. Along with our cat Taffy who will welcome you (but will not be a bother) we invite you to enjoy our home.

Top guest favorite
Apartment in Chaffee
4.99 out of 5 average rating, 149 reviews

The Hidden Gem - West

This brand new renovated 3 bedroom 1 bath duplex is the perfect place to stay, whether your visiting family in Western NY or just visiting to enjoy all of the beauty of our great state. All brand new appliances, washer and dryer and central AC to keep you cool in the hot summer months. We are approximately 30 minutes from Holiday Valley for some great skiing, just off the snowmobile trail for some great snowmobiling and the ATV and SXS trails are popping up all around us.

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, 159 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
The exterior of the historic colonial home features a welcoming facade, with an American flag displayed prominently. Lush greenery surrounds the entryway, enhanced by flowering planters. A decorative black fence encloses a well-maintained lawn, creating a charming and inviting atmosphere.
Guest suite in Corfu
4.95 out of 5 average rating, 38 reviews

Iron Gate Property

Unwind in this Historic 1863 colonial style home. Fully restored three bedroom and two bath suite. Located in between Rochester and Buffalo, a quick 5 minute drive off of the thruway in the small quaint village of Corfu. 5 minute drive to Darien Lake Theme Park/ Live Nation Theater and Darien Lake State Park. *No kitchen/hotel like setting Other treasures within 45 minute drive or less include Letchworth State Park, Niagra Falls, wineries and Breweries

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, 124 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

Top guest favorite
A comfortable living area features a gray sofa adorned with decorative pillows. Nearby, a round leather ottoman complements a patterned rug. A tall floor lamp provides soft lighting, and a potted plant adds a touch of greenery to the space. Artwork is displayed on the walls.
Apartment in Strykersville
4.98 out of 5 average rating, 264 reviews

Suite and Simple - Private 3rd Floor Efficiency

Suite and Simple is a private, upstairs suite on a quiet country hillside. It is 15 minutes from the village of East Aurora, about 30 minutes from downtown Buffalo and minutes from local wedding venues. Whether you're just passing through, or in town for an event, this suite has the essentials for a restful stay. *There are 2 flights of stairs to get to the suite*

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