Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

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Top guest favorite
A welcoming front porch features a small round table with two chairs positioned under a covered area. Lush green bushes frame the space, surrounded by a wooden railing and steps leading to the entrance of the home.
Home in Warsaw
4.95 out of 5 average rating, 360 reviews

Front and Center

Warm and cozy home from the turn of the century. Well maintained with all original wood trim. All bedrooms and bath upstairs on second floor. Appliances, dishes and everything you need to make a meal. Open front and back porches and a big back lawn. Short walk to a movie theater, home-made ice cream, great restaurants and a brewery. 20 mins to Letchworth State Park, 15 mins to Silver Lake, 1 1/4 hours to Niagara Falls. Near Class A Trout streams. No extra cleaning fee (just don't leave a mess)

Top guest favorite
Home in Buffalo
4.96 out of 5 average rating, 122 reviews

Oasis | Poker, Patio, Media Rm, Fire Pit, Pool

Key Features: 🔹 2 kings, 2 queens, 1 full, 2 twins, 1 toddle bed, 1 folding mini crib, 1 queen air mattress 🔹 Swimming pool 🔹 Poker and foosball tables 🔹2 Living rooms AND game room 🔹 3 fireplaces & fire pit 🔹 Kids play space & amenities 🔹 Outdoor dining, BBQ, & lounge space Located in Amherst, NY, Oasis is perfect for extended, multi-generational families, wedding parties, a mature girls getaway, or large groups traveling together with sleeping for 12 comfortably (+baby & toddler).

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, 261 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.

Guest favorite
A large private deck features several Adirondack chairs facing a scenic view. A small table is positioned at the center, holding a decorative lantern. The sun sets on the horizon, casting a warm glow over the landscape of farms and fields.
Bungalow in Bliss
4.89 out of 5 average rating, 264 reviews

Bungalow in Bliss

Enjoy beautiful views from this quaint bungalow, perched on a hillside in the heart of farm country in Wyoming County, NY. Open concept space. Modern appliances. Retro lighting. Adirondack style furniture. Plenty of windows for natural lighting. Enjoy the panoramic view of the sunrise, sunset on the huge, private deck. Plenty of restaurants, convenience store, small towns in any direction, lake, river, parks and hiking trails nearby. Plus, enjoy Letchworth State Park just minutes away!

Top guest favorite
A spacious living area features large windows allowing natural light to fill the room. A comfortable sofa with decorative pillows is positioned alongside a modern coffee table. In the background, a well-equipped kitchen is visible, showcasing dark cabinetry and stylish fixtures.
Apartment in East Aurora
4.98 out of 5 average rating, 135 reviews

Large 2 bed 2 bathroom loft in East Aurora Village

Centrally located in the heart of East Aurora, this loft style apartment is one of one! That means the entire top floor of the building is yours and completely private. This unit features 2 bedrooms (king and queen beds) and 2 full bathrooms. You’ll enjoy the high end finishes and A+ views overlooking the village. This home is large so there is privacy. Feels like 2 apartments in one if you’re traveling with friends or children to have your own space, separate bathrooms etc!

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
4.97 out of 5 average rating, 119 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
4.99 out of 5 average rating, 262 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*

Top guest favorite
A charming cottage is set against a vibrant sunset sky, with soft hues illuminating the surrounding trees. The front entrance is framed by a welcoming porch, leading to a grassy area that gradually slopes away from the building.
Cottage in East Aurora
4.91 out of 5 average rating, 195 reviews

Charming 2 bedroom cottage on the EA golf course

Welcome to Maplelinks. Relax at this quiet and quaint 100 year old 2 bedroom/1 bathroom guest cottage located right on the East Aurora Country Club less than a mile outside of the village. 15 minutes from Bills games. 20 minutes from downtown Buffalo. 20 minutes from skiing. Private off street parking. Self check-in anytime after 3pm. (Sorry. No pets.)

Top guest favorite
A cozy corner features a brick fireplace, framed by decorative plants and two lace-covered windows. A small wooden table stands beside the fireplace, adorned with a candle and vintage items. Nearby, a set of folding chairs is positioned next to a framed floral artwork.
Apartment in Buffalo
4.92 out of 5 average rating, 276 reviews

Peaceful, spacious apartment. Non-smoking.

Traditional South Buffalo lower in the Irish Heritage District. NOT suitable for children aged 1-12. NOT pet-friendly. 10 minutes from Canalside, Key Bank Center, Sahlen Field, Harbor Center, Riverworks and downtown. 20 minutes from Highmark Stadium. 30 minutes from Niagara Falls. Stumbling distance from the Buffalo Irish Center.

Top guest favorite
Apartment in Chaffee
4.99 out of 5 average rating, 137 reviews

The Hidden Gem East

Renovated 3 bedroom situated on a large lot with parking parking for 3-4 vehicles. My place is a duplex and each side sleeps 6 people. I like to refer them as the West side and the East side. This apartment is the East side and it is new from Top to Bottom. I think your going to love it

Top guest favorite
The intimate porch is adorned with vibrant hanging flower baskets and softly lit torches. Lush greenery surrounds the area, enhancing the secluded atmosphere of the space. A glimpse of the tree-lined street is visible in the background.
Guest suite in Allentown
4.95 out of 5 average rating, 1,810 reviews

Buffalo's Allentown Area Apartment

The apartment itself is newly furnished and has its own private entrance. It is a one-bedroom apartment with a queen size bed. For an extra guest the living room is furnished with a roomy sofa bed. Intimate porch for morning coffee in the beautiful historic Allentown neighborhood.

Guest favorite
A serene outdoor fire pit area is surrounded by comfortable blue chairs and natural stone. A gravel path leads to the water's edge, with logs stacked nearby for easy access. Green ferns and blooming flowers add a touch of nature to this peaceful retreat.
Cottage in Castile
4.82 out of 5 average rating, 387 reviews

The Bluebird Cottage on Silver Lake

Minutes from the entrance to Letchworth State Park!Washer, dryer, quality linens and towels. Unobstructed view of the lake. Great fishing, swimming and kayaking via the State boat launch or Perry Public Beach. Very peaceful and quiet, with a great fire pit area.

Popular amenities for Bennington vacation rentals

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