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Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

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Top guest favorite
Farm stay in Cattaraugus
5 out of 5 average rating, 157 reviews

The Guest House at Burdick Blueberries Farm

Share the peaceful beauty of our working family blueberry and flower farm with organic and sustainable practices. Located in East Otto, New York. During the blueberry season experience the joyful bustle of the pick-your-own blueberries and flowers, Mid-July - August. Private guest house attached to farmhouse. Enjoy our patio and spacious lawns plus in-ground pool. Walk along the blueberry bushes, farm roads and woodland trails. Guest space has a simple & natural aesthetic, a relaxing haven.

Guest favorite
A charming, dark blue cottage is framed by lush greenery and vibrant purple flowers. The cobblestone pathway leads to a bright yellow front door, welcoming guests. Various flowering plants provide color and texture to the well-maintained garden, enhancing the inviting exterior.
Cottage in Niagara Falls
4.96 out of 5 average rating, 345 reviews

Charming Carriage House in Niagara's Wine Country

A converted carriage house and former blacksmith shop with a rich history dating back to the 1800’s - updated with brand new modern amenities. This is a one level plus loft bedroom, ideal for those who have challenges with stairs. Centrally located near the Falls, Niagara Parkway, Niagara-on-the-Lake, casinos, wineries and the largest outlet mall in Canada (car recommended). A great gathering spot in any season with a full kitchen, laundry and outdoor space ready to entertain family and friends.

Top guest favorite
A large two-story house is surrounded by a well-maintained lawn featuring green grass and a variety of trees. The front porch is covered and supported by wooden beams, inviting outdoor gatherings. A clear blue sky complements the home, enhancing the serene setting.
Cottage in Perry
4.97 out of 5 average rating, 148 reviews

16 Sandals

Come enjoy the friendly neighborhood in our cozy lake front home. Bring your fishing boats, kayaks, canoes and fishing poles! Spend the day on the lake or on our large lake view patio, then unwind at night at our fire pit or in the hot tub! Nearby, you can find a drive-in movie theater, mini golf and ice cream- fun for everyone! In the winter months, bring your snowmobiles to enjoy direct access to hundreds of miles of marked and groomed snowmobile trails including nearby Letchworth State Park.

Guest favorite
The exterior of a renovated farmhouse from the 1870s is shown, featuring light-colored siding and green trim. A welcoming porch extends across the front, showcasing a sign with the address. Tall trees are visible in the background, contributing to the rural setting.
Apartment in East Aurora
4.95 out of 5 average rating, 120 reviews

The Farmhouse we call Genevieve

This circa 1870’s Farmhouse has been newly renovated including furnishings furnishes and utilities . The first floor rental space features a private entrance porch overlooking the park like property . Located just one mile from the Village of East Aurora this property features nature trails to the banks of Cazenovia creek . Ideal for family’s with children and also Pet Friendly. The living space is an easy 3 steps up to the private porch . Sleeps up to 5,Nice place to entertain or just relax

Top guest favorite
Place to stay in East Aurora
4.98 out of 5 average rating, 141 reviews

Large 2 bed 2 bathroom loft in East Aurora Village

Located in the heart of East Aurora, this 2nd floor loft is perfect and 1 of 1! The entire second floor is yours and there are no other units or shared entrances. It is like 2 spaces in one. 2 bedrooms (king and queen beds), 2 full bathrooms, and 2 living spaces. High end finishes and A+ views overlooking the village. Feels like 2 places in one if you’re traveling with others, you'll have your own space! Perfect for traveling in for a Bills game and walking distance to all things East Aurora!

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, 267 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
Castle in Elmwood Village
4.89 out of 5 average rating, 302 reviews

King Fireplace Luxury Rooftop Loft Gym Bball EV+

Experience the unique luxury! Perfect for family, business, or romantics. With high end finishes, 16' ceilings, a stunning 6' fireplace, this space exudes comfort & elegance. Unwind in the 5' round tub, or enjoy a movie on the 85' smart tv, while appreciating the building's history. For the active guests, an indoor basketball court and gym. Office area for business travellers. Seasonal rooftop area for sunsets or enjoying the weather. Additional bedrooms can be added for larger groups.

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.

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, 157 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

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, 123 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 friendly Akita is seen standing on a wooden porch, with two front doors visible in the background. Seasonal wreaths adorn the doors, and a potted plant adds a touch of greenery beside a decorative metal stand. A chair and cushion are also present on the porch.
Apartment in Buffalo
5 out of 5 average rating, 103 reviews

Bear's Den

Quiet three bedroom apartment with new kitchen and all appliances. Off the main roads but still close to Bills Stadium and Downtown Buffalo/Canalside. 30 minutes from Niagara Falls. Lots of parks and nature trails nearby. Large backyard. We have included photos of Bear our Akita, so you will know to expect a large dog on site/in the backyard etc. He loves people and children and loves to say hello. We cannot allow other pets on site because of Bear.

Top 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
4.96 out of 5 average rating, 203 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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