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, 148 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.

Top guest favorite

Cottage in Perry

4.98 out of 5 average rating, 138 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.

Top guest favorite

Apartment in Chaffee

4.95 out of 5 average rating, 102 reviews

The Smart Choice

Leave your worries behind & reconnect with friends and family. "The Smart Choice" sleeps up to 6 guests and is full of smart home devices. It is the perfect quiet getaway from the city. Spend your evenings gazing at the stars in the country night's sky or curled up in front of a warm cozy fireplace. Approximately 35 mins. from: Letchworth State Park, Holiday Valley & The Buffalo Bills Stadium. Also, we are right on the snowmobile trail. An ideal getaway for a relaxing stay in any season!

Top guest favorite

Home in Orchard Park

5 out of 5 average rating, 245 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

Guest suite in Lancaster

4.98 out of 5 average rating, 167 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 dog Toby & our cat Taffy who will welcome you (but will not be a bother) we invite you to enjoy our home.

Guest favorite

Bungalow in Bliss

4.91 out of 5 average rating, 246 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

Home in Perry

4.96 out of 5 average rating, 130 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

Home in East Aurora

4.99 out of 5 average rating, 107 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

Apartment in Albion

4.98 out of 5 average rating, 170 reviews

Lagom Living Not too little ~ Not too Much

Our Airbnb is an entire two-bedroom apartment in an 1800s home in Albion, NY. You’ll have plenty of room to settle in and stretch out here. We can sleep five people on two double beds and a couch. The comfortable living room is stocked with board games and our full kitchen has all the appliances and kitchenware you need to make your own meals. With onsite parking, a private entrance, and washer and dryer, you can really make yourself at home.

Top guest favorite

Apartment in South Wales

4.96 out of 5 average rating, 182 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.

Top guest favorite

Cabin in Bliss

4.93 out of 5 average rating, 139 reviews

Escape to the A-Frame Cabin

Our charming cabin, renovated with modern amenities, is nestled on 3 acres of picturesque woodland, near state land, perfect for families or friends seeking outdoor adventures. Enjoy a comfortable bedroom, a loft area for extra guests, and breathtaking views from the large deck. Immerse yourself in nature, and stay connected with high-speed WIFI. Book your stay today to experience peace and serenity in our little slice of paradise.

Top guest favorite

Apartment in Strykersville

4.99 out of 5 average rating, 238 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*