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Latest Vacation Rentals in Bennington VT (25)

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4 Br Private Vacation Home Vacation Rental In Bennington, Vermont

Are you looking for a private pool, hot tub that holds 8, sauna, AND a playground!? Look no further. Join us in our guest house at Karin's Place and enjoy our Gentleman's Farm of goats, chickens,...

Created Jun 16, 2024

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1 Br Guest House Vacation Rental In Bennington, Vermont

AMENITIES: FREE Daily Breakfast, Individual Climate Control, Cable/Satellite TV, Seating Area, Functional Work Desk, Hairdryer, Iron/Ironing Board, Minifridge, Microwave, Coffee Maker, Free WiFi,...

Created Jun 16, 2024

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3 Br Apartment Vacation Rental In Bennington, Vermont

Welcome to the Cozy Getaway, a newly renovated 3-bedroom condo on Branch Street in beautiful Bennington, Vermont. This charming and comfortable home is perfect for small families or business...

Created Jun 16, 2024

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5 Br Agritourism Vacation Rental In Bennington, Vermont

White Rock Farm is a 295-acre working farm in Bennington VT, a three hour drive from New York or Boston. it is part of the scenic and historic Valley of Vermont and surrounded by the Green and...

Created Jun 16, 2024

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3 Br Agritourism Vacation Rental In Shaftsbury, Vermont

Welcome to The Barn Retreat where comfort, adventure, and relaxation seamlessly intertwine. Book your stay today and create memories that will last a lifetime. The Barn Retreat a meticulously...

Created Jun 16, 2024

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3 Br Cottage Vacation Rental In Woodford, Vermont

This cottage is nestled in the mountains of Woodford VT, in a private location directly on the lake. You will experience sheer delight during your stay at the Honey Bear Lake Cottage!Choose from...

Created Jun 16, 2024

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2 Br Cabin Vacation Rental In Bennington, Vermont

Experience true beauty at this 100-acre Big Sky vacation rental. This secluded cabin is immersed in nature, making it easy to unwind. This abode brings comfort to a new level, featuring 2 bedrooms,...

Created Jun 16, 2024

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1 Br Guest House Vacation Rental In Bennington, Vermont

AMENITIES: FREE Daily Breakfast, Individual Climate Control, Cable/Satellite TV, Seating Area, Functional Work Desk, Hairdryer, Iron/Ironing Board, Minifridge, Microwave, Coffee Maker, Free WiFi,...

Created Jun 16, 2024

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4 Br Cabin Vacation Rental In Woodford, Vermont

-Make unforgettable memories at our newly renovated, unique, cozy Cabin and Barn in the Green Mountain Forest with endless adventures from the front door.-Snowmobile from the driveway to the VAST...

Created Jun 16, 2024

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3 Br Cabin Vacation Rental In Woodford, Vermont

3 Bedroom log-sided cabin with large deck facing Woodford Lake with beautiful lake view. High ceiling Great Room with lots of space, private onsite parking, in quiet lakeside community - complete...

Created Jun 16, 2024

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1 Br Private Vacation Home Vacation Rental In Bennington, Vermont

Immerse yourself in a relaxing retreat at this 1-bedroom, 1-bathroom vacation rental nestled in the heart of Bennington, Vermont! Begin your days marveling at breathtaking mountain views from the...

Created Jun 16, 2024

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5 Br Private Vacation Home Vacation Rental In Bennington, Vermont

Newly Renovated Cape with Function, Comfort, & StyleThis amazing 5 bedroom 4 bath Cape Cod has been completely renovated. It features a chef's kitchen with an 8 burner stove, new Game Room, 3 king...

Created Jun 16, 2024

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2 Br Cottage Vacation Rental In Bennington, Vermont

Walk out the door for an adventure on the Molly Stark Trail during the winter season and beach side on Woodford Lake during the summer. Woodford State Park is 3 miles from the cottage. Woodford...

Created Jun 16, 2024

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3 Br Cottage Vacation Rental In Woodford, Vermont

Escape with the whole family to this peaceful home in a lakeside community bordering Green Mountain National Forest. There is EVERYTHING to do here for nature and outdoor recreational enthusiasts...

Created Jun 16, 2024

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1 Br Bed & Breakfast Vacation Rental In Bennington, Vermont

The estate, formerly the private residence of Louis A. Graves, was the creation of architect William C. Bull who designed many of the stately Victorian structures in the Shires of Vermont. Ten-foot...

Created Jun 16, 2024

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3 Br Private Vacation Home Vacation Rental In Bennington, Vermont

This home was originally built in the mid-1800's. It has been completely remodeled to preserve the historic beauty of the home. Modern conveniences were added. The house is located two blocks off...

Created Jun 16, 2024

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3 Br Private Vacation Home Vacation Rental In Bennington, Vermont

Very comfortable accommodations with just about everything brand new down to quality mattresses and bedding. New kitchen appliances and compliments along with bottled spring water in the fridge....

Created Jun 16, 2024

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3 Br Private Vacation Home Vacation Rental In Bennington, Vermont

Just 2 miles from the Downtown Bennington Historic District, this 3-bed, 2-bath vacation rental in Vermonts first town seamlessly combines New England charm with outdoor adventure. Spend summer...

Created Jun 16, 2024

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3 Br Cottage Vacation Rental In Bennington, Vermont

Cozy Woodford Lakefront Cottage is perfect vacation spot for families and outdoor enthusiasts or those seeking a relaxing get away. The cottage sits high overlooking Woodford Lake with a...

Created Jun 16, 2024

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1 Br Guest House Vacation Rental In Bennington, Vermont

AMENITIES: FREE Daily Breakfast, Individual Climate Control, Cable/Satellite TV, Seating Area, Functional Work Desk, Hairdryer, Iron/Ironing Board, Minifridge, Microwave, Coffee Maker, Free WiFi,...

Created Jun 16, 2024

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Apartment Vacation Rental In Bennington, Vermont

Whether you're coming to Bennington for the fall colors, winter sports, spring graduations, summer street festivals and parades, or college campus visits, this studio apartment will provide a...

Created Jun 16, 2024

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2 Br Apartment Vacation Rental In Bennington, Vermont

Breathtaking views up & down Main Street. In the heart of downtown Bennington, steps from the four corners of US Rte 7 and VT Rte 9, walk to all downtown shops, restaurants, banks, post office and...

Created Jun 16, 2024

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6 Br Private Vacation Home Vacation Rental In Bennington, Vermont

Exceptional home with 6 bedrooms, 5 full bathrooms, 2 half bathrooms.Bar room perfect for entertaining guests.Game room, complete with an Xbox One and convertible game table.10 minute walk from...

Created Jun 16, 2024

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3 Br Private Vacation Home Vacation Rental In Woodford, Vermont

Welcome to our high mountain lakeside getaway. Known fondly as Meme's lake house, let us show you why Vermont is the destination for every season.Meme's lake house boast 100 feet of private,...

Created Jun 16, 2024

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2 Br Private Vacation Home Vacation Rental In Woodford, Vermont

About this spaceDreamy Vermont log home tucked away in the woods but close to the conveniences of town. Charming, and modern and efficient. We have super fast wifi so its perfect for working...

Created Jun 16, 2024

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