
Bennington Holiday Rentals
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Our top choices for Bennington holiday rentals

1. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
2. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
3. West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub
West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub
4. Cozy Home in Pownal VT
Cozy Home in Pownal VT
5. Long Trail House at Stratton Mountain Resort
Long Trail House at Stratton Mountain Resort
6. Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown
7. Long Trail House 368 condo in Stratton Village, walk to the lifts
Long Trail House 368 condo in Stratton Village, walk to the lifts
8. Spacious apartment in beautiful, historic Arlington VT
Spacious apartment in beautiful, historic Arlington VT
9. East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
10. Historic Home with Colonial Charm in Manchester
Historic Home with Colonial Charm in Manchester
11. Founders Lodge condo at Stratton Mountain with gas fireplace
Founders Lodge condo at Stratton Mountain with gas fireplace
12. Fourth-floor Stratton Village studio with valley-view balcony
Fourth-floor Stratton Village studio with valley-view balcony
13. Stratton ski-in/ski-out condo steps from the lift with valley-view balcony
Stratton ski-in/ski-out condo steps from the lift with valley-view balcony
14. Cozy Bromley Retreat — Ski-In, Ski-Out
Cozy Bromley Retreat — Ski-In, Ski-Out
15. The Birchwood Cabin - Stunning Mountain Views
The Birchwood Cabin - Stunning Mountain Views
16. Modern Mountain Retreat w/ Chef’s Kitchen
Modern Mountain Retreat w/ Chef’s Kitchen
17. Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
18. Cozy 3 Bedroom Condo in the Heart of Manchester VT
Cozy 3 Bedroom Condo in the Heart of Manchester VT
19. Long Trail House South Wing 2B2B Condo
Long Trail House South Wing 2B2B Condo
20. ADA King Room w/ Roll-In Shower & Views
ADA King Room w/ Roll-In Shower & ViewsFind holiday rentals that suit your style
Top Bennington Hotel Reviews

Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown
Find out more about Bennington
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Bennington holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Bennington. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Bennington. Seeing all the best attractions is bound to make you fall in love with Bennington. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Bennington short-term rentals, that won’t be hard to do.




































































