Bennington Area Rentals
From $238 per night (USD)VRBO
Artistic Nature Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Kalarama Cottage is a newly renovated space in the middle of nature! Make yourself right at home at this quiet, private ...
From $238 per night (USD)VRBO
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Stratton Village Ski-in/Ski-out
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
True ski-in / ski-out condo, located in Village Watch #3 at the bottom of Tamarack and Villager lifts. Quiet location, y ...
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From $486 per night (USD)VRBO
Escape to This Mountain Retreat Near Hiking Trails, Pools, and Golf Courses
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Get away from it all in this spacious and serene mountain retreat in Stratton, at the heart of Southern Vermont. Perfect ...
From $486 per night (USD)VRBO
From $518 per night (USD)Expedia
Newly Renovated 2BR - walk to lift; walk to Stratton Village; easy parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Newly renovated 2 bedroom condo at Ober Tal. * Easy walk to Tamarack lift. * (point) .3 mile walk to Stratton villag ...
From $518 per night (USD)Expedia
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Stratton Comfort & Convenience - Walk or Quick Shuttle to Village
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Styles Brook Townhome offers a great layout and convenient mountain location. 15-minute walk or quick shuttle ride to t ...
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From $280 per night (USD)Expedia
Reillys Rest-private home in Green Mtns, kid-pet friendly-Ski,Bike,Walk,Relax!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Reilly's Rest on Holden Hill Rd. is a private home on 6 acres located in a prime location to ski, bike, hike, walk and r ...
From $280 per night (USD)Expedia
From $570 per night (USD)VRBO
Cozy ski chalet - w/ Assoc amenities. 10 mins from Mount Snow
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled in the beautiful Green Mountains of southern Vermont, Swoosh Chalet is minutes from skiing (Mt. Snow), golfing, ...
From $570 per night (USD)VRBO
From $333 per night (USD)Expedia
Outdoor Enthusiasts Paradise in Beautiful Vermont!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Immaculate 3 bedroom 2 bath home located in the Chimney Hill 4 Season Resort community. Fishing, Hiking, Boating, Go ...
From $333 per night (USD)Expedia
From $620 per night (USD)VRBO
Treetop townhouse with Hot Tub and plenty of space for the whole family!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy a relaxing mountain getaway in this stunning treetop condo, located in Stratton, VT. With 4 bedrooms, 4 bathrooms, ...
From $620 per night (USD)VRBO
From $874 per night (USD)VRBO
Four Season Vermont Getaway with Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Quintessential Ski House located in Chimney Hill. Just 10-15 mins from Mount Snow & minutes from downtown Wilmington. Th ...
From $874 per night (USD)VRBO
From $402 per night (USD)VRBO
A cozy home nestled in the Green Mountains of Vermont!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Our cozy home is great in all seasons! Comfortably furnished, it is a great place to read in front of the fire, set out ...
From $402 per night (USD)VRBO
From $641 per night (USD)Expedia
Just steps away from Stratton Village
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to our cozy and convenient trailside condo, nestled between the Tamarack Triple Chair Lift and the Village Lift. ...
From $641 per night (USD)Expedia
From $279 per night (USD)VRBO
Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Log Ski Lodge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $279 per night (USD)VRBO
From $458 per night (USD)Expedia
Two bedroom Condo With Mountain View And Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
"Cozy 2-bed, 2-bath ski cabin with mountain views, fireplace, and village shuttle. Book your mountain getaway now! Mast ...
From $458 per night (USD)Expedia
From $377 per night (USD)VRBO
Fall Country Chalet-PET Friendly,AirHockey,GameRM w/CommunityPool and amenities
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Hideaway at Bear Lair Lane! This spacious 3-bedroom near Mount Snow offers a full kitchen, deck with gril ...
From $377 per night (USD)VRBO
From $394 per night (USD)VRBO
Sunny Stratton Townhome ~ 1 Mi to Skiing!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Experience the idyllic beauty of Stratton, VT, and stay in this lovely 3-bedroom, 2.5-bathroom vacation rental! Nestled ...
From $394 per night (USD)VRBO
From $393 per night (USD)VRBO
Ski-In Ski-Out OberTal F Building! Skiers and Lift Right Outside your Window!\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful 2 Bedroom, Ski-in / Ski-out Condo! Look out your living room window to the Tamarack Chair Lift and slopes. J ...
From $393 per night (USD)VRBO
From $736 per night (USD)VRBO
Cozy ski retreat 7 minutes from Stratton's Sunbowl!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Desired location for skiers (down hill mountain bikers, golfers and outdoor enthusiasts alike). Enjoy your stay with fam ...
From $736 per night (USD)VRBO
From $706 per night (USD)VRBO
Family sized condo steps from Stratton Mountain located in heart of the village.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
3Bd/3Ba condo conveniently located in the Landmark building in the village of Stratton Mountain, VT. This unit is steps ...
From $706 per night (USD)VRBO
From $463 per night (USD)Expedia
Stylish Chimney Hill Home - Close to Mt. Snow!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Perfect home to enjoy a quiet stay in Vermont. Located, in the desirable Chimney Hill neighborhood only a short ...
From $463 per night (USD)Expedia
From $1497 per night (USD)VRBO
Ski in Out Awesome/ Penthouse- Top two floors-Walk to All
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Fantastic location, we are right on the Mountain and a 50 yard walk to the Villager Lift! This Condo is our home away f ...
From $1497 per night (USD)VRBO
From $3390 per night (USD)VRBO
Great location!Walk to trail 3 min. Christmas 10% discount cfm by Dec,5 day min.
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
THE FAMILY SKI HOUSE Your family can walk to the slopes at their leisure and not depend on Mom and Dad to drive them t ...
From $3390 per night (USD)VRBO
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Secluded home with deck, hot tub, fireplace, woodstove, & foosball table
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Green Mountain Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
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From $541 per night (USD)VRBO
A Village location, Swimming Pool, Hot Tub & Sauna
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Walk to the Lift, Walk to the Village, Live the dream ! We keep our condo up to date, fresh paint, super clean, persona ...
From $541 per night (USD)VRBO
From $1096 per night (USD)VRBO
WONDERFUL LOCATION FOR UP TO 10 PEOPLE OR PERFECT FOR ONE FAMILY
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
SLOPESIDE Town Home, end unit, 3 floors. Great for 2 families or one family seeking a peaceful retreat after a long day ...
From $1096 per night (USD)VRBO
From $235 per night (USD)VRBO
Cozy Cabin on Chimney Hill - Close to Mt Snow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming 3 bedroom cabin nestled in the woods at the top of Chimney Hill on Haystack Mountain, a 15 minute drive from Mt ...
From $235 per night (USD)VRBO
From $260 per night (USD)VRBO
Summer getaway-walk to Stratton Village, tennis, fitness, and pool-Mtn. Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Important to know before booking: Non-smoking/vaping ID may be required for proof of age (minimum renter age is 28) Loca ...
From $260 per night (USD)VRBO
From $1234 per night (USD)VRBO
Luxury Ski In/Out House w/ Private Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Truly amazing ski in/out townhome located just feet from the trail, and a 365 day community heated outdoor pool. No walk ...
From $1234 per night (USD)VRBO
From $300 per night (USD)VRBO
Secluded forest hideaway with hot tub
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Vermont Summer Cabin sits on the edge of Green Mountain National Forest, set away from the road the house is almost ...
From $300 per night (USD)VRBO