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Our top choices for South Shaftsbury holiday rentals

1. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!Hoosick Falls
9.8 out of 10, Exceptional, (118 reviews)
The price is €337
includes taxes & fees
15 Nov - 16 Nov

2. West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub
West Barn Suite at Hubbell Homestead - Mountain Views & Jetted TubBennington
The price is €250
includes taxes & fees
10 Nov - 11 Nov

3. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT RetreatBennington
8.6 out of 10, Excellent, (36 reviews)
The price is €261
includes taxes & fees
11 Nov - 12 Nov

4. 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, VermontWoodford
10.0 out of 10, Exceptional, (1 review)
The price is €467
includes taxes & fees
10 Nov - 11 Nov

5. East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted TubBennington
The price is €250
includes taxes & fees
10 Nov - 11 Nov

6. Peaceful Cottage Retreat
Peaceful Cottage Retreatcambridge
9.8 out of 10, Exceptional, (50 reviews)
The price is €165
includes taxes & fees
10 Nov - 11 Nov

7. Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
Seasons ski-in/ski-out condo with balcony and wood-burning fireplaceDover
8.6 out of 10, Excellent, (37 reviews)
The price is €317
includes taxes & fees
10 Nov - 11 Nov

8. Spacious apartment in beautiful, historic Arlington VT
Spacious apartment in beautiful, historic Arlington VTArlington
10.0 out of 10, Exceptional, (66 reviews)
The price is €238
includes taxes & fees
10 Nov - 11 Nov

9. Cozy Home in Pownal VT
Cozy Home in Pownal VTPownal
10.0 out of 10, Exceptional, (15 reviews)
The price is €179
includes taxes & fees
15 Nov - 16 Nov

10. Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible viewsshushan
9.6 out of 10, Exceptional, (27 reviews)
The price is €328
includes taxes & fees
10 Nov - 11 Nov

11. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain DenDover
9.4 out of 10, Exceptional, (23 reviews)
The price is €286
includes taxes & fees
18 Nov - 19 Nov

12. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and DowntownNorth Adams
8.0 out of 10, Very good, (2 reviews)

13. Little River Cottage
Little River CottageSalem
The price is €241
includes taxes & fees
10 Nov - 11 Nov

14. New Studio In Town, By the Water
New Studio In Town, By the WaterWilliamstown
10.0 out of 10, Exceptional, (21 reviews)
The price is €252
includes taxes & fees
15 Nov - 16 Nov

15. Cozy 3 bedroom condo 2.5 miles to Mount Snow
Cozy 3 bedroom condo 2.5 miles to Mount SnowWest Dover
9.2 out of 10, Wonderful, (52 reviews)
The price is €276
includes taxes & fees
1 Dec - 2 Dec

16. Fourth-floor Stratton Village studio with valley-view balcony
Fourth-floor Stratton Village studio with valley-view balconyStratton
The price is €206
includes taxes & fees
10 Nov - 11 Nov

17. Downtown | Waterfront | Walk to Shops
Downtown | Waterfront | Walk to ShopsWilliamstown
9.8 out of 10, Exceptional, (13 reviews)
The price is €268
includes taxes & fees
15 Nov - 16 Nov

18. Long Trail House at Stratton Mountain Resort
Long Trail House at Stratton Mountain ResortStratton
8.6 out of 10, Excellent, (85 reviews)
The price is €396
includes taxes & fees
10 Nov - 11 Nov

19. Long Trail House 368 condo in Stratton Village, walk to the lifts
Long Trail House 368 condo in Stratton Village, walk to the liftsStratton
The price is €233
includes taxes & fees
10 Nov - 11 Nov

20. The Eagles Wing at The CHM - Private Apartment
The Eagles Wing at The CHM - Private ApartmentDover
9.8 out of 10, Exceptional, (6 reviews)
The price is €116
includes taxes & fees
11 Nov - 12 Nov
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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