Holiday rentals near South Main Street
We found 739 holiday rentals — enter your dates for availability
Find the perfect private holiday rental within easy reach of South Main Street. Holiday rentals provide the amenities that you need and want for your stay with friends, family or just your pet, such as Wi-Fi and a hot tub. What you'll find is a property to rent to meet everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - South Main Street
Showing deals for:17 Oct - 24 Oct
Image gallery for Cozy 2-bedroom cabin near Mount Snow 3 min drive
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Cozy 2-bedroom cabin near Mount Snow 3 min drive
West Dover, VT
7% off
Price is NZ$3,025
NZ$3,025
NZ$432 per night
includes taxes & fees
Image gallery for Beautifully decorated large private log home 10 minutes from the mountain.
1010 out of 10 rating
Exceptional
(6 reviews)
Beautifully decorated large private log home 10 minutes from the mountain.
West Dover, VT
8% off
Price is NZ$9,364
NZ$9,364
NZ$1,338 per night
includes taxes & fees
Image gallery for The dreamiest place in Southern Vermont!
1010 out of 10 rating
Exceptional
(5 reviews)
The dreamiest place in Southern Vermont!
Wilmington, VT
11% off
Price is NZ$4,928
NZ$4,928
NZ$704 per night
includes taxes & fees
Image gallery for Contemporary 4-BR Alpine Chalet 10-min to Mt. Snow
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Contemporary 4-BR Alpine Chalet 10-min to Mt. Snow
West Dover, VT
7% off
Price is NZ$5,021
NZ$5,021
NZ$717 per night
includes taxes & fees
Image gallery for Dog Friendly Chalet in the Woods w/ Pool, Mt. Snow, VT
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Dog Friendly Chalet in the Woods w/ Pool, Mt. Snow, VT
Wilmington, VT
8% off
Price is NZ$5,002
NZ$5,002
NZ$715 per night
includes taxes & fees
Image gallery for Modern Luxury Villa Near Mount Snow. Your Vermont Retreat Awaits!
8.48.4 out of 10 rating
Very good
(5 reviews)
Modern Luxury Villa Near Mount Snow. Your Vermont Retreat Awaits!
West Dover, VT
8% off
Price is NZ$6,180
NZ$6,180
NZ$883 per night
includes taxes & fees
Image gallery for 8 minutes to Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
1010 out of 10 rating
Exceptional
(18 reviews)
8 minutes to Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
West Dover, VT
8% off
Price is NZ$6,369
NZ$6,369
NZ$910 per night
includes taxes & fees
Image gallery for Welcome to Dancing Bear Lodge...The Rustic Charm of Southern Vermont
9.49.4 out of 10 rating
Exceptional
(11 reviews)
Welcome to Dancing Bear Lodge...The Rustic Charm of Southern Vermont
Wilmington, VT
7% off
Price is NZ$5,551
NZ$5,551
NZ$793 per night
includes taxes & fees
Image gallery for Stunning views of Lake Whitingham+ Minutes from downtown Wilmington!
1010 out of 10 rating
Exceptional
(6 reviews)
Stunning views of Lake Whitingham+ Minutes from downtown Wilmington!
Wilmington, VT
7% off
Price is NZ$3,815
NZ$3,815
NZ$545 per night
includes taxes & fees
Image gallery for Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow
1010 out of 10 rating
Exceptional
(132 reviews)
Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow
Wilmington, VT
5% off
Price is NZ$6,492
NZ$6,492
NZ$927 per night
includes taxes & fees
Image gallery for Nestled in the Woods of Chimney Hill--Very Close to Wilmington VT/Mt Snow
1010 out of 10 rating
Exceptional
(18 reviews)
Nestled in the Woods of Chimney Hill--Very Close to Wilmington VT/Mt Snow
Wilmington, VT
8% off
Price is NZ$5,089
NZ$5,089
NZ$727 per night
includes taxes & fees
Image gallery for Luxurious log home with stunning views
1010 out of 10 rating
Exceptional
(35 reviews)
Luxurious log home with stunning views
Wilmington, VT
16% off
Price is NZ$12,275
NZ$12,275
NZ$1,754 per night
includes taxes & fees
Image gallery for Enjoy cool evenings by the outdoor fire with an unlimited view of the stars.
9.89.8 out of 10 rating
Exceptional
(111 reviews)
Enjoy cool evenings by the outdoor fire with an unlimited view of the stars.
Wilmington, VT
8% off
Price is NZ$10,464
NZ$10,464
NZ$1,495 per night
includes taxes & fees
Image gallery for 6 Bedrooms/3 Baths Farmhouse-Wilmington-Mount Snow
9.69.6 out of 10 rating
Exceptional
(9 reviews)
6 Bedrooms/3 Baths Farmhouse-Wilmington-Mount Snow
Wilmington, VT
20% off
Price is NZ$6,846
NZ$6,846
NZ$978 per night
includes taxes & fees
Image gallery for Beautiful log home close to Mt. Snow with hot tub and sauna.
1010 out of 10 rating
Exceptional
(32 reviews)
Beautiful log home close to Mt. Snow with hot tub and sauna.
West Dover, VT
7% off
Price is NZ$11,805
NZ$11,805
NZ$1,686 per night
includes taxes & fees
Image gallery for Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!
1010 out of 10 rating
Exceptional
(6 reviews)
Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!
Wilmington, VT
8% off
Price is NZ$12,707
NZ$12,707
NZ$1,815 per night
includes taxes & fees
Image gallery for Mount Snow Post and Beam House
1010 out of 10 rating
Exceptional
(38 reviews)
Mount Snow Post and Beam House
Wilmington, VT
16% off
Price is NZ$7,719
NZ$7,719
NZ$1,103 per night
includes taxes & fees
Image gallery for ❄️Chimney Hill. Mt. Snow ski home-Cozy Family home sleeps 6❄️
1010 out of 10 rating
Exceptional
(16 reviews)
❄️Chimney Hill. Mt. Snow ski home-Cozy Family home sleeps 6❄️
Wilmington, VT
12% off
Price is NZ$4,425
NZ$4,425
NZ$632 per night
includes taxes & fees
Image gallery for 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
9.69.6 out of 10 rating
Exceptional
(16 reviews)
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
West Dover, VT
7% off
Price is NZ$2,794
NZ$2,794
NZ$399 per night
includes taxes & fees
Image gallery for HotTub&GameRm&Traeger Smoker-Across from Golf, 5 min to Lake, 15 min 2 Mt Snow
1010 out of 10 rating
Exceptional
(5 reviews)
HotTub&GameRm&Traeger Smoker-Across from Golf, 5 min to Lake, 15 min 2 Mt Snow
Wilmington, VT
15% off
Price is NZ$4,818
NZ$4,818
NZ$688 per night
includes taxes & fees
Image gallery for Post and Beam Style house w/ Hot Tub - Minutes to Mt. Snow/Golf/Bars/Restaurants
1010 out of 10 rating
Exceptional
(10 reviews)
Post and Beam Style house w/ Hot Tub - Minutes to Mt. Snow/Golf/Bars/Restaurants
West Dover, VT
11% off
Price is NZ$6,280
NZ$6,280
NZ$897 per night
includes taxes & fees
Image gallery for Mount Snow Townhome w/ Heated Pool! - The Rooster
1010 out of 10 rating
Exceptional
(11 reviews)
Mount Snow Townhome w/ Heated Pool! - The Rooster
West Dover, VT
17% off
Price is NZ$2,852
NZ$2,852
NZ$407 per night
includes taxes & fees
Image gallery for Charming Chalet w. Hot Tub - 1 mile to Mt. Snow
1010 out of 10 rating
Exceptional
(11 reviews)
Charming Chalet w. Hot Tub - 1 mile to Mt. Snow
West Dover, VT
8% off
Price is NZ$5,878
NZ$5,878
NZ$840 per night
includes taxes & fees
Image gallery for Outdoor Enthusiasts Paradise in Beautiful Vermont!
1010 out of 10 rating
Exceptional
(13 reviews)
Outdoor Enthusiasts Paradise in Beautiful Vermont!
Wilmington, VT
6% off
Price is NZ$2,920
NZ$2,920
NZ$417 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in South Main Street
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Find the best place to stay - South Main Street
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Sleeps 32 · 12 bedrooms · 12 bathrooms
8.88.8 out of 10
Excellentexcellent
43 reviews(43 reviews)
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Sleeps 3 · 2 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
49 reviews(49 reviews)
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Beautiful Lodging at Mount Snow with Hot Tub on Deck
Sleeps 12 · 4 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
40 reviews(40 reviews)
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Sleeps 30 · 9 bedrooms · 4+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Sleeps 6 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value