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Windsor County Holiday Rentals

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Our top choices for Windsor County holiday rentals

Interior

The Barn at Winterfound Farm with Valley Views

The Barn at Winterfound Farm with Valley Views
Woodstock
The price is HK$5,126
HK$12,810 total
includes taxes & fees
8 Jul - 9 Jul
The Barn at Winterfound Farm with Valley Views
Interior

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is HK$2,227
HK$3,505 total
includes taxes & fees
8 Jul - 9 Jul
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is HK$4,228
HK$7,871 total
includes taxes & fees
14 Jul - 15 Jul
Cozy Vermont Cabin · Mountain Views · Near Okemo
Indoor pool

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Okemo Village
10.0 out of 10, Exceptional, (64 reviews)
"The host is extremely friendly and accommodating! The place is large and didn’t feel cramped with two adults and five male teenagers! Perfect in every way, clean, well stocked, and easy access to the slopes!"
United States
Nina
The price is HK$3,529
HK$6,585 total
includes taxes & fees
8 Jul - 9 Jul
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Smart TV, fireplace, books

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Great location, "
United States
Bryan R J.
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Outdoor pool, a heated pool

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (23 reviews)
"Great location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "
United States
Ania H.
The price is HK$2,353
HK$4,260 total
includes taxes & fees
8 Jul - 9 Jul
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Interior

Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
10.0 out of 10, Exceptional, (12 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is HK$1,176
HK$2,029 total
includes taxes & fees
19 Jul - 20 Jul
Addie's Place: A Quiet and Quirky Guesthouse
Interior

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (20 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is HK$1,906
HK$3,100 total
includes taxes & fees
4 Aug - 5 Aug
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Hair dryer, towels, soap, shampoo

Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is HK$1,765
HK$4,752 total
includes taxes & fees
8 Jul - 9 Jul
Terrific 3-bedroom cottage with AC in charming Cavendish
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (87 reviews)
"Beautiful and immaculately clean home located within walking distance to downtown, shopping, and restaurants. Very quiet location. We felt safe and comfortable at this home. Property has 3 bedrooms and 5 very comfortable beds. The attic bedroom has 3 single beds which is handy for larger families. Loved sitting around the fire pit and was pleased that our yard was separated from the neighbors. Thank you so much for sharing your hospitality."
United States
Kristen
The price is HK$1,673
HK$3,440 total
includes taxes & fees
9 Jul - 10 Jul
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Dining

New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (17 reviews)
"Second time we have stayed here. Amazing home, amazing location. The flow and design makes us happy "
United States
karyn r.
The price is HK$2,103
HK$4,690 total
includes taxes & fees
9 Jul - 10 Jul
New Ludlow Village Home with Stunning Okemo Mountain View
Front of property

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is HK$9,333
HK$14,487 total
includes taxes & fees
8 Jul - 9 Jul
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Fridge, microwave, oven, stovetop

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (111 reviews)
"Clean great cozy place!"
United States
Himanshu P.
The price is HK$1,518
HK$3,229 total
includes taxes & fees
8 Jul - 9 Jul
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Terrace/patio

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (12 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is HK$1,412
HK$2,802 total
includes taxes & fees
30 Jul - 31 Jul
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Property grounds

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Ludlow
8.0 out of 10, Very good, (3 reviews)
"The cabin was very clean and offered everything we needed for our ski vacation! Access to the ski mountain was very close which was great! "
United States
Anne W.
The price is HK$1,796
HK$3,652 total
includes taxes & fees
8 Jul - 9 Jul
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Living area

Cozy Private Cabin in Andover - Fireplace & Hot tub

Cozy Private Cabin in Andover - Fireplace & Hot tub
Andover
The price is HK$1,795
HK$4,048 total
includes taxes & fees
8 Jul - 9 Jul
Cozy Private Cabin in Andover - Fireplace & Hot tub
Outdoor dining

Okemo | Studio Condo + Loft | Near Slopes + Pool

Okemo | Studio Condo + Loft | Near Slopes + Pool
Jackson Gore Base Area
10.0 out of 10, Exceptional, (2 reviews)
"Very conveinent check in, nice property."
United States
michael
The price is HK$1,643
HK$2,098 total
includes taxes & fees
8 Jul - 9 Jul
Okemo | Studio Condo + Loft | Near Slopes + Pool
Interior

The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle

The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle
Ludlow
10.0 out of 10, Exceptional, (1 review)
"Cute place right in town, super convenient to the mountain (although if you’re relying on the shuttle it’s only once an hour so can be annoying if you don’t time it well). Rooms comfortably slept 4 plus one on the sofa bed, annd everything was in good shape, Andrew and Jillian were great hosts!"
United States
Max R.
The price is HK$2,659
HK$6,020 total
includes taxes & fees
8 Jul - 9 Jul
The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle
Interior

180-degree panoramic views of Vermont's mountains from the living room and Deck

180-degree panoramic views of Vermont's mountains from the living room and Deck
Hartford
8.0 out of 10, Very good, (4 reviews)
"Plenty of room beautiful view"
United States
Anthony A.
The price is HK$2,209
HK$4,064 total
includes taxes & fees
8 Jul - 9 Jul
180-degree panoramic views of Vermont's mountains from the living room and Deck
Beach

Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
The price is HK$2,188
HK$4,084 total
includes taxes & fees
13 Jul - 14 Jul
Cabin on the hill Ascutney Vt - 4 bedrooms
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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Top Windsor County Hotel Reviews

The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

10/10 Excellent
"Everything was great but that bathtub is dangerously slick"
Cary 1-night trip
Posted 5 hours ago
The Quechee Inn at Marshland Farm