Vacation Rentals in Windsor County

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Top Vacation Rentals in Windsor County

Winterplace at Okemo
Property grounds

Winterplace at Okemo

4.0 star property
8.8 out of 10, Excellent, (24)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "
Winterplace at Okemo
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Fridge, microwave, oven, stovetop

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

8.0 out of 10, Very Good, (41)
"This place was great for my family and I. It is very close to Okemo and town "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Exterior

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (176)
"Gorgeous log home , spacious, cozy , fun and comfortable ."
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Exterior

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

9.8 out of 10, Exceptional, (126)
"Terrific and comfortable place to stay! Amazing firepit!"
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Vermont Retreat
Fridge, microwave, oven, stovetop

Vermont Retreat

10.0 out of 10, Exceptional, (26)
"Lovely banana bread greeted me when I arrived and there was fresh milk and orange juice as well. A bit off the beaten track, but a lovely one bedroom apartment just right for a weekend in Vermont. "
Vermont Retreat
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

9.0 out of 10, Wonderful, (72)
"Perfect location for a quick ski trip. "
The price is ￥11,078
￥36,651 total
includes taxes & fees
Sep 29 - Sep 30
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Interior

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

2.0 star property
10.0 out of 10, Exceptional, (7)
"Very relaxing stay! Cabins are beautiful, location is private and Wendi was very helpful with our stay"
The price is ￥28,508
￥49,459 total
includes taxes & fees
Oct 22 - Oct 23
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Idyllic Lakefront House Suited Two Families
Property grounds

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (166)
"We really enjoyed our stay at the lake house. We had great views of the lake and the kitchen was very well stocked. The beds were comfortable and the house was very clean and nicely decorated. Thank you for the incredible stay and we will be staying again!"
Idyllic Lakefront House Suited Two Families
Treehouse at Wise Pines- SoBo
Property grounds

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (21)
"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"
The price is ￥29,542
￥36,998 total
includes taxes & fees
Sep 24 - Sep 25
Treehouse at Wise Pines- SoBo
Fireplace, Game Room, Corner Condo - Sugar Hill 3E
Fridge, microwave, oven, stovetop

Fireplace, Game Room, Corner Condo - Sugar Hill 3E

6.0 out of 10, (1)
Fireplace, Game Room, Corner Condo - Sugar Hill 3E
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi
TV, fireplace

Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

10.0 out of 10, Exceptional, (6)
"Lovely rustic and cozy cabin stay"
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi
Nana's House
Exterior detail

Nana's House

10.0 out of 10, Exceptional, (43)
"I'm not much for reviews, but everything about this place was perfect! We can't wait to go back!"
Nana's House
Amazing home on 90 acres - AC, fireplace & great mountain views
Fridge, microwave, oven, stovetop

Amazing home on 90 acres - AC, fireplace & great mountain views

9.0 out of 10, Wonderful, (43)
"Was good older log cabin with decent amenities. Everything worked. family was comfortable. nice area."
Amazing home on 90 acres - AC, fireplace & great mountain views
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Terrace/patio

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

2.0 star property
9.8 out of 10, Exceptional, (77)
"The feel was so relaxing, felt like home.Im at a loss for words was just wonderful."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Converted Carriage Barn - The Carriage House Unit1
Dining

Converted Carriage Barn - The Carriage House Unit1

9.8 out of 10, Exceptional, (22)
" Very nice and quiet location. Close to various restaurants. Enjoyed our stay!"
Converted Carriage Barn - The Carriage House Unit1
Perfect Woodstock Getaway! Lovely Riverside Home
Fridge, microwave, oven, stovetop

Perfect Woodstock Getaway! Lovely Riverside Home

9.8 out of 10, Exceptional, (8)
"We had a wonderful weekend at Charlie's house. The property was clean and welcoming and the fenced in backyard was excellent for our dog Riley"
Perfect Woodstock Getaway! Lovely Riverside Home
🌺Luxury Estate🌳 25 Gorgeous Acres of Privacy 🌳Family Getaway🌳Swimming Pond🌺
Exterior

🌺Luxury Estate🌳 25 Gorgeous Acres of Privacy 🌳Family Getaway🌳Swimming Pond🌺

9.8 out of 10, Exceptional, (15)
"The Property and surrounding country were spectacular and me and my family and our pets had a lovely time. If you love the outdoors and staying in a wonderful home this is the place!"
🌺Luxury Estate🌳 25 Gorgeous Acres of Privacy 🌳Family Getaway🌳Swimming Pond🌺
Hawks Mountain Farm, full apartment on a working farm.
Property grounds

Hawks Mountain Farm, full apartment on a working farm.

9.8 out of 10, Exceptional, (42)
"Very nice place "
Hawks Mountain Farm, full apartment on a working farm.
BRIDGEWATER RETREAT
Exterior

BRIDGEWATER RETREAT

10.0 out of 10, Exceptional, (9)
"A true gem."
BRIDGEWATER RETREAT
Sunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village
Property grounds

Sunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village

10.0 out of 10, Exceptional, (94)
"Exceptional hosts; beautiful and peaceful property; everything we needed for a perfect adventure in Woodstock. We wouldn’t hesitate to stay here again!"
Sunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village
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

Kedron Valley Inn

Kedron Valley Inn

10/10 Excellent
"Kind and professional. "
Justin 2-night trip
Posted 10 hours ago
Kedron Valley Inn

Find out more about Windsor County

Find out more about Windsor County

Vacation Apartments in Windsor County

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