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8 Aug - 10 Aug
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29 Aug - 31 Aug
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26 Sep - 28 Sep

Vacation Homes in Windsor

Quaint lakefront home with a fire pit and beautiful views
Property grounds

Quaint lakefront home with a fire pit and beautiful views

9.4 out of 10, Exceptional, (96)
"We had a great time staying at this cabin. It’s really well located and was perfect for our stay."
Quaint lakefront home with a fire pit and beautiful views
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

8.2 out of 10, Very Good, (39)
"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
Pet-Friendly Claremont Vacation Rental!
Terrace/patio

Pet-Friendly Claremont Vacation Rental!

8.8 out of 10, Excellent, (5)
"Only will stay here! "
Pet-Friendly Claremont Vacation Rental!
Pet-Friendly, Heart of Quechee | Jay Hill Home
Fridge, microwave, oven, stovetop

Pet-Friendly, Heart of Quechee | Jay Hill Home

2.0 star property
9.4 out of 10, Exceptional, (3)
"Perfect house for the weekend. Clean. Nice location. Everything was as described. "
Pet-Friendly, Heart of Quechee | Jay Hill Home
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Interior

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

10.0 out of 10, Exceptional, (72)
"We absolutely LOVED our stay. The house and all its amenities were perfect for our ski trip, and we would be thrilled to come back again some time. "
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Deere Run townhouse with private sauna - pool & tennis - walk to Lake Pinneo
Fridge, microwave, oven, stovetop

Deere Run townhouse with private sauna - pool & tennis - walk to Lake Pinneo

9.0 out of 10, Wonderful, (24)
"We had a wonderful time in the condo. Clean, very accommodating - loved the fireplace!"
Deere Run townhouse with private sauna - pool & tennis - walk to Lake Pinneo
Ski-in/out home with a hot tub, fireplace, cable & golf nearby
Outdoor dining

Ski-in/out home with a hot tub, fireplace, cable & golf nearby

9.4 out of 10, Exceptional, (23)
"Nice and roomy. Plenty of room throughout the entire house. Kitchen area LARGE. back deck was nice with the hot tub. Ski run steps from the house. Really nice place."
Ski-in/out home with a hot tub, fireplace, cable & golf nearby
Beautifully renovated with fireplace and coffee bar
Smart TV, fireplace, books

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (112)
"Very cozy, great kitchen. The beds are extremely comfortable. The surrounding area is beautiful with plenty to do. Highly recommend."
Beautifully renovated with fireplace and coffee bar
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
Exterior

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

9.8 out of 10, Exceptional, (218)
"Our stay was amazing! The house offered everything we needed, was spacious and clean. Working with the owners was also easy. Would definitely recommend and stay again!"
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

9.6 out of 10, Exceptional, (121)
"Another fun time at this well located, well appointed home."
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking
Heated Saltwater Pool: Riverfront Home in Ludlow
A heated pool

Heated Saltwater Pool: Riverfront Home in Ludlow

10.0 out of 10, Exceptional, (12)
"We had a wonderful stay. The house was very clean and well maintained and very well stocked. The pool and surrounding area were beautiful. We enjoyed day hikes at buttermilk falls and echo lake, which are so close by. We highly recommend this place to anyone looking to spend a few relaxing days in Vermont."
Heated Saltwater Pool: Riverfront Home in Ludlow
Private! Sauna, 3BR/2Ba, Pet-Friendly | Twin Peaks
TV, offices

Private! Sauna, 3BR/2Ba, Pet-Friendly | Twin Peaks

9.2 out of 10, Wonderful, (12)
"We really enjoyed our stay in Quechee. The location is convenient. The accommodations were great; plenty of towels, toiletries provided in the bathrooms, extra sheets and blankets. It’s great having a dog friendly place to stay. We’ll definitely book again the next time we visit family in VT. "
Private! Sauna, 3BR/2Ba, Pet-Friendly | Twin Peaks
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
Fridge, microwave, oven, stovetop

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

9.6 out of 10, Exceptional, (25)
"Absolutely loved it!!! Amazing house. Will definitely stay again!"
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays
Exterior

NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays

10.0 out of 10, Exceptional, (36)
"Our annual trip was great! The house was fantastic and the owners were very friendly and responsive. Would definitely recommend this awesome house!"
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays
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, (75)
"Beautiful area and gorgeous leaves. Liked having a weber grill."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
Fridge, microwave, oven, stovetop

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

10.0 out of 10, Exceptional, (53)
"Cozy accommodations, great location, beautiful property, wonderful hosts."
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
Country townhome - mountain view - walk to Village of Quechee - near Club & golf
Pool

Country townhome - mountain view - walk to Village of Quechee - near Club & golf

9.0 out of 10, Wonderful, (34)
"Great location, cute condo, comfortable beds, modern kitchen."
Country townhome - mountain view - walk to Village of Quechee - near Club & golf
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Property grounds

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (25)
"Beautiful place."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Property grounds

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

9.8 out of 10, Exceptional, (212)
"Only a 4 minute drive from the slopes!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Quechee - Four Season Resort Townhome
Living area

Quechee - Four Season Resort Townhome

10.0 out of 10, Exceptional, (8)
"Very nice ski chalet with great kitchen, large and private bedrooms and a hot tub. Very suitable for a small family retreat."
Quechee - Four Season Resort Townhome
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 Hotel Reviews

Courtyard by Marriott Hanover Lebanon

Courtyard by Marriott Hanover Lebanon

10/10 Excellent
"The staff was very friendly and helpful. The room was nice and clean. Comfy beds. Breakfast was good and fast."
Melanie 1-night trip
Posted 1 day ago
Courtyard by Marriott Hanover Lebanon