Holiday Homes in Windsor County

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Featured Holiday Homes in Windsor County

Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

9.8 out of 10, Exceptional, (17)
"This is a beautiful property with beautiful views, lots of indoor and outdoor space for the little ones to play, and for the adults to chill and socialize. Very clean and well kept. We would love to come back and stay here again in the future!"
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

8.8 out of 10, Excellent, (18)
"Very cute cabin in the woods. Less than 2 miles off of route 4, which made it easy to get anywhere in Vermont!"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen

9.8 out of 10, Exceptional, (21)
"Everything was clean and comfortable and had a great view from the living room/primary bedroom. Because we were there for a wedding we didn't use the kitchen or really get to enjoy all the amenities but the proximity to Woodstock was an added bonus. The shower head in the shared bathroom could use updating but really that's a small complaint. All in all we had a great stay."
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen

Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!

2.0 star property
10.0 out of 10, Exceptional, (2)
"Had a nice stay with friends at this beautiful house. Very spacious with plenty of beds and bathrooms. Spacious and very clean in quiet, peaceful location. Hosts quickly responded to any questions."
Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (83)
"A lovely, cozy spot in historic Quechee. The hosts have thoughtfully designed the experience in every way - definitely a property I will stay at again when I am in the area!"
Beautifully renovated with fireplace and coffee bar

Custom-built Tiny House on forested lot near Quechee

10.0 out of 10, Exceptional, (48)
"Everything was perfect and as advertised. Very easy to communicate with owner. No issues and offered a very private relaxing getaway. You’ll love it. Worth every penny. "
Custom-built Tiny House on forested lot near Quechee

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

9.8 out of 10, Exceptional, (88)
"Very comfortable home. Loved the nostalgic feeling "
The price is AU$544
includes taxes & fees
3 Dec - 4 Dec
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Slopeside townhome on Okemo Ski Mountain! Summer Pool, Tennis & Air Conditioning

10.0 out of 10, Exceptional, (21)
"Great property, there was everything that we needed for our weekend getaway."
Slopeside townhome on Okemo Ski Mountain! Summer Pool, Tennis & Air Conditioning

Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table

9.8 out of 10, Exceptional, (99)
"Nice, private and relaxing cabin in a great location on the mountain. Would definitely recommend and rent again "
Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table

Base Lodge - shuttle rte in winter - 10 BR, 5 Bath, Slp 34

9.8 out of 10, Exceptional, (75)
"We have a group which tries to get away to Vermont once a year. This was actually our second stay at the Base Lodge (first was in 2022). The property has plentiful accommodation and a great interior space just a short walk from central Ludlow. We also appreciate the quiet back yard amenities at the Lodge. The owners were very responsive during our stay, answering questions promptly and keeping track of our needs. We would definitely stay again. "
Base Lodge - shuttle rte in winter - 10 BR, 5 Bath, Slp 34

Tranquil home in a quiet neighborhood with easy access to outdoor fun

9.4 out of 10, Exceptional, (49)
"Great property. We especially enjoyed the view of the mountain! The only thing I would recommend is to mark the entrance better if possible. Hard to see at night. Otherwise, a lovely visit. Strongly recommended. "
Tranquil home in a quiet neighborhood with easy access to outdoor fun

Luxurious, Secluded, Ski Chalet, w/ Country Decor & Hot Tub Near Okemo

10.0 out of 10, Exceptional, (142)
"A great secluded place to stay. Excellent communication with us. Accommodated our schedule. Was perfect for our grandchildren to be with us also. Would definitely return. Very clean. Everything we needed was available for use. "
Luxurious, Secluded, Ski Chalet, w/ Country Decor & Hot Tub Near Okemo

Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE

9.8 out of 10, Exceptional, (91)
"Great weekend! Don't be deceived by your first impression when pulling in. This home is huge ! The setting is private and quiet. Two family rooms provide space for younger ones. Large dining room table is great for meals and games. Kitchen is well equipped. Usable outdoor space is small but a large patio is located next to the woods and has a large hot tub, table that seats 6 , firepit, and a gas grill. This is where we spent our evenings."
Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE

Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee

9.4 out of 10, Exceptional, (41)
"Lovely place to enjoy Vermont. The condo was well located, clean, and the quechee club amenities were a lot of fun."
Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee

Sweet chalet with private hot tub, firepit, game room & minibar

9.6 out of 10, Exceptional, (35)
"All good lots of fun"
Sweet chalet with private hot tub, firepit, game room & minibar

Killington ski house

9.6 out of 10, Exceptional, (31)
"Great place, great location, great response and communication with the host, Dean. Very much appreciated. "
Killington ski house

Tranquility awaits for your stay at our cherished log home on 6 secluded acres.

10.0 out of 10, Exceptional, (1)
"It was such an nice house in a great part of VT. The owners were super helpful and the property is stunning. Perfect for a couple of days. We're already planning our trip back!"
Tranquility awaits for your stay at our cherished log home on 6 secluded acres.

BRAND NEW 8 Bedroom House/On Shuttle Route/Walk to Downtown /Minutes to Okemo

2.0 star property
BRAND NEW 8 Bedroom House/On Shuttle Route/Walk to Downtown /Minutes to Okemo

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

8.2 out of 10, Very good, (33)
"All in all it was a great trip. The place was very cute and as described. The upstairs bedrooms are not for light sleepers as the walls only go so far up so they are not really divided. I had read this in other reveiws but honestly for us it wasn't a problem. We went as a family group and it was kind of nice to be able to lay in bed and talk to the others in the room next to you. When we got there the hot tub was so hot that we were not able to get in. Maybe a problem with the thermostat but...
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
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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