Photo by William E Berry Jr.

Holiday Homes in Windsor

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Featured Holiday Homes in Windsor

New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b
Terrace/patio

New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b

10.0 out of 10, Exceptional, (40)
"The owner was extremely easy to work with and even more responsive. The house has an AMAZING view Killington. Very clean and once you get the cast iron stove to temp it worked really well to heat the house. The sauna, and foosball table worked well. The hotub was easy to use, it fits 3 full size adults with no issue. The kitchen fridge had plenty of condiments, dressing and sauces. A really nice treat was that the beverage fridge was stocked with prev renters' drinks as well we added to it for...
New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola
Outdoor dining

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
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
Property map

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

9.2 out of 10, Wonderful, (31)
"Clean house and glad we were able to bring our dog. Close to so many great mountains and rivers to explore. Great shower pressure. Wish there were some picnic tables or outdoor eating spaces on the sunny property."
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
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, (63)
"This house was perfect for our group of twelve. We were three families with kids ranging in ages from 6-14yrs old. There was enough space for everyone to relax after a day of skiing. The kitchen was very well stocked and had everything we needed. The ski hill is only a 5 mins drive. We would definitely stay here again"
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Fridge, microwave, oven, stovetop

BruinsDen - Ski On Ski Off (Home Stretch Trail)

9.8 out of 10, Exceptional, (9)
"My family and I stayed for a week at this home. The pictures do not do this home justice! It was very clean, well equipped with everything we needed and very spacious. The beds were really comfortable, showers were really nice and everything was stocked with all the essentials. We cooked breakfast every morning and dinner a few evenings and had everything we needed. Check in process was easy and all the details were clearly defined for checkout (also easy). The property is nice and private with...
The price is AU$1,089
includes taxes & fees
2 Dec - 3 Dec
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Outdoor dining

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
Spectacular opportunity to enjoy the finest property in Killington Summit
Interior

Spectacular opportunity to enjoy the finest property in Killington Summit

9.4 out of 10, Exceptional, (19)
"We had a group of old friends that together for the weekend. The house was gorgeous, had a ton of room and was a lot of fun. Just a very warm, fun and relaxing place to be. There are a number of spaces that are great for gathering and plenty of awesome amenities and games for fun. "
Spectacular opportunity to enjoy the finest property in Killington Summit
S'Mookie the Bear- ski on and off, hot tub, pool
Smart TV, fireplace, stereo

S'Mookie the Bear- ski on and off, hot tub, pool

9.0 out of 10, Wonderful, (2)
"Wonderful four bedroom place that fit our family well. Very well stocked for cooking. Easy walk to ski in/ ski out."
S'Mookie the Bear- ski on and off, hot tub, pool
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen
Smart TV, fireplace, books

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!
Exterior

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
Exterior

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
Smart TV, fireplace, books

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
Fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

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$580
includes taxes & fees
2 Dec - 3 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
Smart TV, fireplace

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
Ski-in/out sunrise condo with pool & hot tub - great ski retreat
Fridge, microwave, oven, stovetop

Ski-in/out sunrise condo with pool & hot tub - great ski retreat

9.0 out of 10, Wonderful, (78)
"Property was nice and location was great even for an of season stay. Lots of fun close by like the killington adventure center & visiting small toes like Woodstock & ludlow. Also hiking close by!! We were a bit disappointed that the indoor pool & hot tub were closed until the peak winter season so may mention that in the listing. We loved having the fire place & sauna inside unit. "
Ski-in/out sunrise condo with pool & hot tub - great ski retreat
Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table
Property grounds

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
Outdoor spa tub

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
Chic Farmhouse Decor | Deck w/View
Fridge, microwave, oven, stovetop

Chic Farmhouse Decor | Deck w/View

10.0 out of 10, Exceptional, (46)
"Interior, comfort, everything we needed - house had it. Location is super cool aswell. Welcome bottle of red wine was a nice surprise !:)"
The price is AU$626
includes taxes & fees
1 Dec - 2 Dec
Chic Farmhouse Decor | Deck w/View
Tranquil home in a quiet neighborhood with easy access to outdoor fun
Fridge, microwave, oven, stovetop

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
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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Other property types in Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (39)
"Amazing house great price but note that there are only two split units cooling down the house which means one bed room only gets ac if the other bedrooms split unit is on and both doors are open"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor dining

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (196)
"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Beautiful Myrtle Beach Condo with Amenities Galore
Beach nearby

Beautiful Myrtle Beach Condo with Amenities Galore

8.8 out of 10, Excellent, (161)
"This was a really nice spacious property. It was very clean and in a nice location. "
Beautiful Myrtle Beach Condo with Amenities Galore
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.
Beautiful view of the beach with palm trees

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