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Check prices for these dates

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Aug 29 - Aug 31
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Sep 5 - Sep 7
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Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Vacation Homes in Windsor

Our top choices for Windsor vacation homes

Two Queen Bed Standard Hotel room with outdoor heated pool 201
TV, books, offices

Two Queen Bed Standard Hotel room with outdoor heated pool 201

8.6 out of 10, Excellent, (12)
"Our room was easy to find and very clean. And the late check-in was very helpful."
The price is ￥15,375
￥23,282 total
includes taxes & fees
Aug 24 - Aug 25
Two Queen Bed Standard Hotel room with outdoor heated pool 201
Sleep Woodstock - 2 Double Beds - Dog Friendly
Iron/ironing board, travel crib, WiFi, bed sheets

Sleep Woodstock - 2 Double Beds - Dog Friendly

10.0 out of 10, Exceptional, (1)
"The property is exactly as represented. It’s super clean. Comfortable beds. Bathrooms are updated and nice. It’s right across from a beautiful river and close proximity to quaint downtown Woodstock or nearby Killington. Felt safe and homey. Great communication from property owner. Would recommend! "
The price is ￥19,994
￥28,098 total
includes taxes & fees
Sep 2 - Sep 3
Sleep Woodstock - 2 Double Beds - Dog Friendly
Studio Suite #4 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee
Dining

Studio Suite #4 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

10.0 out of 10, Exceptional, (12)
"What a great place to stay at Sunapee. Great location, amenities, clean and what a view! Thank you to the hosts :)"
The price is ￥31,949
￥39,158 total
includes taxes & fees
Aug 21 - Aug 22
Studio Suite #4 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
Exterior

107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool

8.0 out of 10, Very Good, (6)
"The check in process was so easy, our room was clean and had everything we needed. We would definitely stay here again"
The price is ￥16,928
￥25,097 total
includes taxes & fees
Sep 7 - Sep 8
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
Fridge, microwave, oven, stovetop

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

2.0 star property
10.0 out of 10, Exceptional, (1)
"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "
The price is ￥25,219
￥80,400 total
includes taxes & fees
Aug 21 - Aug 22
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
The Grizz- AC, Pool, Sauna, Gym, Near Resort
Golf

The Grizz- AC, Pool, Sauna, Gym, Near Resort

10.0 out of 10, Exceptional, (4)
"Place was overall great and just as advertised. Beds were awesome including the Murphy bed. Thanks for a wonderful weekend! I would definitely stay again. "
The price is ￥15,176
￥63,112 total
includes taxes & fees
Aug 21 - Aug 22
The Grizz- AC, Pool, Sauna, Gym, Near Resort
Lake Front Family Friendly Escape
Fridge, microwave, oven, stovetop

Lake Front Family Friendly Escape

10.0 out of 10, Exceptional, (3)
"What an amazing place! Very serene, clean and big enough for my family of 5. The hosts thought of everything to make our stay comfortable and memorable. Tough to beat the location! We will absolutely return!"
The price is ￥23,814
￥61,305 total
includes taxes & fees
Sep 8 - Sep 9
Lake Front Family Friendly Escape
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Dining

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

2.0 star property
10.0 out of 10, Exceptional, (13)
"Great place, great host, great location!"
The price is ￥23,666
￥74,143 total
includes taxes & fees
Sep 16 - Sep 17
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Studio Suite #3 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee
Property grounds

Studio Suite #3 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

10.0 out of 10, Exceptional, (4)
"Beautiful views"
The price is ￥31,949
￥38,356 total
includes taxes & fees
Sep 16 - Sep 17
Studio Suite #3 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee
Luxury Condo Tucked in the Heart of Killington
Fridge, microwave, oven, stovetop

Luxury Condo Tucked in the Heart of Killington

The price is ￥15,389
￥45,271 total
includes taxes & fees
Sep 17 - Sep 18
Luxury Condo Tucked in the Heart of Killington
Okemo's Back Room - in the heart of the village on the shuttle route!
Interior

Okemo's Back Room - in the heart of the village on the shuttle route!

9.6 out of 10, Exceptional, (14)
"Perfect location. Charming place to stay. Very clean. Great view of the creek."
The price is ￥19,228
￥53,484 total
includes taxes & fees
Aug 21 - Aug 22
Okemo's Back Room - in the heart of the village on the shuttle route!
Hot Tub | Firepit | Dog-Friendly | Golf | Foliage
Outdoor spa tub

Hot Tub | Firepit | Dog-Friendly | Golf | Foliage

8.0 out of 10, Very Good, (1)
"Place was nice a cozy. Had a minor issue that was communicated quickly and resolved."
The price is ￥30,469
￥98,444 total
includes taxes & fees
Aug 24 - Aug 25
Hot Tub | Firepit | Dog-Friendly | Golf | Foliage
Breakaway House: Renovated Killington Duplex, Unit A. Close to Resort.
Fridge, microwave, oven, stovetop

Breakaway House: Renovated Killington Duplex, Unit A. Close to Resort.

7.6 out of 10, Good, (4)
"Great location, clean and quiet."
The price is ￥21,639
￥67,717 total
includes taxes & fees
Aug 21 - Aug 22
Breakaway House: Renovated Killington Duplex, Unit A. Close to Resort.
The Carol - 10 minutes to Okemo & Newly Renovated- NEW SAUNA SEPT 2025!
Fridge, microwave, oven, stovetop

The Carol - 10 minutes to Okemo & Newly Renovated- NEW SAUNA SEPT 2025!

10.0 out of 10, Exceptional, (6)
"Check in and check out were incredibly easy, house decor was eclectic upscale, beds were super comfortable. Thank you Chris! Would definitely stay here again"
The price is ￥26,358
￥47,579 total
includes taxes & fees
Sep 2 - Sep 3
The Carol - 10 minutes to Okemo & Newly Renovated- NEW SAUNA SEPT 2025!
Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington
Outdoor spa tub

Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

9.2 out of 10, Wonderful, (5)
"Cute & functional 3 BR house. Was great for our spring skiing trip at Killington. "
The price is ￥23,754
￥72,643 total
includes taxes & fees
Aug 21 - Aug 22
Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington
Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee
Smart TV, video games, books

Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee

9.4 out of 10, Exceptional, (3)
"Walk to the harbor clean roomy house"
The price is ￥51,664
￥99,298 total
includes taxes & fees
Sep 3 - Sep 4
Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee
Whimsical Room & Private Bathroom in Historic Inn
Interior

Whimsical Room & Private Bathroom in Historic Inn

8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
The price is ￥13,137
￥22,980 total
includes taxes & fees
Sep 3 - Sep 4
Whimsical Room & Private Bathroom in Historic Inn
Chic Farmhouse Decor | Deck w/View
Fridge, microwave, oven, stovetop

Chic Farmhouse Decor | Deck w/View

10.0 out of 10, Exceptional, (51)
"Great cabin about 2 minutes from Mt. Sunapee resort and state park, as well as several lake towns. Beds are extra comfortable and the kitchen has everything we needed. "
The price is ￥32,688
￥67,725 total
includes taxes & fees
Sep 9 - Sep 10
Chic Farmhouse Decor | Deck w/View
Main Street Retreat 4-bedroom w Hot Tub, Walk to Beach, Harbor & Restaurants
Fridge, microwave, oven, stovetop

Main Street Retreat 4-bedroom w Hot Tub, Walk to Beach, Harbor & Restaurants

10.0 out of 10, Exceptional, (2)
"Great location. Fun weekend. House nicely maintained and supplied. "
The price is ￥47,235
￥111,950 total
includes taxes & fees
Sep 3 - Sep 4
Main Street Retreat 4-bedroom w Hot Tub, Walk to Beach, Harbor & Restaurants
BruinsDen- Hot Tub, Foosball, Mountain Views
Fridge, microwave, oven, stovetop

BruinsDen- Hot Tub, Foosball, Mountain Views

9.6 out of 10, Exceptional, (14)
"Great house. Had a wonderful stay. Not easy to directly access trails when adjacent trail is closed. It requires a longer hike. But this would be easier in peak season. Hot tub is a plus at the end of a ski day. "
The price is ￥30,351
￥106,500 total
includes taxes & fees
Aug 21 - Aug 22
BruinsDen- Hot Tub, Foosball, Mountain Views
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

Mountain Sports Inn

Mountain Sports Inn

10/10 Excellent
"This is the 2nd time we stayed here and it's a cute little place. It looks clean and the fresh air is great when you step outside. It does look a little older but nothing that bothers us at all. It had exactly what we needed and would definitely come back again."
David 2-night trip
Posted 1 day ago
Mountain Sports Inn