Photo by William E Berry Jr.

Windsor Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Browse Select 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 CA $144
CA $218 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 CA $188
CA $264 total
includes taxes & fees
Aug 24 - Aug 25
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 CA $258
CA $316 total
includes taxes & fees
Aug 24 - Aug 25
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 CA $159
CA $235 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 CA $236
CA $754 total
includes taxes & fees
Aug 24 - Aug 25
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 CA $142
CA $595 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $230
CA $582 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 CA $236
CA $712 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 CA $297
CA $357 total
includes taxes & fees
Sep 14 - Sep 15
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 CA $127
CA $405 total
includes taxes & fees
Sep 9 - Sep 10
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 CA $200
CA $524 total
includes taxes & fees
Aug 25 - Aug 26
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 CA $286
CA $917 total
includes taxes & fees
Sep 3 - Sep 4
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."
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 CA $221
CA $415 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 CA $233
CA $697 total
includes taxes & fees
Aug 24 - Aug 25
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 CA $485
CA $945 total
includes taxes & fees
Aug 27 - Aug 28
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 CA $123
CA $216 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $306
CA $635 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 CA $444
CA $1,064 total
includes taxes & fees
Sep 14 - Sep 15
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 CA $307
CA $1,039 total
includes taxes & fees
Aug 25 - Aug 26
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

10/10 Excellent
"My recent stay exceeded my expectations regarding hotel room prices, comfort of the bed and pillows, large breakfast and hot shower. Unfortunately most staff were not very friendly or accommodating minus the one sweet girl at the front desk who was able to allow us a late checkout time. "
Anonymous traveller 1-night trip
Posted 11 hours ago
Fireside Inn & Suites West Lebanon