Photo by William E Berry Jr.

Holiday Homes in Windsor

    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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Featured Holiday Homes in Windsor

Our top choices for Windsor holiday homes

Sleep Woodstock - 2 Double Beds - Dog Friendly

10.0 out of 10, Exceptional, (2)
"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 AU$297
includes taxes & fees
24 Aug - 25 Aug
Sleep Woodstock - 2 Double Beds - Dog Friendly

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 AU$314
includes taxes & fees
24 Aug - 25 Aug
Studio Suite #4 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

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

Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington

Sleep Woodstock - Dog Friendly King Suite

10.0 out of 10, Exceptional, (1)
"We had an excellent stay, everything was so clean, the room was well appointed and there was even a little communal area with laundry, kitchen, snacks, and shuffleboard. We would absolutely recommend this motel, it’s a gem! "
The price is AU$316
includes taxes & fees
4 Sept - 5 Sept
Sleep Woodstock - Dog Friendly King Suite

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 AU$652
includes taxes & fees
9 Sept - 10 Sept
Lake Front Family Friendly Escape

@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 AU$862
includes taxes & fees
4 Sept - 5 Sept
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

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

10.0 out of 10, Exceptional, (4)
"Beautiful views"
The price is AU$334
includes taxes & fees
21 Sept - 22 Sept
Studio Suite #3 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

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 AU$670
includes taxes & fees
25 Aug - 26 Aug
The Grizz- AC, Pool, Sauna, Gym, Near Resort

Charming Cavendish Guesthouse NEW SAUNA SEPT 2025!

9.8 out of 10, Exceptional, (7)
"Very cozy and had all the essentials we needed for our trip! Check in and check out were easy, and it was perfect for our winter trip. It's a short drive to Okemo, which is super convenient - would definitely stay here again!"
The price is AU$437
includes taxes & fees
25 Aug - 26 Aug
Charming Cavendish Guesthouse NEW SAUNA SEPT 2025!

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

9.4 out of 10, Exceptional, (16)
"We celebrated my sister's 80th birthday at Blueberry Hill. It was very quiet, pleasant and perfect for our family."
The price is AU$862
includes taxes & fees
2 Sept - 3 Sept
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

10.0 out of 10, Exceptional, (1)
"Beautiful, spacious, clean, relaxing home and property. Loved it! Would stay here again."
The price is AU$735
includes taxes & fees
21 Sept - 22 Sept
Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

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."
Two Queen Bed Standard Hotel room with outdoor heated pool 201

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 AU$1,047
includes taxes & fees
4 Sept - 5 Sept
Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee

Acres & Views! Firepit, BBQ | Bayley Way Getaway

The price is AU$1,022
includes taxes & fees
25 Aug - 26 Aug
Acres & Views! Firepit, BBQ | Bayley Way Getaway

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 AU$706
includes taxes & fees
8 Sept - 9 Sept
Chic Farmhouse Decor | Deck w/View

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 AU$243
includes taxes & fees
1 Sept - 2 Sept
Whimsical Room & Private Bathroom in Historic Inn

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 AU$1,047
includes taxes & fees
26 Aug - 27 Aug
Hot Tub | Firepit | Dog-Friendly | Golf | Foliage

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

Sleep Woodstock Mobility Impaired Accessible Suite

The price is AU$242
includes taxes & fees
25 Aug - 26 Aug
Sleep Woodstock Mobility Impaired Accessible Suite
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

Top Windsor Hotel Reviews