Windsor Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Windsor vacation rentals

Exterior detail
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Peterborough
9.8 out of 10, Exceptional, (30)
"Fully equipped kitchen, comfortable open floor plan, easy walk to downtown and very hospitable—thank you—we’d like to stay here again next year!"
United States
Mark
The price is ￥11,291
￥24,161 total
includes taxes & fees
Dec 13 - Dec 14
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Comfort Townhome | In-room dining
Brook Road Condo

Brook Road Condo

Brook Road Condo
3.0 star property
Goshen
8.8 out of 10, Excellent, (3)
"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."
United States
Margaret
The price is ￥26,787
￥44,610 total
includes taxes & fees
Dec 22 - Dec 23
Brook Road Condo
Terrace/patio
Private Hot Tub Suite

Private Hot Tub Suite

Private Hot Tub Suite
Antrim
9.0 out of 10, Wonderful, (10)
"Stayed 3 nights while visiting relatives. Teen loved the Xbox. Had everything we could possibly need. Would definitely stay again."
United States
Dena S.
The price is ￥20,885
￥39,896 total
includes taxes & fees
Dec 23 - Dec 24
Private Hot Tub Suite
Smart TV, fireplace, video games, table tennis
Relaxing Hot Tub Getaway

Relaxing Hot Tub Getaway

Relaxing Hot Tub Getaway
Antrim
9.6 out of 10, Exceptional, (15)
"The hot tub was great and the peace and quiet was very nice."
United States
Brian B.
The price is ￥20,885
￥39,896 total
includes taxes & fees
Dec 14 - Dec 15
Relaxing Hot Tub Getaway
Property grounds
Lake Front Family Friendly Escape

Lake Front Family Friendly Escape

Lake Front Family Friendly Escape
Newport
10.0 out of 10, Exceptional, (4)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
The price is ￥19,759
￥55,299 total
includes taxes & fees
Dec 14 - Dec 15
Lake Front Family Friendly Escape
TV, fireplace, books
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

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

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
2.0 star property
Sunapee
10.0 out of 10, Exceptional, (18)
"Great home. The hosts were accessible and responded quickly to questions. Definitely will stay there again!"
United States
Ellen V.
The price is ￥26,816
￥70,953 total
includes taxes & fees
Dec 15 - Dec 16
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Beach
Book your ski vacations for the upcoming season.

Book your ski vacations for the upcoming season.

Book your ski vacations for the upcoming season.
Sutton
10.0 out of 10, Exceptional, (9)
"House is very clean and comfortable. Kitchen well appointed, Nice location with view of Blaisdell Lake. Several state parks and Lake Sunapee nearby"
United States
Nancy B.
The price is ￥25,230
￥60,326 total
includes taxes & fees
Dec 19 - Dec 20
Book your ski vacations for the upcoming season.
Terrace/patio
16 ppl 2 hot tubs, game room, fire pit

16 ppl 2 hot tubs, game room, fire pit

16 ppl 2 hot tubs, game room, fire pit
Antrim
9.8 out of 10, Exceptional, (9)
"Clean, lots of space, helpful host, hot tub was also nice"
United States
Howard H.
The price is ￥28,933
￥64,232 total
includes taxes & fees
Dec 14 - Dec 15
16 ppl 2 hot tubs, game room, fire pit
Interior
Charming cabin in delightful Greenfield New Hampshire with WiFi access

Charming cabin in delightful Greenfield New Hampshire with WiFi access

Charming cabin in delightful Greenfield New Hampshire with WiFi access
Greenfield
9.8 out of 10, Exceptional, (9)
"Its was great clean, quite and comfortable. "
United States
John G.
The price is ￥28,812
￥41,063 total
includes taxes & fees
Dec 20 - Dec 21
Charming cabin in delightful Greenfield New Hampshire with WiFi access
Property grounds
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Newbury
10.0 out of 10, Exceptional, (16)
"Loved staying at this quaint cottage, the outside spaces were lovely and it was very clean! Communication with the owner was seamless and they were fantastic to deal with. I would highly recommend a stay here! "
United States
Lisa P.
The price is ￥29,435
￥70,297 total
includes taxes & fees
Dec 16 - Dec 17
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
TV
Brook Road Cabin

Brook Road Cabin

Brook Road Cabin
Goshen
9.8 out of 10, Exceptional, (17)
"Would go back!"
United States
Elizabeth C.
The price is ￥25,074
￥48,667 total
includes taxes & fees
Dec 14 - Dec 15
Brook Road Cabin
Family Cabin, 2 Bedrooms, Mountain View | Living room | 40-inch Smart TV with cable channels, TV, Netflix
Brook Road Cabin

Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.8 out of 10, Good, (9)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
Brook Road Cabin
Property grounds
Unique Cozy private 1-bedroom apartment in charming Temple

Unique Cozy private 1-bedroom apartment in charming Temple

Unique Cozy private 1-bedroom apartment in charming Temple
Temple
9.8 out of 10, Exceptional, (7)
"very clean, well decorated, comfortable and peaceful"
United States
Dan G.
The price is ￥54,509
￥66,747 total
includes taxes & fees
Dec 16 - Dec 17
Unique Cozy private 1-bedroom apartment in charming Temple
Exterior
Room 10 - Queen Room

Room 10 - Queen Room

Room 10 - Queen Room
Francestown
10.0 out of 10, Exceptional, (1)
"Easy access to skiing Crotched mountain, great breakfast and dinner! Lovely people!"
United States
j l.
The price is ￥35,805
￥44,425 total
includes taxes & fees
Dec 23 - Dec 24
Room 10 - Queen Room
Fridge, microwave, oven, stovetop
Boutique Cottage | Patio & Fire Pit | Deck w/ View

Boutique Cottage | Patio & Fire Pit | Deck w/ View

Boutique Cottage | Patio & Fire Pit | Deck w/ View
New London
10.0 out of 10, Exceptional, (103)
"Lovely home. Very clean and nicely renovated. Will stay again when back in the area!"
United States
Cheryl S.
The price is ￥86,094
￥150,414 total
includes taxes & fees
Dec 19 - Dec 20
Boutique Cottage | Patio & Fire Pit | Deck w/ View
Exterior
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (1)
"Place was clean, cozy & very relaxing.. accommodating & communicative host provided us with necessary info for great week! Beautiful lake & landscape was great viewing during surprise snowstorm! Our Thanksgiving week was wonderful as we enjoyed lovely, quiet area in spacious 4 bdrm/2 bath home! Will definitely consider returning"
United States
Jeannie M.
The price is ￥31,756
￥72,399 total
includes taxes & fees
Dec 13 - Dec 14
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Outdoor spa tub
Downtown Hot Tub Escape

Downtown Hot Tub Escape

Downtown Hot Tub Escape
Keene
9.6 out of 10, Exceptional, (21)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
The price is ￥19,861
￥43,500 total
includes taxes & fees
Dec 14 - Dec 15
Downtown Hot Tub Escape
Property grounds
Unique Treehouse Near Mt Sunapee – No Cleaning Fee

Unique Treehouse Near Mt Sunapee – No Cleaning Fee

Unique Treehouse Near Mt Sunapee – No Cleaning Fee
Newbury
10.0 out of 10, Exceptional, (26)
"Great stay. Had a wonderful time."
United States
Chris P.
The price is ￥38,107
￥71,124 total
includes taxes & fees
Dec 14 - Dec 15
Unique Treehouse Near Mt Sunapee – No Cleaning Fee
TV, fireplace, DVD player, books
“Big Red” @ New London/Sunapee | Lake-Ski-Wellness

“Big Red” @ New London/Sunapee | Lake-Ski-Wellness

“Big Red” @ New London/Sunapee | Lake-Ski-Wellness
New London
10.0 out of 10, Exceptional, (14)
"Something for everyone! Not only will we be returning, but highly recommend! "
United States
Hillary N.
The price is ￥54,509
￥125,551 total
includes taxes & fees
Dec 15 - Dec 16
“Big Red” @ New London/Sunapee | Lake-Ski-Wellness
Exterior detail
Brook Road Condo

Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (14)
"Nice place close to the mountain!"
United States
Kevin N.
The price is ￥25,074
￥48,329 total
includes taxes & fees
Dec 23 - Dec 24
Brook Road Condo
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.
View all properties
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

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

10/10 Excellent
"Very comfortable and clean."
Christina 1-night trip
Posted 4 days ago
Courtyard by Marriott Keene Downtown

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, you can find vacation rentals near well known attractions in Windsor, or you can go with a more remote option if you're looking for relaxation.

What's the top vacation rental in Windsor?

Private Beach And Mountain Lake Home: This vacation home near Windsor is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Windsor?

Expedia has 5 vacation rentals for your stay in Windsor.

What’s there to see and do in Windsor?

Explore the area and family-friendly sights such as Eaton's Magic Morsel, or get out into nature at a spot like Black Pond. In the larger area, you’ll find Windsor Town Hall and Franklin Pierce Homestead.

What’s a vacation rental in Windsor like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Windsor. Vacation rentals provide amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for small groups.