Windsor Vacation Rentals

Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

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.
Peterborough
9.8 out of 10, Exceptional, (33 reviews)
"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
$138 nightly
The price is $149
Apr 13 - Apr 14
Total with taxes and fees
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Beach

"Seacoast" Cabin at Keyser Pond Campground

"Seacoast" Cabin at Keyser Pond Campground
Henniker
10.0 out of 10, Exceptional, (2 reviews)
"Very comfortable space - clean and cozy!"
United States
Ingrid K.
$232 nightly
The price is $252
Apr 13 - Apr 14
Total with taxes and fees
"Seacoast" Cabin at Keyser Pond Campground
Beach towels

Relaxing Hot Tub Getaway

Relaxing Hot Tub Getaway
Antrim
9.4 out of 10, Exceptional, (16 reviews)
"We wanted a place where we could eat and spend time together while still having space for everyone else to stretch out and this hit all the right buttons. Family weekend to visit our grandson, a student at nearby NEC, After a 3 hour drive up from the Cape, followed by an afternoon at the mall and restocking his dorm room, the hot tub was just what the doctor ordered!Rebecca is a wonderful host, very responsive, friendly, and helpful!"
United States
Jean C.
$246 nightly
The price is $267
Apr 20 - Apr 21
Total with taxes and fees
Relaxing Hot Tub Getaway
Fridge, microwave, oven, stovetop

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
Sunapee
10.0 out of 10, Exceptional, (57 reviews)
"Loved our stay and will definitely return!"
United States
Jenifer S.
$388 nightly
The price is $420
Apr 13 - Apr 14
Total with taxes and fees
Chic Farmhouse Decor | Deck w/View
Terrace/patio

Private Hot Tub Suite

Private Hot Tub Suite
Antrim
8.4 out of 10, Very Good, (11 reviews)
"Host was communicative and helpful with some specific questions we had. The apartment was in a cute older house, nicely updated and set up for guests. Everything was nicely labeled to be easy to find. The hot tub was great as well!"
United States
Sarah H.
$244 nightly
The price is $265
Apr 13 - Apr 14
Total with taxes and fees
Private Hot Tub Suite
Interior

Peaceful Family Friendly Private Lake Waterfront Home Close to Beach and Hiking

Peaceful Family Friendly Private Lake Waterfront Home Close to Beach and Hiking
Bennington
10.0 out of 10, Exceptional, (12 reviews)
"Stayed for a quick night ahead of skiing at Crotched. Great location near the mountain. Place was super cute, clean and comfortable for our family of four. "
United States
Jessica H.
$342 nightly
The price is $371
Apr 13 - Apr 14
Total with taxes and fees
Peaceful Family Friendly Private Lake Waterfront Home Close to Beach and Hiking
Interior

Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi

Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
Greenfield
10.0 out of 10, Exceptional, (15 reviews)
"Charming location and beautiful setting. "
United States
Cherie G.
$241 nightly
The price is $261
Apr 13 - Apr 14
Total with taxes and fees
Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
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
Newbury
10.0 out of 10, Exceptional, (19 reviews)
"Our host went above and beyond to make our experience memorable. The house was very clean and we had a nice bottle of wine and snacks waiting for us. This house is close to the mountain and right near the lake. We will rent here again "
United States
Walter B.
$416 nightly
The price is $451
Apr 13 - Apr 14
Total with taxes and fees
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Exterior detail

Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (15 reviews)
"Location was great"
United States
Andrew P.
$296 nightly
The price is $321
Apr 13 - Apr 14
Total with taxes and fees
Brook Road Condo
Fridge, microwave, oven, stovetop

Modern Downtown 12ppl Hot Tub Fire Pit Games

Modern Downtown 12ppl Hot Tub Fire Pit Games
Keene
9.2 out of 10, Wonderful, (23 reviews)
"Nice house in a nice location. "
United States
Rob B.
$273 nightly
The price is $296
Apr 13 - Apr 14
Total with taxes and fees
Modern Downtown 12ppl Hot Tub Fire Pit Games
Exterior

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Newport
9.8 out of 10, Exceptional, (22 reviews)
"The treehouse was the perfect place to unwind and relax for a few nights. Seeing the pines covered in snow out of every window was truly magical. Clean, well stocked, and everything was in good working order. "
United States
Ashley P.
$344 nightly
The price is $373
Apr 13 - Apr 14
Total with taxes and fees
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Exterior

Unique Treehouse Near Mt Sunapee

Unique Treehouse Near Mt Sunapee
Newbury
10.0 out of 10, Exceptional, (29 reviews)
"Amazing property! Would definitely stay here again "
New Zealand
Jackie M.
$401 nightly
The price is $435
Apr 13 - Apr 14
Total with taxes and fees
Unique Treehouse Near Mt Sunapee
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (21 reviews)
"Amazing place, cozy, clean and organized. I loved it and I want to come back again."
United States
Alex F.
$310 nightly
The price is $336
Apr 21 - Apr 22
Total with taxes and fees
Owl's Nest Treehouse
Exterior

Room 10 - Queen Room

Room 10 - Queen Room
Francestown
10.0 out of 10, Exceptional, (1 review)
"Easy access to skiing Crotched mountain, great breakfast and dinner! Lovely people!"
United States
j l.
$238 nightly
The price is $258
Apr 13 - Apr 14
Total with taxes and fees
Room 10 - Queen Room
TV

Brook Road Cabin

Brook Road Cabin
Goshen
9.8 out of 10, Exceptional, (17 reviews)
"Would go back!"
United States
Elizabeth C.
$292 nightly
The price is $317
Apr 13 - Apr 14
Total with taxes and fees
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
3.5 star property
Goshen
7.8 out of 10, Good, (9 reviews)
"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
$291 nightly
The price is $315
Apr 16 - Apr 17
Total with taxes and fees
Brook Road Cabin
Exterior

Waterfront Family Getaway with Sunroom & Stunning Views

Waterfront Family Getaway with Sunroom & Stunning Views
Washington
$287 nightly
The price is $312
Apr 13 - Apr 14
Total with taxes and fees
Waterfront Family Getaway with Sunroom & Stunning Views
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
Sunapee
10.0 out of 10, Exceptional, (21 reviews)
"Great home. The hosts were accessible and responded quickly to questions. Definitely will stay there again!"
United States
Ellen V.
$397 nightly
The price is $431
Apr 20 - Apr 21
Total with taxes and fees
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Interior

•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area

•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area
Sutton
10.0 out of 10, Exceptional, (19 reviews)
"Host was extremely welcoming and the place was great."
United States
Chad C.
$374 nightly
The price is $406
Apr 16 - Apr 17
Total with taxes and fees
•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area
Fridge, microwave, oven, stovetop

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

Boutique Cottage | Patio & Fire Pit | Deck w/ View
New London
10.0 out of 10, Exceptional, (104 reviews)
"Lovely home. Very clean and nicely renovated. Will stay again when back in the area!"
United States
Cheryl S.
$497 nightly
The price is $539
Apr 13 - Apr 14
Total with taxes and fees
Boutique Cottage | Patio & Fire Pit | Deck w/ View
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

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

10/10 Excellent
"Everything was great... it would have been nice if the had food available all day instead of early morning & dinner time "
Jamie 3-night trip
Posted 5 hours ago
Courtyard by Marriott Keene Downtown

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $149 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Beautiful Private Lakefront new Log Home: This vacation home rental near Windsor is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself 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.