Windsor Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 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.
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
$147 nightly
The price is $159
Mar 15 - Mar 16
Total with taxes and fees
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Exterior

Cozy & Bright Guest Suite

Cozy & Bright Guest Suite
Peterborough
$193 nightly
The price is $210
Mar 11 - Mar 12
Total with taxes and fees
Cozy & Bright Guest Suite
Exterior

"Seacoast" cabin at Keyser Pond Campground

"Seacoast" cabin at Keyser Pond Campground
Henniker
10.0 out of 10, Exceptional, (2 reviews)
"Adorable place! Excellent job removing snow during a storm. We will definitely return!"
United States
Meg V.
$215 nightly
The price is $233
Mar 11 - Mar 12
Total with taxes and fees
"Seacoast" cabin at Keyser Pond Campground
Smart TV, fireplace, video games, table tennis

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.
$236 nightly
The price is $256
Mar 11 - Mar 12
Total with taxes and fees
Relaxing Hot Tub Getaway
Terrace/patio

Private Hot Tub Suite

Private Hot Tub Suite
Antrim
9.0 out of 10, Wonderful, (10 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.
$236 nightly
The price is $256
Mar 12 - Mar 13
Total with taxes and fees
Private Hot Tub Suite
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, (21 reviews)
"The tree house was just as pictured, beautiful inside and we had great views of the River. It was a great trip and we look forward to coming back!"
United States
Kimberly R.
$345 nightly
The price is $374
Mar 15 - Mar 16
Total with taxes and fees
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Interior

Peaceful Family Friendly Private Lake Waterfront Home 8 Min to Skiing & Hiking

Peaceful Family Friendly Private Lake Waterfront Home 8 Min to Skiing & Hiking
Bennington
10.0 out of 10, Exceptional, (11 reviews)
"Good 2-bedroom cabin close to Crotched skiing/boarding. Scenic frozen lake views. Cozy beds. Nice!"
United States
Matthew
$342 nightly
The price is $371
Mar 15 - Mar 16
Total with taxes and fees
Peaceful Family Friendly Private Lake Waterfront Home 8 Min to Skiing & Hiking
Exterior detail

Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (14 reviews)
"Location was great"
United States
Andrew P.
$296 nightly
The price is $321
Mar 15 - Mar 16
Total with taxes and fees
Brook Road Condo
Outdoor spa tub

Modern Downtown 12ppl Hot Tub Fire Pit Games

Modern Downtown 12ppl Hot Tub Fire Pit Games
Keene
9.6 out of 10, Exceptional, (22 reviews)
"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.
$271 nightly
The price is $294
Apr 6 - Apr 7
Total with taxes and fees
Modern Downtown 12ppl Hot Tub Fire Pit Games
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, (18 reviews)
"We loved our weekend experience at the Hideaway! "
United States
Benjamin M.
$416 nightly
The price is $451
Mar 11 - Mar 12
Total with taxes and fees
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Fridge, microwave, oven, stovetop

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
Sunapee
10.0 out of 10, Exceptional, (56 reviews)
"Loved our stay and will definitely return!"
United States
Jenifer S.
$412 nightly
The price is $447
Mar 15 - Mar 16
Total with taxes and fees
Chic Farmhouse Decor | Deck w/View
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (19 reviews)
"We loved our stay at The Owls Nest! The location was very private, and everything was exceptionally clean. Perfect for a quick weekend getaway to relax. Would highly recommend for a couple looking to enjoy a quiet weekend. "
United States
Samantha R.
$310 nightly
The price is $336
Mar 11 - Mar 12
Total with taxes and fees
Owl's Nest Treehouse
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, (13 reviews)
"Charming location and beautiful setting. "
United States
Cherie G.
$217 nightly
The price is $235
Mar 15 - Mar 16
Total with taxes and fees
Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
Exterior

Unique Treehouse Near Mt Sunapee

Unique Treehouse Near Mt Sunapee
Newbury
10.0 out of 10, Exceptional, (28 reviews)
"Great stay. Had a wonderful time."
United States
Chris P.
$421 nightly
The price is $456
Mar 11 - Mar 12
Total with taxes and fees
Unique Treehouse Near Mt Sunapee
TV

Brook Road Cabin

Brook Road Cabin
Goshen
9.8 out of 10, Exceptional, (17 reviews)
"Would go back!"
United States
Elizabeth C.
$299 nightly
The price is $324
Mar 15 - Mar 16
Total with taxes and fees
Brook Road Cabin
Interior

Spring Ski vacation bookings are here and NH Maple Weekend!

Spring Ski vacation bookings are here and NH Maple Weekend!
Sutton
10.0 out of 10, Exceptional, (19 reviews)
"Perfect house for our stay!"
United States
Shelley R.
$352 nightly
The price is $381
Mar 12 - Mar 13
Total with taxes and fees
Spring Ski vacation bookings are here and NH Maple Weekend!
Exterior

Ski Minutes Away & Pool Onsite

Ski Minutes Away & Pool Onsite
Henniker
10.0 out of 10, Exceptional, (9 reviews)
"A lovely place to stay while visiting the area for the weekend. Key pad check in was seamless, and communication with the host was top notch. Would recommend and stay here again!"
United States
Sarah A.
$461 nightly
The price is $500
Mar 11 - Mar 12
Total with taxes and fees
Ski Minutes Away & Pool Onsite
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.
$140 nightly
The price is $152
Mar 16 - Mar 17
Total with taxes and fees
Room 10 - Queen Room
Comfort Townhome | In-room dining

Brook Road Condo

Brook Road Condo
3.0 star property
Goshen
8.8 out of 10, Excellent, (3 reviews)
"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."
United States
Margaret
$264 nightly
The price is $286
Mar 16 - Mar 17
Total with taxes and fees
Brook Road Condo
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, (20 reviews)
"Great home. The hosts were accessible and responded quickly to questions. Definitely will stay there again!"
United States
Ellen V.
$406 nightly
The price is $441
Mar 30 - Mar 31
Total with taxes and fees
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
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

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
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

Newport Motel

Newport Motel

10/10 Excellent
"Yes."
Brian 1-night trip
Posted 1 day ago
Newport Motel

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 $159 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?

HISTORIC, RENOVATED BARN w/ Mt. SUNAPEE VIEW, SLEEPS 22+, Minutes to Lake / Mt.: Located near Windsor, this vacation home rental 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 7 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 library.

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.