Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

Cozy & Bright Guest Suite

Cozy & Bright Guest Suite
Peterborough
$175 nightly
The price is $190
Mar 1 - Mar 2
Total with taxes and fees
Cozy & Bright Guest Suite

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, (31 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
$151 nightly
The price is $164
Mar 2 - Mar 3
Total with taxes and fees
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

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 1 - Mar 2
Total with taxes and fees
Relaxing Hot Tub Getaway

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.
$418 nightly
The price is $454
Mar 2 - Mar 3
Total with taxes and fees
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Quiet Cabin rental near Pat's Peak - Seacoast

Quiet Cabin rental near Pat's Peak - Seacoast
Henniker
10.0 out of 10, Exceptional, (1 review)
"Adorable place! Excellent job removing snow during a storm. We will definitely return!"
United States
Meg V.
$198 nightly
The price is $214
Mar 1 - Mar 2
Total with taxes and fees
Quiet Cabin rental near Pat's Peak - Seacoast

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
Sunapee
10.0 out of 10, Exceptional, (55 reviews)
"Loved our stay and will definitely return!"
United States
Jenifer S.
$396 nightly
The price is $430
Mar 2 - Mar 3
Total with taxes and fees
Chic Farmhouse Decor | Deck w/View

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.
$232 nightly
The price is $252
Mar 5 - Mar 6
Total with taxes and fees
Private Hot Tub Suite

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
$296 nightly
The price is $321
Mar 15 - Mar 16
Total with taxes and fees
Brook Road Cabin

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, (10 reviews)
"Good 2-bedroom cabin close to Crotched skiing/boarding. Scenic frozen lake views. Cozy beds. Nice!"
United States
Matthew
$313 nightly
The price is $339
Mar 2 - Mar 3
Total with taxes and fees
Peaceful Family Friendly Private Lake Waterfront Home 8 Min to Skiing & Hiking

Book your ski vacations for the upcoming season.

Book your ski vacations for the upcoming season.
Sutton
10.0 out of 10, Exceptional, (17 reviews)
"Perfect house for our stay!"
United States
Shelley R.
$352 nightly
The price is $381
Feb 27 - Feb 28
Total with taxes and fees
Book your ski vacations for the upcoming season.

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.
$266 nightly
The price is $289
Mar 3 - Mar 4
Total with taxes and fees
Modern Downtown 12ppl Hot Tub Fire Pit Games

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, (12 reviews)
"Its was great clean, quite and comfortable. "
United States
John G.
$222 nightly
The price is $240
Feb 27 - Feb 28
Total with taxes and fees
Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi

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.
$408 nightly
The price is $443
Mar 1 - Mar 2
Total with taxes and fees
Unique Treehouse Near Mt Sunapee

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.
$181 nightly
The price is $196
Mar 16 - Mar 17
Total with taxes and fees
Room 10 - Queen Room

Large 3BR Apartment in Marlborough NH: Sleeps 8-10: Close to Keene!

Large 3BR Apartment in Marlborough NH: Sleeps 8-10: Close to Keene!
Marlborough
10.0 out of 10, Exceptional, (2 reviews)
"Clean and close to Keene! Very quiet and had a great nights rest!"
United States
Sierra M.
$293 nightly
The price is $317
Feb 27 - Feb 28
Total with taxes and fees
Large 3BR Apartment in Marlborough NH: Sleeps 8-10: Close to Keene!

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (19 reviews)
"10/10 across the board! The cabin was a great experience. The hot tub was amazing. They have their own store near by with lots of goodies. They were very helpful with any questions we had. Would come here again!"
United States
Adriana
$310 nightly
The price is $336
Mar 1 - Mar 2
Total with taxes and fees
Owl's Nest Treehouse

Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (14 reviews)
"Nice place close to the mountain!"
United States
Kevin N.
$291 nightly
The price is $316
Mar 8 - Mar 9
Total with taxes and fees
Brook Road Condo

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
$276 nightly
The price is $299
Mar 8 - Mar 9
Total with taxes and fees
Brook Road Condo

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.
$559 nightly
The price is $607
Mar 2 - Mar 3
Total with taxes and fees
Boutique Cottage | Patio & Fire Pit | Deck w/ View

Central Large 2-bedrooms with office in Keene

Central Large 2-bedrooms with office in Keene
Keene
10.0 out of 10, Exceptional, (1 review)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
$158 nightly
The price is $171
Mar 3 - Mar 4
Total with taxes and fees
Central Large 2-bedrooms with office in Keene
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

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 $164 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.

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?

"Big Sky" Retreat Atop Sunapee with Overflow Unit: Located near Windsor, this vacation home rental offers a hot tub, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings.

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.