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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Windsor vacation rentals

Property grounds

Cozy Campfire Camper Retreat - Lake Nearby!

Cozy Campfire Camper Retreat - Lake Nearby!
Henniker
10.0 out of 10, Exceptional, (1 review)
"Excellent visit! Comfortable and the host was extremely helpful!"
United States
Nicholas
$100 nightly
The price is $109
Jul 14 - Jul 15
Total with taxes and fees
Cozy Campfire Camper Retreat - Lake Nearby!
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, (39 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
$151 nightly
The price is $164
Jul 14 - Jul 15
Total with taxes and fees
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Fridge, microwave, oven, stovetop

Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee

Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
Sunapee
10.0 out of 10, Exceptional, (58 reviews)
"Wonderful place to stay for our trip. Great location and the house was nicely updated. "
United States
Andrew W.
$434 nightly
The price is $471
Jul 16 - Jul 17
Total with taxes and fees
Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
Beach towels

HotTub FirePit Games Huge Backyard Family Friendly

HotTub FirePit Games Huge Backyard Family Friendly
Antrim
9.4 out of 10, Exceptional, (16 reviews)
"The hot tub was great and the peace and quiet was very nice."
United States
Brian B.
$253 nightly
The price is $274
Jul 22 - Jul 23
Total with taxes and fees
HotTub FirePit Games Huge Backyard Family Friendly
Interior

•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area

•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area
Sutton
10.0 out of 10, Exceptional, (20 reviews)
"Host was extremely welcoming and the place was great."
United States
Chad C.
$377 nightly
The price is $409
Jul 15 - Jul 16
Total with taxes and fees
•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area
Terrace/patio

Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl

Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
Antrim
9.6 out of 10, Exceptional, (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.
$246 nightly
The price is $267
Jul 14 - Jul 15
Total with taxes and fees
Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
Fridge, microwave, oven, stovetop

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (25 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
$290 nightly
The price is $315
Jul 15 - Jul 16
Total with taxes and fees
Modern Downtown Escape HotTub Fire Pit Games 12ppl
TV

Brook Road Cabin

Brook Road Cabin
Goshen
9.8 out of 10, Exceptional, (17 reviews)
"Would go back!"
United States
Elizabeth C.
$298 nightly
The price is $323
Jul 14 - Jul 15
Total with taxes and fees
Brook Road Cabin
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, (23 reviews)
"Beautiful house and convenient location for a family ski trip. We'lll be back in the summer! "
United States
Rebecca B.
$477 nightly
The price is $518
Jul 15 - Jul 16
Total with taxes and fees
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Exterior

Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee

Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
Newbury
10.0 out of 10, Exceptional, (30 reviews)
"Such a magical, detail-oriented design--it was so fun just exploring all the creative elements built into the treehouse, and everything was luxurious and comfy. We had a lovely stay!"
United States
GennaRose N.
$415 nightly
The price is $450
Jul 15 - Jul 16
Total with taxes and fees
Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
Fridge, microwave, oven, stovetop

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (3 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
$442 nightly
The price is $480
Jul 14 - Jul 15
Total with taxes and fees
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
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
7.4 out of 10, Good, (10 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
$282 nightly
The price is $306
Jul 14 - Jul 15
Total with taxes and fees
Brook Road Cabin
Terrace/patio

16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard

16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
Antrim
9.8 out of 10, Exceptional, (10 reviews)
"This was a great property. We had a wonderful stay here for a large group. Rebecca is a great host- so responsive and helpful before and during our stay. Highly recommend! "
United States
Kyra D.
$571 nightly
The price is $619
Jul 22 - Jul 23
Total with taxes and fees
16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
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.
$289 nightly
The price is $314
Jul 15 - Jul 16
Total with taxes and fees
Room 10 - Queen Room
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, (26 reviews)
"The perfect winter stay for our family! Perfect location, close to Mount Sunapee. Gorgeous views and home. Host was extremely welcoming and responsive, and the whole stay was easy."
United States
Amanda R.
$610 nightly
The price is $662
Aug 2 - Aug 3
Total with taxes and fees
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
TV, fireplace, DVD player, stereo

"Big Sky" Retreat Atop Sunapee / Ski + Lake Life

"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
Newbury
10.0 out of 10, Exceptional, (11 reviews)
"We had an amazing stay! The property was beautiful and the hosts were awesome. It was the perfect place to host a big group. We particularly enjoyed the big kitchen for cooking large meals and the outdoor deck seating. This place was great and we would happily stay again!"
United States
Lilly N.
$1,164 nightly
The price is $1,263
Jul 14 - Jul 15
Total with taxes and fees
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
Fridge, microwave, oven, stovetop

Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
Dublin
10.0 out of 10, Exceptional, (26 reviews)
"Good place to stay during a wedding week"
United States
Veronique S.
$686 nightly
The price is $729
Jul 14 - Jul 15
Total with taxes and fees
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
Fridge, microwave, oven, stovetop

King Hill Cottage by Sunapee Stays - Fireplace, Kids Nook, Mount Sunapee

King Hill Cottage by Sunapee Stays - Fireplace, Kids Nook, Mount Sunapee
New London
10.0 out of 10, Exceptional, (105 reviews)
"Lovely home. Very clean and nicely renovated. Will stay again when back in the area!"
United States
Cheryl S.
$686 nightly
The price is $744
Jul 16 - Jul 17
Total with taxes and fees
King Hill Cottage by Sunapee Stays - Fireplace, Kids Nook, Mount Sunapee
Exterior

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

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (3 reviews)
"Everything was perfect for our weekend stay. Host responded immediately to our questions. House had all the amenities for an enjoyable time!"
United States
Mary P.
$582 nightly
The price is $631
Jul 15 - Jul 16
Total with taxes and fees
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Smart TV, video games, books

Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee

Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee
Sunapee
9.6 out of 10, Exceptional, (8 reviews)
"Great stay, the boys will be back! "
United States
Susan B.
$743 nightly
The price is $806
Jul 20 - Jul 21
Total with taxes and fees
Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to 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.
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Top Windsor Hotel Reviews

The Burrell House

The Burrell House

10/10 Excellent
"Wonderful stay"
Justin 1-night trip
Posted 2 hours ago
The Burrell House

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?

HISTORIC, RENOVATED BARN w/ Mt. SUNAPEE VIEW, SLEEPS 22+, Minutes to Lake / Mt.: This vacation home 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 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 Quilted Threads, 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.