Windsor Vacation Rentals

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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Windsor vacation rentals

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
The price is ￥29,323
￥47,758 total
includes taxes & fees
Apr 26 - Apr 27
Brook Road Cabin
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.
The price is ￥29,504
￥42,049 total
includes taxes & fees
Apr 28 - Apr 29
Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
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.
The price is ￥28,604
￥64,306 total
includes taxes & fees
Apr 26 - Apr 27
Chic Farmhouse Decor | Deck w/View
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.
The price is ￥28,706
￥65,235 total
includes taxes & fees
Apr 25 - Apr 26
•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area
Beach

"Seacoast" Cabin at Keyser Pond Campground

"Seacoast" Cabin at Keyser Pond Campground
Henniker
10.0 out of 10, Exceptional, (3 reviews)
"Very comfortable space - clean and cozy!"
United States
Ingrid K.
The price is ￥24,719
￥40,146 total
includes taxes & fees
Apr 30 - May 1
"Seacoast" Cabin at Keyser Pond Campground
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (21 reviews)
"Great time easy to get to clean quiet and peaceful definitely would recommend for romantic getaway "
United States
Garrett B.
The price is ￥43,857
￥54,161 total
includes taxes & fees
Apr 29 - Apr 30
Owl's Nest Treehouse
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, (34 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
The price is ￥15,811
￥29,286 total
includes taxes & fees
Apr 26 - Apr 27
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
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)
"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.
The price is ￥22,855
￥42,993 total
includes taxes & fees
May 5 - May 6
HotTub FirePit Games Huge Backyard Family Friendly
Terrace/patio

Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl

Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
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.
The price is ￥22,822
￥42,585 total
includes taxes & fees
Apr 26 - Apr 27
Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
Exterior

Luxury Treehouse Near Mount Sunapee | Fireplace + Deck

Luxury Treehouse Near Mount Sunapee | Fireplace + Deck
Newbury
10.0 out of 10, Exceptional, (30 reviews)
"Outstanding host and property—clean, beautiful, and really unique. Can’t wait to return!"
United States
Austin G.
The price is ￥37,372
￥70,181 total
includes taxes & fees
Apr 26 - Apr 27
Luxury Treehouse Near Mount Sunapee | Fireplace + Deck
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
The price is ￥29,344
￥47,757 total
includes taxes & fees
May 7 - May 8
Brook Road Condo
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.
The price is ￥30,142
￥71,985 total
includes taxes & fees
May 7 - May 8
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
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)
"The house was super clean, great distance to the mountain for skiing and restaurants, and the host was extremely helpful and accommodating!"
United States
Stephen S.
The price is ￥29,209
￥59,206 total
includes taxes & fees
Apr 26 - Apr 27
Peaceful Family Friendly Private Lake Waterfront Home Close to Beach and Hiking
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.
The price is ￥35,883
￥87,904 total
includes taxes & fees
Apr 26 - Apr 27
Boutique Cottage | Patio & Fire Pit | Deck w/ View
Exterior detail

Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (15 reviews)
"Location was great"
United States
Andrew P.
The price is ￥27,112
￥50,701 total
includes taxes & fees
Apr 30 - May 1
Brook Road Condo
Fridge, microwave, oven, stovetop

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.2 out of 10, Wonderful, (23 reviews)
"Nice house in a nice location. "
United States
Rob B.
The price is ￥23,078
￥47,913 total
includes taxes & fees
Apr 26 - Apr 27
Modern Downtown Escape HotTub Fire Pit Games 12ppl
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.
The price is ￥33,156
￥41,165 total
includes taxes & fees
Apr 26 - Apr 27
Room 10 - Queen Room
Fridge, microwave, oven, stovetop

Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee

Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee
Newbury
10.0 out of 10, Exceptional, (13 reviews)
"It was a nice place. "
United States
Carson C.
The price is ￥86,243
￥161,329 total
includes taxes & fees
Apr 25 - Apr 26
Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee
TV, fireplace, DVD player, books

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

"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
Newbury
10.0 out of 10, Exceptional, (10 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.
The price is ￥60,370
￥173,806 total
includes taxes & fees
Apr 27 - Apr 28
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
TV, fireplace, DVD player, books

“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 reviews)
"Fantastic property and host! An excellent home base for skiing at Mt. Sunapee. Especially loved the hot tub and fire pit."
United States
Kurt W.
The price is ￥55,419
￥216,780 total
includes taxes & fees
Apr 27 - Apr 28
“Big Red” @ New London/Sunapee | Lake-Ski-Wellness
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

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

10/10 Excellent
"Best place around for a nice family get away and small gathering"
Jadecyn 1-night trip
Posted 4 hours ago
Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

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?

Spacious 3BR Home Near Lake & Mountain - Sleeps 9 - Sunapee Retreat: This vacation home rental near Windsor is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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.