Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Windsor vacation rentals

A house with a deck and a dock extending into a pond, surrounded by autumn foliage.

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

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (6 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.
The price is CA $473
CA $846 total
includes taxes & fees
Nov 9 - Nov 10
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
A hot tub with a wooden deck and a hammock in a backyard.

2. 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.
The price is CA $251
CA $420 total
includes taxes & fees
Nov 9 - Nov 10
HotTub FirePit Games Huge Backyard Family Friendly
A hot tub in a rustic interior with wooden beams, a staircase, and seating areas.

3. Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl

Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
Antrim
9.0 out of 10, Wonderful, (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 CA $251
CA $420 total
includes taxes & fees
Nov 11 - Nov 12
Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
A hot tub in a rustic interior with wooden beams, a staircase, and seating areas.

4. 16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard

16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
Antrim
10.0 out of 10, Exceptional, (11 reviews)
"Great place to relax with a woody vibe. Excellent stay"
United States
Logan V.
The price is CA $566
CA $913 total
includes taxes & fees
Nov 11 - Nov 12
16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
A wooden cabin with multiple windows and a balcony, surrounded by trees.

5. 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, (32 reviews)
"Great experience and an amazing property"
United States
Tim D.
The price is CA $392
CA $712 total
includes taxes & fees
Nov 8 - Nov 9
Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

6. SUNAPEE RETREAT AT ENCHANTED FOREST - BRING KIDS - NEAR LAKE AND MOUNTAIN!

SUNAPEE RETREAT AT ENCHANTED FOREST - BRING KIDS - NEAR LAKE AND MOUNTAIN!
Newbury
9.8 out of 10, Exceptional, (21 reviews)
"Neat place, close to two ski mountains. "
United States
COLLEEN K.
The price is CA $223
CA $1,501 total
includes taxes & fees
Nov 17 - Nov 18
SUNAPEE RETREAT AT ENCHANTED FOREST - BRING KIDS - NEAR LAKE AND MOUNTAIN!
A modern living room with a sectional sofa, a wooden coffee table, and a large window with blinds.

7. 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
The price is CA $252
CA $414 total
includes taxes & fees
Dec 8 - Dec 9
Brook Road Cabin
A hot tub with a view of an outdoor area with trees and a wooden structure.

8. Family Friendly, Hot Tub, King Beds Just Renovated

Family Friendly, Hot Tub, King Beds Just Renovated
Hillsborough
The price is CA $289
CA $458 total
includes taxes & fees
Nov 9 - Nov 10
Family Friendly, Hot Tub, King Beds Just Renovated
A conservatory with a view of a lake surrounded by trees. Inside, there are two sofas facing the glass walls.

9. Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking

Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking
Bennington
10.0 out of 10, Exceptional, (16 reviews)
"Very cozy house Perfect for all family trip Very clean "
United States
Marcin W.
The price is CA $270
CA $526 total
includes taxes & fees
Nov 18 - Nov 19
Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a hanging light fixture.

10. 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, (59 reviews)
"Wonderful place to stay for our trip. Great location and the house was nicely updated. "
United States
Andrew W.
The price is CA $297
CA $643 total
includes taxes & fees
Nov 9 - Nov 10
Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
A cozy living room with a large sectional sofa, a wooden coffee table, and a view of trees through a window.

11. Brook Road Cabin

Brook Road Cabin
Goshen
9.6 out of 10, Exceptional, (18 reviews)
"Would go back!"
United States
Elizabeth C.
The price is CA $238
CA $433 total
includes taxes & fees
Nov 9 - Nov 10
Brook Road Cabin
A forested area with a gravel path leading to a cabin with a metal roof and a wooden deck.

12. 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, (28 reviews)
"Great time at the hideaway!"
United States
Melissa O.
The price is CA $265
CA $659 total
includes taxes & fees
Nov 9 - Nov 10
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
A spacious living room with a fireplace, large windows, and a cozy seating area.

13. @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, (28 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.
The price is CA $261
CA $823 total
includes taxes & fees
Dec 6 - Dec 7
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
A house entrance with a mailbox labeled '9B Mail', a wooden door, and a brick wall interior visible through the open door.

14. 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, (48 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is CA $115
CA $219 total
includes taxes & fees
Nov 9 - Nov 10
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
A modern living room with a wooden door, a sofa, a dining table with chairs, and a mounted TV.

15. Cozy Tiny House on Main Street. Fully Renovated.

Cozy Tiny House on Main Street. Fully Renovated.
Dublin
10.0 out of 10, Exceptional, (5 reviews)
"This was a perfect place to stay for my solo trip into town for a family wedding. The host was incredibly responsive and friendly and I'd recommend this place to anyone visiting the area!"
United States
David W.
The price is CA $294
CA $420 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Tiny House on Main Street. Fully Renovated.
A cluster of white buildings with multiple chimneys, surrounded by lush green grass and trees with autumn foliage.

16. 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 CA $327
CA $368 total
includes taxes & fees
Nov 9 - Nov 10
Room 10 - Queen Room
A cozy living room with a sofa, a dining table with chairs, a small side table, and a wooden floor.

17. 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 CA $250
CA $412 total
includes taxes & fees
Dec 8 - Dec 9
Brook Road Condo
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

18. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 reviews)
"Had a lot here to use and The place was very cute. It’s good if you have small kids they have a lot for that sort of thing. Very clean as well"
United States
sean c.
The price is CA $182
CA $554 total
includes taxes & fees
Nov 10 - Nov 11
Lakefront Family Fun Retreat
A spacious living room with a large sectional sofa, a glass coffee table, and a high ceiling with exposed wooden beams.

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

"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
Newbury
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful house in a nice location. Close to the lake, ski area and hiking. It was the perfect space to have a mini reunion with some friends."
United States
William B.
The price is CA $540
CA $1,462 total
includes taxes & fees
Nov 9 - Nov 10
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
A red house with a stone pathway leading to it, surrounded by autumn foliage.

20. Cobb Meadow House: Cozy 5 Bedroom Retreat

Cobb Meadow House: Cozy 5 Bedroom Retreat
Dublin
10.0 out of 10, Exceptional, (27 reviews)
"Good place to stay during a wedding week"
United States
Veronique S.
The price is CA $589
CA $943 total
includes taxes & fees
Nov 9 - Nov 10
Cobb Meadow House: Cozy 5 Bedroom Retreat
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

A stone-clad building entrance with a covered patio and benches.
Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel
Newbury

10/10 Excellent

Very beautiful and welcoming. Spacious rooms with everything one can need! Fireplace was a nice bonus!
Canada
Silvana
Reviewed November 16, 2024
Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor vacation rentals we have selected for you start as low as CA $114 per night. Entering your travel dates in the search wizard 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 Friendly Farm, 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.