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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 ￥53,443
￥94,924 total
includes taxes & fees
Nov 8 - Nov 9
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 ￥28,360
￥47,093 total
includes taxes & fees
Nov 8 - Nov 9
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
8.8 out of 10, Excellent, (12 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 ￥28,386
￥47,308 total
includes taxes & fees
Nov 12 - Nov 13
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 ￥63,989
￥102,932 total
includes taxes & fees
Nov 12 - Nov 13
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 ￥43,933
￥80,856 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 ￥25,178
￥161,674 total
includes taxes & fees
Nov 19 - Nov 20
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 ￥29,073
￥47,350 total
includes taxes & fees
Nov 8 - Nov 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 ￥32,636
￥51,388 total
includes taxes & fees
Nov 16 - Nov 17
Family Friendly, Hot Tub, King Beds Just Renovated
A room with a wooden dresser, a mirror, and a wardrobe with shelves.

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 ￥29,587
￥57,724 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 ￥33,549
￥73,717 total
includes taxes & fees
Nov 8 - Nov 9
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 ￥26,920
￥48,451 total
includes taxes & fees
Nov 17 - Nov 18
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 ￥29,928
￥70,958 total
includes taxes & fees
Nov 10 - Nov 11
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, (27 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 ￥27,078
￥88,999 total
includes taxes & fees
Nov 11 - Nov 12
@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 ￥13,681
￥25,495 total
includes taxes & fees
Nov 10 - Nov 11
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 ￥33,254
￥47,434 total
includes taxes & fees
Nov 7 - Nov 8
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 ￥36,927
￥43,502 total
includes taxes & fees
Nov 15 - Nov 16
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 ￥25,643
￥43,642 total
includes taxes & fees
Nov 10 - Nov 11
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 ￥20,513
￥64,007 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 ￥61,019
￥165,256 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 ￥66,566
￥108,663 total
includes taxes & fees
Nov 8 - Nov 9
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

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

10/10 Excellent
"Nice choice of ordering food you can either eat in the dining area or take back to your room."
Sharon 2-night trip
Posted 2 days ago
Courtyard by Marriott Keene Downtown

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?

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.