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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 homes

A hot tub with a view of an outdoor area with trees and a wooden structure.

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

4. 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 modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

5. 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 hot tub in a rustic interior with wooden beams, a staircase, and seating areas.

6. 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 conservatory with a view of a lake surrounded by trees. Inside, there are two sofas facing the glass walls.

7. 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 wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

8. 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 cozy living room with a sofa, a dining table with chairs, a small side table, and a wooden floor.

9. 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 yellow building with a porch and a sign that reads "Brook Road Inn."

10. Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (15 reviews)
"Nice place for a mountain stay"
United States
Meghan B.
The price is CA $238
CA $433 total
includes taxes & fees
Nov 9 - Nov 10
Brook Road Condo
A wooden cabin with multiple windows and a balcony, surrounded by trees.

11. 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 $408
CA $711 total
includes taxes & fees
Nov 10 - Nov 11
Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a hanging light fixture.

12. 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 spacious living room with a large sectional sofa, a glass coffee table, and a high ceiling with exposed wooden beams.

13. "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 spacious living room with a high ceiling, exposed wooden beams, and a large window providing natural light.

14. "Big Sky" Retreat Atop Sunapee with Overflow Unit

"Big Sky" Retreat Atop Sunapee with Overflow Unit
Newbury
10.0 out of 10, Exceptional, (1 review)
The price is CA $663
CA $1,810 total
includes taxes & fees
Nov 9 - Nov 10
"Big Sky" Retreat Atop Sunapee with Overflow Unit
A spacious living room with a fireplace, large windows, and a cozy seating area.

15. @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 large wooden house with multiple levels, a balcony, and a staircase leading to the entrance.

16. Spectacular Fall Color! 20 Min to Ragged Mtn and Mt. Sunapee | Sleeps 6

Spectacular Fall Color! 20 Min to Ragged Mtn and Mt. Sunapee | Sleeps 6
North Sutton
The price is CA $377
CA $914 total
includes taxes & fees
Nov 15 - Nov 16
Spectacular Fall Color! 20 Min to Ragged Mtn and Mt. Sunapee | Sleeps 6
A kitchen with a wooden countertop, four white bar stools, a black refrigerator, and a window with a view of trees.

17. 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, (21 reviews)
"Nice and clean"
United States
Ludwin
The price is CA $883
CA $1,536 total
includes taxes & fees
Nov 9 - Nov 10
Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

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

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
9.8 out of 10, Exceptional, (6 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.
The price is CA $269
CA $642 total
includes taxes & fees
Nov 9 - Nov 10
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

19. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (27 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is CA $289
CA $502 total
includes taxes & fees
Nov 9 - Nov 10
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A modern kitchen with a central island, bar stools, and a fireplace.

20. 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, (109 reviews)
"A fabulous cottage in a great location. Practically perfect in every way! Great Hosts!!"
United States
John M.
The price is CA $360
CA $862 total
includes taxes & fees
Nov 9 - Nov 10
King Hill Cottage by Sunapee Stays - Fireplace, Kids Nook, Mount 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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good
"Overall a nice stay. What was disappointing was breakfast ends at 9am. Very disappointed when we came down to eat at 9:15 and it was roped off and over."
Michael 1-night trip
Posted 11 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews
384
Accommodation
127 Vacation Homes
Lowest Price
CA $412
Highest Price
CA $1,810

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