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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Windsor vacation rentals

Terrace/patio

1. 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.
The price is ￥25,357
￥45,444 total
includes taxes & fees
Aug 4 - Aug 5
Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
Property grounds

2. 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
The price is ￥14,009
￥18,616 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Campfire Camper Retreat - Lake Nearby!
Beach towels

3. 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 ￥26,207
￥46,367 total
includes taxes & fees
Aug 30 - Aug 31
HotTub FirePit Games Huge Backyard Family Friendly
Exterior

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

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (4 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 ￥49,581
￥94,442 total
includes taxes & fees
Aug 2 - Aug 3
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
TV

5. Brook Road Cabin

Brook Road Cabin
Goshen
9.8 out of 10, Exceptional, (17 reviews)
"Would go back!"
United States
Elizabeth C.
The price is ￥26,758
￥49,526 total
includes taxes & fees
Aug 3 - Aug 4
Brook Road Cabin
Family Cabin, 2 Bedrooms, Mountain View | Living room | 40-inch Smart TV with cable channels, TV, Netflix

6. 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 ￥28,899
￥47,067 total
includes taxes & fees
Aug 3 - Aug 4
Brook Road Cabin
Property grounds

7. 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, (25 reviews)
"Beautiful house and convenient location for a family ski trip. We'lll be back in the summer! "
United States
Rebecca B.
The price is ￥29,749
￥71,046 total
includes taxes & fees
Aug 2 - Aug 3
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Terrace/patio

8. 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.
The price is ￥47,220
￥86,756 total
includes taxes & fees
Sep 1 - Sep 2
16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
Coffee/tea maker, fridge, microwave, oven

9. 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.
The price is ￥35,100
￥72,753 total
includes taxes & fees
Sep 1 - Sep 2
Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
Exterior

10. 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 ￥39,822
￥49,356 total
includes taxes & fees
Aug 2 - Aug 3
Room 10 - Queen Room
Coffee/tea maker, fridge, microwave, oven

11. 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.
The price is ￥32,110
￥58,578 total
includes taxes & fees
Aug 2 - Aug 3
Modern Downtown Escape HotTub Fire Pit Games 12ppl
TV, fireplace, books

12. @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.
The price is ￥32,267
￥78,730 total
includes taxes & fees
Sep 1 - Sep 2
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Exterior

13. 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, (31 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.
The price is ￥51,155
￥87,782 total
includes taxes & fees
Aug 31 - Sep 1
Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
Property grounds

14. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (4 reviews)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
The price is ￥18,888
￥64,556 total
includes taxes & fees
Sep 1 - Sep 2
Lakefront Family Fun Retreat
TV, fireplace, DVD player, stereo

15. "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)
"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 ￥114,587
￥239,604 total
includes taxes & fees
Aug 5 - Aug 6
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
Coffee/tea maker, fridge, microwave, oven

16. 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, (4 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 ￥30,850
￥76,339 total
includes taxes & fees
Aug 24 - Aug 25
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
TV, offices

17. "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 ￥120,096
￥270,857 total
includes taxes & fees
Aug 4 - Aug 5
"Big Sky" Retreat Atop Sunapee with Overflow Unit
Coffee/tea maker, fridge, microwave, oven

18. 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, (108 reviews)
"Lovely home. Very clean and nicely renovated. Will stay again when back in the area!"
United States
Cheryl S.
The price is ￥58,789
￥116,730 total
includes taxes & fees
Aug 2 - Aug 3
King Hill Cottage by Sunapee Stays - Fireplace, Kids Nook, Mount Sunapee
Coffee/tea maker, fridge, microwave, oven

19. 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, (15 reviews)
"It was a nice place. "
United States
Carson C.
The price is ￥102,310
￥185,296 total
includes taxes & fees
Sep 1 - Sep 2
Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee
TV, fireplace, DVD player, stereo

20. “Big Red” @ New London/Sunapee | Lake-Ski-Wellness

“Big Red” @ New London/Sunapee | Lake-Ski-Wellness
New London
10.0 out of 10, Exceptional, (15 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 ￥89,088
￥256,681 total
includes taxes & fees
Aug 5 - Aug 6
“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

The New London Inn

The New London Inn

8/10 Good
"A very nice historic building that has been kept very stately. The front porch sitting area was relaxing. The restaurant had wonderful food and nice ambiance. Location in town is convenient. A very peaceful stay as inn was not crowded."
Anthony 3-night trip
Posted 2 days ago
The New London Inn

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 Custom 5 Bed Home Minutes to Mt.Sunapee! Garage, Hot Tub, Game Room!: This vacation home near Windsor is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 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 selection of games and a hot tub.

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.