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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Windsor vacation rentals

Beach towels

1. 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 AED 612
AED 1,102 total
includes taxes & fees
19 Aug - 20 Aug
HotTub FirePit Games Huge Backyard Family Friendly
Terrace/patio

2. 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 AED 657
AED 1,160 total
includes taxes & fees
31 Aug - 1 Sep
Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
Exterior

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

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (5 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 AED 1,377
AED 2,507 total
includes taxes & fees
20 Aug - 21 Aug
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Terrace/patio

4. 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 AED 1,120
AED 2,072 total
includes taxes & fees
1 Sep - 2 Sep
16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
Family Cabin, 2 Bedrooms, Mountain View | Living room | 40-inch Smart TV with cable channels, TV, Netflix

5. 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 AED 674
AED 1,098 total
includes taxes & fees
16 Aug - 17 Aug
Brook Road Cabin
TV

6. 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 AED 624
AED 1,196 total
includes taxes & fees
26 Aug - 27 Aug
Brook Road Cabin
Interior

7. 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, (14 reviews)
"Very cozy house Perfect for all family trip Very clean "
United States
Marcin W.
The price is AED 724
AED 1,447 total
includes taxes & fees
2 Sep - 3 Sep
Peaceful Family Friendly Private Lake Waterfront Home Close to Beach and Hiking
Interior

8. •   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area

•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area
Sutton
10.0 out of 10, Exceptional, (21 reviews)
"Host was extremely welcoming and the place was great."
United States
Chad C.
The price is AED 698
AED 1,522 total
includes taxes & fees
12 Sep - 13 Sep
•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area
Exterior detail

9. 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
10.0 out of 10, Exceptional, (41 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is AED 380
AED 699 total
includes taxes & fees
26 Aug - 27 Aug
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Coffee/tea maker, fridge, microwave, oven

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, (58 reviews)
"Wonderful place to stay for our trip. Great location and the house was nicely updated. "
United States
Andrew W.
The price is AED 771
AED 1,642 total
includes taxes & fees
7 Sep - 8 Sep
Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
Property grounds

11. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 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.
Lakefront Family Fun Retreat
Exterior

12. 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 AED 929
AED 1,148 total
includes taxes & fees
13 Sep - 14 Sep
Room 10 - Queen Room
Property grounds

13. 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)
"It was excellent… missing tissues and address was confusing.. but would stay again in a heartbeat!! "
United States
Nancy L.
The price is AED 771
AED 1,777 total
includes taxes & fees
8 Sep - 9 Sep
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Exterior

14. 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 AED 1,117
AED 1,941 total
includes taxes & fees
14 Sep - 15 Sep
Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
Coffee/tea maker, fridge, microwave, oven

15. 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 AED 749
AED 1,379 total
includes taxes & fees
17 Aug - 18 Aug
Modern Downtown Escape HotTub Fire Pit Games 12ppl
TV, fireplace, DVD player, stereo

16. "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.
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
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)
"Big Sky" Retreat Atop Sunapee with Overflow Unit
TV, fireplace, books

18. @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 AED 918
AED 2,032 total
includes taxes & fees
31 Aug - 1 Sep
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Coffee/tea maker, fridge, microwave, oven

19. 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.
King Hill Cottage by Sunapee Stays - Fireplace, Kids Nook, Mount Sunapee
Coffee/tea maker, fridge, microwave, oven

20. 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 AED 2,149
AED 3,981 total
includes taxes & fees
13 Sep - 14 Sep
Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake 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

Colby Hill Inn

Colby Hill Inn

8/10 Good
"Loved the inn well maintained comfortable beds clean rooms. The breakfast was excellent"
Tom 1-night trip
Posted 20 hours ago
Colby Hill Inn

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?

Sunapee Retreat | Fire Pit + Yard| Close to Lake: This vacation home near Windsor is located on a lake and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and 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 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.