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Windsor Vacation Rentals

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Vacation Rentals in Windsor

Studio Suite #2 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

9.8 out of 10, Exceptional, (6)
"Was a great location close to the mountain, comfortable and clean, an excellent stay. Walls were a bit thin, but others on property were respectful and quiet. Really enjoyed our stay for a weekend!"
The price is CA $273
CA $336 total
includes taxes & fees
Aug 11 - Aug 12
Studio Suite #2 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

Two Queen Bed Standard Hotel room with outdoor heated pool 201

8.6 out of 10, Excellent, (12)
"Our room was easy to find and very clean. And the late check-in was very helpful."
The price is CA $142
CA $216 total
includes taxes & fees
Aug 3 - Aug 4
Two Queen Bed Standard Hotel room with outdoor heated pool 201

Queen Studio on the 2nd floor with outdoor heated pool 207

8.0 out of 10, Very good, (5)
"Overall a good option for a visit to Killington if you don’t need to be on the access road. The outdoor heated pool was a really nice way to relax after a day of skiing. If you don’t want to drive, there is a pretty good restaurant across the street. The only slight concern is if more units than unit 207 are listed on VRBO (the unit we stayed in). I’m glad we had an upstairs unit because the floor was very squeaky. I was wondering if it was annoying the unit below us. With that minor detail...
The price is CA $142
CA $215 total
includes taxes & fees
Jul 27 - Jul 28
Queen Studio on the 2nd floor with outdoor heated pool 207

Cozy Cavendish Bunk minutes to Okemo

9.8 out of 10, Exceptional, (6)
"Very cozy and had all the essentials we needed for our trip! Check in and check out were easy, and it was perfect for our winter trip. It's a short drive to Okemo, which is super convenient - would definitely stay here again!"
The price is CA $173
CA $327 total
includes taxes & fees
Jul 16 - Jul 17
Cozy Cavendish Bunk minutes to Okemo

116 Two Double bed Standard Hotel room

8.6 out of 10, Excellent, (10)
"The place is good. It was our first time here and enjoyed our stay. The brook overlooking our window made the day"
The price is CA $142
CA $215 total
includes taxes & fees
Jul 21 - Jul 22
116 Two Double bed Standard Hotel room

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

9.4 out of 10, Exceptional, (16)
"We celebrated my sister's 80th birthday at Blueberry Hill. It was very quiet, pleasant and perfect for our family."
The price is CA $204
CA $693 total
includes taxes & fees
Jul 16 - Jul 17
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Modern Farm House…minutes to Okemo; 2 King beds!

9.4 out of 10, Exceptional, (10)
"We were a few families visiting for a ski weekend. Location was great and the house was clean, updated, and had plenty of space. Only thing we thought was inconvenient was the lack of spare TP! "
The price is CA $185
CA $583 total
includes taxes & fees
Jul 16 - Jul 17
Modern Farm House…minutes to Okemo; 2 King beds!

118 Two Double bed Standard Hotel room

9.0 out of 10, Wonderful, (2)
"We love staying here. So close to Killington, but also convenient. Clean, well maintained, and nicely furnished. Beautiful creek."
The price is CA $142
CA $215 total
includes taxes & fees
Aug 3 - Aug 4
118 Two Double bed Standard Hotel room

2 Bed/2 Bath Suite #5 at The Lodge | Minutes from Sunapee Harbor & Mt. Sunapee

9.8 out of 10, Exceptional, (12)
"Nice clean property.10-15 minutes from Mt. Sunapee.Nice bedrooms and the gameroom was a bonus for our kids."
The price is CA $432
CA $534 total
includes taxes & fees
Jul 21 - Jul 22
2 Bed/2 Bath Suite #5 at The Lodge | Minutes from Sunapee Harbor & Mt. Sunapee

Brook Road Condo

8.8 out of 10, Excellent, (14)
"Nice place close to the mountain!"
The price is CA $265
CA $482 total
includes taxes & fees
Jul 17 - Jul 18
Brook Road Condo

Main Street Retreat 4-bedroom w Hot Tub, Walk to Beach, Harbor & Restaurants

10.0 out of 10, Exceptional, (1)
"Very clean and well designed rental. The owner was very pleasant to work with. I would highly recommend this rental to anyone!!"
The price is CA $452
CA $1,069 total
includes taxes & fees
Jul 17 - Jul 18
Main Street Retreat 4-bedroom w Hot Tub, Walk to Beach, Harbor & Restaurants

Sleep Woodstock - 2 Double Beds - Dog Friendly

The price is CA $164
CA $234 total
includes taxes & fees
Jul 17 - Jul 18
Sleep Woodstock - 2 Double Beds - Dog Friendly

Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee

10.0 out of 10, Exceptional, (1)
"Immaculate property and centrally located.Great communication with host."
The price is CA $445
CA $892 total
includes taxes & fees
Jul 22 - Jul 23
Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee

Brook Road Condo

3.0 star property
8.8 out of 10, Excellent, (3)
The price is CA $284
CA $445 total
includes taxes & fees
Jul 16 - Jul 17
Brook Road Condo

CozyDen - AC, Grill, Bike to Mountain, Porch!

The price is CA $118
CA $383 total
includes taxes & fees
Jul 20 - Jul 21
CozyDen - AC, Grill, Bike to Mountain, Porch!

Lake Front Family Friendly Escape

10.0 out of 10, Exceptional, (2)
"What an amazing place! Very serene, clean and big enough for my family of 5. The hosts thought of everything to make our stay comfortable and memorable. Tough to beat the location! We will absolutely return!"
The price is CA $339
CA $712 total
includes taxes & fees
Jul 24 - Jul 25
Lake Front Family Friendly Escape

Chic Farmhouse Decor | Deck w/View

10.0 out of 10, Exceptional, (51)
"Great cabin about 2 minutes from Mt. Sunapee resort and state park, as well as several lake towns. Beds are extra comfortable and the kitchen has everything we needed. "
The price is CA $347
CA $681 total
includes taxes & fees
Jul 16 - Jul 17
Chic Farmhouse Decor | Deck w/View

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

2.0 star property
10.0 out of 10, Exceptional, (10)
"Great place, great host, great location!"
The price is CA $327
CA $844 total
includes taxes & fees
Jul 22 - Jul 23
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

The Grizz- AC, Pool, Sauna, Gym, Near Resort

10.0 out of 10, Exceptional, (4)
"Place was overall great and just as advertised. Beds were awesome including the Murphy bed. Thanks for a wonderful weekend! I would definitely stay again. "
The price is CA $154
CA $604 total
includes taxes & fees
Jul 23 - Jul 24
The Grizz- AC, Pool, Sauna, Gym, Near Resort

Fun In Fun Out Ski Home: Upper Unit. Renovated 3BR/2BA. Hot Tub. Sauna.

2.0 star property
10.0 out of 10, Exceptional, (1)
"Can’t beat the location convenient to the slopes and restaurants. The house was spotless. Every room has a thermostat. Loved the hot tub as well as the gas fireplace. Every day that it snowed someone was there to plow the lot and shovel the walkways and the decks. The discounted lift tickets were very easy to load and was the main reason for this rental. Would definitely rent this place in the future. "
The price is CA $217
CA $720 total
includes taxes & fees
Jul 16 - Jul 17
Fun In Fun Out Ski Home: Upper Unit. Renovated 3BR/2BA. Hot Tub. Sauna.
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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Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, we offer vacation rentals in Windsor close to The Sustainable Farmer, or you can select a more secluded option if you're looking for extra privacy while you relax. Windsor is known for its breweries and golf courses. Make sure you have time to check out the forests while you're in the area.

What's the top vacation rental that Windsor has to offer?

Quaint lakefront home with a private deck, firepit, and dock: Visitors like this Windsor vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Windsor?

With 9 Expedia vacation rentals, you're sure to find just the right place for your Windsor stay.

What can I see and do in Windsor?

Connecticut River and Paradise Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include The Sustainable Farmer. Other places in town to visit include Harpoon Brewery and Mt Ascutney State Park.

What are vacation rentals like in Windsor?

Vacation rentals are private properties you can stay in for several days or more in Windsor. Vacation rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family gatherings.