Windsor Vacation Rentals from ￥25,106: Search Short-Term Rentals

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

Idyllic Lakefront House Suited Two Families : You might want to consider this vacation home rental near Windsor, which is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 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.

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Vacation Rentals in Windsor

"very clean and easy to access close to mountain"

"The condo was very cozy for a family of four and suited us perfectly. Beds were comfortable and condo was clean. "

￥34,394 total

includes taxes & fees

Sep 29 - Sep 30

"Cozy but all the amenities, great location"

￥25,106 total

includes taxes & fees

Sep 29 - Sep 30

"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "

"This place was great for my family and I. It is very close to Okemo and town "

"Gorgeous log home , spacious, cozy , fun and comfortable ."

"Great time and great place"

"Terrific and comfortable place to stay! Amazing firepit!"

"Perfect location for a quick ski trip. "

￥36,627 total

includes taxes & fees

Sep 29 - Sep 30

"Convenient for skiing and visiting the greater VT area. Unit has what you need for your stay."

"Had a great time staying so close to Killington. Sauna, hot tub and pool were a great way to warm up after a day of skiing."

"We really enjoyed our stay at the lake house. We had great views of the lake and the kitchen was very well stocked. The beds were comfortable and the house was very clean and nicely decorated. Thank you for the incredible stay and we will be staying again!"

"Very relaxing stay! Cabins are beautiful, location is private and Wendi was very helpful with our stay"

￥48,930 total

includes taxes & fees

Oct 22 - Oct 23

"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"

"I had an amazing time with my family, I will definitely be coming back "

Solitude Village Two Bedroom Suite Mountainside | Private kitchen | Fridge, microwave, stovetop, toaster

"Beautiful Area. "

"Cute cabin close to Okemo and town! Really enjoyed our stay and would definitely return. "

"Great property, cozy and well maintained!"

"The property was as described, very clean, updated with a nice view. WeHad fun exploring the area.We enjoyed the fireplace while relaxing after hiking and exploring."

"Had a great stay, cozy log cabin, beds were very comfortable. So nice to have a few garbage bags, paper towels, soaps and toiletries!! Also some coffee filters:) Hot tub was great too! "

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Top Windsor Hotel Reviews

Fireside Inn & Suites West Lebanon

10/10 Excellent

"Fireside Inn was a warming place to stay in West Lebanon, NH. Our room was amazing and we will definitely consider staying there again if we ever visit NH."

Best Western West Lebanon-Hanover Hotel

10/10 Excellent

"The hotel is very nice and the staff is friendly. Our room was clean and the bed was comfortable. We stayed two nights and enjoyed the complimentary breakfast. I don't know the age of the hotel, but everything seemed fairly new. The bathroom mirror had great lighting."

Mountain Sports Inn

10/10 Excellent

"An absolutely amazing place to stay. The rooms I loved. I get so tired of the regular cookie cutter fancy hotel rooms. This is a ski lodge and it's designed and decorated as such. The staff is super friendly. There is adequate parking outside. It's in a beautiful area with restaurants and bars within driving distance The breakfast options were very plentiful Continental breakfast and it included fruit three different kinds of cereal a few different kinds of bagels muffins donuts there was some orange juice hot tea and coffee more than enough.. I will definitely be back it was a great place to stay and the beds were so comfortable It was one of the most comfortable beds I've ever slept in"

Find out more about Windsor

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Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, we offer vacation rentals in Windsor close to Path of Life Garden, 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?

Idyllic Lakefront House Suited Two Families: You might want to consider this vacation home rental near Windsor, which is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 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 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 Path of Life Garden 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.

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Windsor Vacation Rentals

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Vacation Rentals in Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Mountain Green

Mountain Green

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

Winterplace at Okemo

Winterplace at Okemo

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Beautifully renovated with fireplace and coffee bar

Beautifully renovated with fireplace and coffee bar

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Killington Retreat

Killington Retreat

Idyllic Lakefront House Suited Two Families

Idyllic Lakefront House Suited Two Families

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Treehouse at Wise Pines- SoBo

Treehouse at Wise Pines- SoBo

Okemo Mountain Lodging

Okemo Mountain Lodging

Solitude Village at Okemo

Solitude Village at Okemo

Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Top Windsor Hotel Reviews

Fireside Inn & Suites West Lebanon

Find out more about Windsor

Find out more about Windsor

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

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