Photo by William E Berry Jr.

Windsor Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
In two weeks

Vacation Rentals in Windsor

Mountain Green

2.0 star property
Killington
6.6 out of 10, (13)
"Wasnt clean and the front of the building looked terrible with the construction going on."
United States
Matthew
$230 nightly
The price is $253
Nov 9 - Nov 10
Total with taxes and fees
Mountain Green

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
Killington
9.0 out of 10, Wonderful, (53)
"Clean and beautiful scenery "
United States
David
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

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

Clock Tower Base Area
9.0 out of 10, Wonderful, (73)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
$224 nightly
The price is $253
Nov 10 - Nov 11
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

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

Ludlow
9.8 out of 10, Exceptional, (127)
"Enjoyed our stay immensely"
United States
jim m.
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Winterplace at Okemo

4.0 star property
Clock Tower Base Area
8.8 out of 10, Excellent, (25)
"I think it needs some wall touch ups and new shower liners , other than that is was a pleasant stay. "
United States
Jocelin
Winterplace at Okemo

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton
9.6 out of 10, Exceptional, (166)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
$321 nightly
The price is $360
Nov 10 - Nov 11
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

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

Andover
9.0 out of 10, Wonderful, (29)
"The property was beautiful with a gorgeous view. The cleanliness of the house was less than expected. Cobwebs, stained bedspread, dirty cabinets, and handprints all over the loft windows gave the impression that it hadn't been thoroughly cleaned in a while. There were also several lightbulbs that were burned out on arrival. If it were cleaned up properly, it would be a great place to stay."
United States
Stephen T.
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

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

Ludlow
8.0 out of 10, Very Good, (41)
"This Vrbo has been housing people since the 1960's, and we're so glad to be a part of this place's history It is truly a timeless home within a beautiful area with great outdoor activites, generous people and good food (we recommend The Hatchery). Both showers (the top floor shower and the middle floor) did have a leak, but our hosts responded quickly to our concerns and addressed them within a timely manner :) "
United States
John Q.
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning

Killington
8.4 out of 10, Very Good, (13)
"This house was fully equipped with everything we needed! Very spacious and cozy! It’s right in the heart of Killington with everything you need within reach! Grocery, gift shops, restaurants and lots of activities! We had a wonderful visit! And the adventure park was just. 10 minute drive! We will definitely be back! Thanks for everything!"
United States
Maura Y.
Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning

Beautifully renovated with fireplace and coffee bar

Hartford
10.0 out of 10, Exceptional, (127)
"It was a perfect place for our family! Exactly what you needed and felt cozy. They also surprised us with some local donuts - our kids had one at every breakfast! Thank you for your hospitality!"
United States
Lily H.
Beautifully renovated with fireplace and coffee bar

Killington 2 Story - Escape 2BR/2BA, Sleeps 6, Family & Friends Retreat w/ WiFi

2.0 star property
Killington
$280 nightly
The price is $316
Nov 10 - Nov 11
Total with taxes and fees
Killington 2 Story - Escape 2BR/2BA, Sleeps 6, Family & Friends Retreat w/ WiFi

Treehouse at Wise Pines- SoBo

Woodstock
9.8 out of 10, Exceptional, (24)
"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"
Canada
Victoria M.
$171 nightly
The price is $187
Nov 9 - Nov 10
Total with taxes and fees
Treehouse at Wise Pines- SoBo

Idyllic Lakefront House Suited Two Families

Ludlow
9.6 out of 10, Exceptional, (171)
"This was a great rental for our family. Lots to do nearby but the lake is where we spent most of our time - paddle boarding, kayaking and fishing. The swimming from the dock was not ideal but when we hopped on our paddle board it was very nice to swim in the central part the lake. Creemees at the sugar house were very good; also really enjoyed buttermilk falls and okemo."
United States
Robin C.
Idyllic Lakefront House Suited Two Families

Spacious 3BR Home Near Lake & Mountain - Sleeps 9 - Sunapee Retreat

2.0 star property
Newbury
Spacious 3BR Home Near Lake & Mountain - Sleeps 9 - Sunapee Retreat

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Ludlow
10.0 out of 10, Exceptional, (95)
"Our stay was great! Very nice cabin on the water with wood burning fireplace, fire pit, gas grill, and everything else you need for a pleasant get a way!"
United States
Jason B.
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Killington Chalet - Great Space and Location!

The Woods
9.6 out of 10, Exceptional, (15)
"Perfect for 5 guys who want to skiing. Close to 3 ski slopes. We cooked breakfast and dinner. Owner was super responsive."
United States
George F.
Killington Chalet - Great Space and Location!

Killington Retreat

2.0 star property
Killington
9.6 out of 10, Exceptional, (15)
"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."
United States
shawn c.
Killington Retreat

Solitude Village at Okemo

4.0 star property
Clock Tower Base Area
8.0 out of 10, Very Good, (31)
"Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also."
United States
Larry
Solitude Village at Okemo

The Racquetball House - Home to the BIGGEST hot tub in Killington!

Killington
9.6 out of 10, Exceptional, (67)
"We enjoyed the racquetball house more than we could have expected. It was a beautiful and clean space perfect for a family getaway."
United States
James S.
The Racquetball House - Home to the BIGGEST hot tub in Killington!

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

2.0 star property
Cavendish
10.0 out of 10, Exceptional, (9)
"Very relaxing stay! Cabins are beautiful, location is private and Wendi was very helpful with our stay"
United States
Nicholas M.
$285 nightly
The price is $310
Nov 11 - Nov 12
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $187 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: You might want to consider this vacation home rental near Windsor, which is located on a lake and has a fireplace, a balcony, 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 12 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.