Windsor Holiday Rentals from €186: Search Short-Term Rentals

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Holiday Rentals in Windsor

"very clean and easy to access close to mountain"

includes taxes & fees

5 Jan - 6 Jan

"This was a really nice spacious property. It was very clean and in a nice location. "

"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "

"The tiny houses were cute and well equipped. They were ideal for 2 friends traveling together having their own space. I would definitely rent this property again. Only negative was having 3 empty propane tanks when we wanted to use the fire table(something to be added to the maintenance checklust) however once i text them they dropped a fresh tank off that same evening."

includes taxes & fees

5 Jan - 6 Jan

"Property was nice. Great pool area. "

"All in all it was a great trip. The place was very cute and as described. The upstairs bedrooms are not for light sleepers as the walls only go so far up so they are not really divided. I had read this in other reveiws but honestly for us it wasn't a problem. We went as a family group and it was kind of nice to be able to lay in bed and talk to the others in the room next to you. When we got there the hot tub was so hot that we were not able to get in. Maybe a problem with the thermostat but...

"Great weekend! Beautiful location !!"

"Amazing, thank you!"

"Great"

includes taxes & fees

20 Jan - 21 Jan

"We were a bit disappointed with this property. The pictures are a bit misleading as it felt dark and stuffy, which we didn’t expect. There was a strong cigarette odor that was hard to adjust to and the room kept dropping down to very cold temperatures (50s) even after we adjusted the thermostat. This was stressful since we have a 15 month old and were worried about her being too cold all night. The deck was completely blocked by a mound of treacherous ice from water dripping off the roof, which...

"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "

"The property was exactly as advertised and clean. The pool was open and it was a good option to relax. The acces to parking was terrible - muddy, sandy, icy gravel. It is clear that nobody was thinking about this at all. The access to lifts was not ski in/out, but shuttle was great, and running all time! There was a ski locker, which was convenient, though nobody told us about it and we figured it out ourselves. Card for pool did not work but the office was open and provided the correct one,...

includes taxes & fees

5 Jan - 6 Jan

"Gorgeous property with everything that we needed! It was relaxing and comfortable for everyone. The kids had a blast! The property management team was great with communication and offered early check in and late check out. Would absolutely stay here again!"

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

"Property was great and was clean with exception of the shower curtain that could use replacing but other than that it was great. We would stay again."

"We loved the cabin and its proximity to the town of Woodstock. Nice to come home at the end of the day. The only issue is the bedrooms are upstairs and the bathroom is downstairs….but we managed. Overall a great stay. "

"Never could get the wifi to work. I entered the code on the router 6 times but no luck. Would be helpful if you changed the password for the wifi to an easily entered name. The man who came to shovel unfortunately after we were stuck in the snow was very helpful and very nice.. He got us out."

includes taxes & fees

6 Jan - 7 Jan

"Beautiful property and wonderful host. Very welcoming and cozy, and within a quick drive of lots of great activities. I would definitely stay here again!"

includes taxes & fees

6 Jan - 7 Jan

"Stay was good. Couldn’t figure out the TV - Not sure if there was actually cable or not. Close to the main road so traffic was a bit loud. Other than that great stay. "

includes taxes & fees

14 Jan - 15 Jan

"Dishes were dirty, that's the plates, pots, pans, silverware, glasses, and cooking utensils. Parking garage was great. The dish washer leaked only to find out it was broken."

includes taxes & fees

8 Jan - 9 Jan

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Other types of properties in Windsor you may be interested in

"Staff is very friendly. It was clean but very old for a Hilton. The AC to the gym never worked and for the quality it seems overpriced buybinthinknits bc it's close to the ski resort. It definitely needs to be more updated . Overall, it's just ok when I compare to other Hilton's. Usually other Hilton's have a special lounge with appetizers and drinks for Gold members but this one doesn't. "

includes taxes & fees

8 Jan - 9 Jan

Combined shower/bathtub, eco-friendly toiletries, hair dryer, towels

"The hotel staff is awesome, super very nice people, it makes you feel really welcome when you arrive, and during the stay. The rooms are cozy, recently renovated and clean. Recommended!!!!"

includes taxes & fees

17 Jan - 18 Jan

"Our favorite lodge to stay at in Killington for many years! "

includes taxes & fees

12 Jan - 13 Jan

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as €186 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday 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 holiday.

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.

Recent reviews of Windsor properties

5/5 Excellent

"We chose to stay at the Hilton after other plans fell through. The location is safe and convenient off of 89. The staff were great and very chill which I always appreciate. The pool was warm enough (small) but open from 5AM-11PM which was a major score for New Years Eve with children. If we do a close getaway for a special occasion again, we will stay again!"

A verified traveller stayed at Hilton Garden Inn Hanover Lebanon

Posted 2 days ago

5/5 Excellent

Many thanks!

"This is a very convenient location. There is a grocery store across the street and the shops of Woodstock are a 5 minute walk. I also appreciate how the staff worked with my recent knee injury. They got me a downstairs room with a walk-in shower so I could avoid further injury. An excellent stay overall!"

A verified traveller stayed at The Shire Woodstock

Posted 7 days ago

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals in Windsor close to The Sustainable Farmer, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Windsor has to offer?

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location: This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Windsor?

With 11 Expedia holiday rentals, you're guaranteed to find just the right place for your Windsor stay.

What can I see and do in Windsor?

Mt Ascutney State Park and Connecticut River 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 American Precision Museum.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature amenities such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.

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Holiday Rentals in Windsor

Check Windsor holiday rental availability

Holiday Rentals in Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Beautiful Myrtle Beach Condo with Amenities Galore

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

Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

Amazing Mountain Condo - Right across the street to Killington Resort

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

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Beautifully renovated with fireplace and coffee bar

Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

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

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

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

Ski-in/ski-out condo with W/D, indoor pool, & hot tub

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Treehouse at Wise Pines- SoBo

Efficient condo near slopes with kitchenette & great location

Comfortable mountain gem with pool, mountain views, & indoor parking space

Other types of properties in Windsor you may be interested in

Killington Mountain Lodge, Tapestry Collection by Hilton

Align Inn Vermont

North Star Lodge and Resort

Find out more about Windsor

Recent reviews of Windsor properties

Hilton Garden Inn Hanover Lebanon

Greenbrier Inn

Super 8 by Wyndham White River Junction

Pointe at Castle Hill Resort

Summit Lodge

Fireside Inn & Suites West Lebanon

Align Inn Vermont

Hotel Coolidge

The Shire Woodstock

Frequently asked questions