Windsor Holiday Rentals from €174: Search Short-Term Rentals

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Holiday Rentals in Windsor

"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "

"A few weeks ago my partner and I stayed at the Hideway Cabin for the fifth year in a row. We made this a yearly tradition of ours. I cannot say enough about the place! The cabin very clean and cozy. The kitchen and bedrooms are stocked with all the necessities. It is located only a few, short minutes from Ludlow's center of town. The hot tub is amazing. I love seeing the stars shining bright at night. Highly recommend!"

"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 "

"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. "

"The area was amazing and the views were incredible. "

includes taxes & fees

25 Nov - 26 Nov

"We loved the condo and the easy walking avvess to all of what Killington offers! We would definitely stay here again! "

"Great weekend! Beautiful location !!"

"Accurate representation of the property. Check in was easy after some confusion as the access door is right next to another unit and not wanting to interfere with another group late at night. Owners were able to clarify and said they would put a better note into the welcome message to alleviate future confusion. Overall, good price and would stay again."

"The location of the property was great.. Centrally located to everything we wanted to see. I would have liked to have a vacuum or even a broom available. The place had a few areas that could have been cleaner. "

"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

22 Dec - 23 Dec

"We had a lovely time at the Arched Chalet for my family's annual vacation in Vermont. It was very comfortable, well-appointed, and in a great location. Even in the summer heat we did not need the AC - it was so comfortable with the fans and the lower level is naturally cool. Great location near Camp Plymouth (we went to the lake twice), and restaurants/shops in Ludlow and Woodstock."

"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!"

"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...

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

"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

23 Nov - 24 Nov

"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...

"This property was just what we were looking for in a weekend getaway in VT. Would highly recommend. "

"Our stay was wonderful, and the hosts were more than accomadating! Lovely home and very convenient to Ludlow and Okemo. "

"Very cute cabin in the woods. Less than 2 miles off of route 4, which made it easy to get anywhere in Vermont!"

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"Great experience! It was a lot of fun around the pool table or the fire pit outside. We loved it! It was great to have our dog with us everywhere around the hotel. Everything is very clean and in modern design. The only downside was that the restaurant dinner menu is limited to 5 options and there is no breakfast, just a Starbucks kiosk with coffee and muffins. We will go back! "

includes taxes & fees

9 Dec - 10 Dec

"So convenient to highway, but quiet area. Desk people were so helpful"

includes taxes & fees

22 Dec - 23 Dec

"Lovely hotel. Could do with some updates in areas but a very unique picturesque place . "

includes taxes & fees

16 Dec - 17 Dec

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 €174 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

"Nice hotel. High end but very nice. "

A verified traveller stayed at Hanover Inn Dartmouth

Posted 16 hours ago

5/5 Excellent

Great Accommodations

"First trip to Quechee and booked the Align Inn back in June for our November stay. Very happy with the accommodations. The person at the front desk was welcoming when we arrived and the lobby was large and very bright with the fireplace going. Our room was large and clean. The bed was comfortable and the included breakfast was plentiful. Loved the waffles. Tried out the pool which was nice with plenty of towels. Asked the desk clerk for dinner suggestions and she was right on with the two we tried. A short walk to the Quechee gorge, restaurants and antique shop. We would definitely return."

A verified traveller stayed at Align Inn Vermont

Posted 4 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?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: 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 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Beautiful Myrtle Beach Condo with Amenities Galore

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

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

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

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

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

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

Trail Creek 33 | Condo in Killington

Treehouse at Wise Pines- SoBo

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

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

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

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

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

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

Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

Idyllic Lakefront House Suited Two Families

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Other types of properties in Windsor you may be interested in

Killington Mountain Lodge, Tapestry Collection by Hilton

Hampton Inn White River Junction

Woodstock Inn & Resort

Find out more about Windsor

Recent reviews of Windsor properties

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Frequently asked questions