Photo by William E Berry Jr.

Holiday Rentals in Windsor

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Holiday Rentals in Windsor

Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (175)
"It was very clean and area is beautiful. The pictures did not show inside stairs and i just had back surgery. It was very difficult for me on stairs. I wish i knew that before booking.. Also the couch in living room was terrible to sit in. If they remodeled the upstairs, i would stay again. Thank you"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (32)
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (30)
"My family really enjoyed this Lake House. The beautiful views of the lake were breathtaking. The house had everything we needed for preparing meals. The kitchen was functional and generally well equipped. The beds in the house were particularly comfortable. We enjoyed early morning coffee on the deck with perfect views of the lake. The location was great. Lots of wonderful hiking trials in close proximity. My only suggestion to the owners is to give the house a good deep cleaning. Nonetheless,...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
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1 bedroom, Internet
Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (9)
"This is an adorable spot! Super quiet, the treehouse is very unique, and moments away from downtown Woodstock. We’ll be back!"
The price is €174
per night
21 May - 22 May
Treehouse at Wise Pines- SoBo
Exterior
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
9.8 out of 10, Exceptional, (157)
"The place is beautiful and the stay was fantastic. It is up a couple mile hill/road from the center of town, just long enough to make you feel you are out of the hustle. The property presents very well. The rooms are large for private space with 2 common rooms that are just as large for group time. The one suggestion would be to add a check in book of information, including necessary passwords (WIFI) and local attractions/restaurants. We had much of this in the interaction with the host through...
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (140)
"Great little house to enjoy spending time with family and all that VT has to offer. Wonderful host, we will be back."
The price is €339
per night
20 May - 21 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
6 bedrooms, WiFi, bed sheets
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
9.6 out of 10, Exceptional, (69)
"This was our second stay at the condo. Can’t beat the convenience of ski in ski out and coming home for lunch. The owner, Ralph, is very quick at getting back with any questions. Highly recommend!"
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
Fridge, oven, stovetop, coffee/tea maker
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
8.6 out of 10, Excellent, (7)
"The home is charming, immaculate and amidst woods with no neighbors in eye or earshot. It is on a dirt road, so an awd vehicle is a good idea. A stream runs along the driveway. The Ottauquechee River is across the road. The bathroom is on the first floor, and bedrooms on the second floor. The smoke detector goes off if you saute on the stove. I recommend learning how to turn off a wired in smoke detector. You should open the kitchen window when you saute, because most of the smoke detectors...
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Fridge, microwave, oven, stovetop
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
9.8 out of 10, Exceptional, (15)
"Great location to restaurant and ski mountain"
The price is €272
per night
19 May - 20 May
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Property grounds
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (141)
"Ursula was super helpful and the location is very charming. Perfect spot for us!"
Idyllic Lakefront House Suited Two Families
Property grounds
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, (27)
"Spacious and well kept....everything needed for for a fantastic group ski trip! Check in a breeze with communication from the owner. We look forward to a return trip!"
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Studio | Aerial view
Killington Center Inn & Suites by Killington VR - Studios
3.0 star property
10.0 out of 10, Exceptional, (1)
"We loved our little unit. Everything was clean and very modern. We especially loved the electric fireplace. Would stay here again. "
Killington Center Inn & Suites by Killington VR - Studios
Smart TV, fireplace, books
Beautifully renovated with fireplace and coffee bar
10.0 out of 10, Exceptional, (57)
"Was just visiting Vermont to fish for the weekend so I didn’t need anything fancy but it was quite nice"
Beautifully renovated with fireplace and coffee bar
Lake
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
10.0 out of 10, Exceptional, (116)
"Great place to stay for an early spring ski trip and eclipse viewing (we drove north after checking out). Clean, cozy place and pet friendly for our small dog. Located on a quiet dirt road but close to Ludlow town center and Okemo for skiing. Not too far from Killington either (which is where we went to ski). Minor issue for me was the bed was a bit too soft for my liking but otherwise, great place and would consider again in future."
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Fridge, microwave, oven, stovetop
Lakefront home with amazing views, fireplace, firepit, & gas grill
9.8 out of 10, Exceptional, (58)
"Awesome house. Great location. I would stay there again for sure!"
Lakefront home with amazing views, fireplace, firepit, & gas grill
Property grounds
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
9.8 out of 10, Exceptional, (187)
"We had a lovely stay, the kayaks and canoe were the feature of one afternoon and we greatly enjoyed paddling around Lake Pauline and checking out both dam areas. The house is very clean and well maintained, we fell in love with all the windows and light coming in the bedroom across from the bathroom. The quick walk to the sugar house was a feature for my kids, they also loved having the wii in their room and playing Mario kart with their aunt/uncle."
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Interior
Lovely wooded home with deck, enclosed porch, & fireplace - dog-friendly
8.0 out of 10, Very good, (14)
"We enjoyed our stay. It is a beautiful property. The only complaint I have is the TV did not have any good channels. No news channels not cable etc.."
Lovely wooded home with deck, enclosed porch, & fireplace - dog-friendly
Fridge, microwave, oven, stovetop
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
9.4 out of 10, Exceptional, (27)
"Loved everything about it. Will look to book again"
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
Fridge, microwave, oven, stovetop
Lake Sunapee Gathering Place, Serene Restored Barn
10.0 out of 10, Exceptional, (6)
"We are so happy we chose this home to stay at. The house is even better in person than photos. The description is accurate and the location truly offers something for everyone. Well stocked and clean! Check in/out was very easy and hosts are very welcoming and easy to contact. We would definitely stay again and recommend to family and friends!"
Lake Sunapee Gathering Place, Serene Restored Barn
Outdoor dining
8BR 5Bath, spa, pool table, convenient spot 2 mi to lifts, 1/2 mi to restaurants
10.0 out of 10, Exceptional, (113)
"This house was everything we needed. Ample space for a large group. Tom and Carla were very responsive. Our group had a terrific experience!"
8BR 5Bath, spa, pool table, convenient spot 2 mi to lifts, 1/2 mi to restaurants
Don't see what you're looking for?
See all available properties in Windsor
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.

Other types of properties in Windsor you may be interested in

Terrace/patio
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
7.4 out of 10, Good, (1000)
"The spirit and ambiance of this hotel was amazing. Loved it"
The price is €124
per night
28 May - 29 May
Killington Mountain Lodge, Tapestry Collection by Hilton
Front of property – evening/night
Hotel Coolidge
3.0 star property
8.2 out of 10, Very good, (1001)
"Historic hotel! Awesome corner king room. Yes, trains go by regularly but we had no problems with the "toot toooot" bc of the RR tracks nearby. Non-smoking so theres a cute court yard out back you can go if needed, parking is there too... very convenient to Dartmouth Hitchcock also. For the price well worth it!"
The price is €106
per night
22 May - 23 May
Hotel Coolidge
Exterior
Hampton Inn White River Junction
2.5 star property
8.6 out of 10, Excellent, (1000)
"Nice hotel with convenient access on our travels"
The price is €147
per night
23 May - 24 May
Hampton Inn White River Junction
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.

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. 

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?

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in Windsor?

With 12 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 American Precision Museum and Harpoon Brewery.

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.

Recent reviews of Windsor properties
Expedia verified reviews

Align Inn Vermont

Align Inn Vermont

5/5 Excellent
"Really a great cozy place to stay. Was my 2nd time and i'll continue to be a repeat customer 👍👍"
A verified traveller stayed at Align Inn Vermont
Posted 1 day ago
Align Inn Vermont