Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

Addie's Place: A Quiet and Quirky Private Guesthouse

Addie's Place: A Quiet and Quirky Private Guesthouse
Hartford
10.0 out of 10, Exceptional, (4 reviews)
"Perfect size and location! "
United States
Lyn H.
$167 nightly
The price is $189
Jan 28 - Jan 29
Total with taxes and fees
Addie's Place: A Quiet and Quirky Private Guesthouse

Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo
Woodstock
9.6 out of 10, Exceptional, (15 reviews)
"The treehouse was so cool and well maintained. We were very warm and everything was clearly laid out for where to go, where to park, etc. "
United States
Ethan
$172 nightly
The price is $188
Jan 28 - Jan 29
Total with taxes and fees
Treehouse at Wise Pines- NoBo

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
$684 nightly
The price is $752
Feb 8 - Feb 9
Total with taxes and fees
The Suites at Killington Center

Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.8 out of 10, Good, (9 reviews)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
$282 nightly
The price is $306
Jan 29 - Jan 30
Total with taxes and fees
Brook Road Cabin

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

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (11 reviews)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
$275 nightly
The price is $299
Jan 28 - Jan 29
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (6 reviews)
"Cabin was spotless and exactly what I expected"
United States
mark g.
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (166 reviews)
"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
$330 nightly
The price is $370
Feb 2 - Feb 3
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Newbury
10.0 out of 10, Exceptional, (17 reviews)
"Loved staying at this quaint cottage, the outside spaces were lovely and it was very clean! Communication with the owner was seamless and they were fantastic to deal with. I would highly recommend a stay here! "
United States
Lisa P.
$419 nightly
The price is $455
Jan 28 - Jan 29
Total with taxes and fees
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Newport
9.8 out of 10, Exceptional, (19 reviews)
"The tree house was just as pictured, beautiful inside and we had great views of the River. It was a great trip and we look forward to coming back!"
United States
Kimberly R.
$345 nightly
The price is $374
Jan 28 - Jan 29
Total with taxes and fees
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Clean & bright condo with mountain views & modern kitchen - walk to lifts

Clean & bright condo with mountain views & modern kitchen - walk to lifts
Killington
7.2 out of 10, Good, (45 reviews)
"Perfect place for a long weekend"
United States
Patrick D.
$249 nightly
The price is $281
Feb 10 - Feb 11
Total with taxes and fees
Clean & bright condo with mountain views & modern kitchen - walk to lifts

Elysium on Little Sunapee-Dock, Firepit, Trails

Elysium on Little Sunapee-Dock, Firepit, Trails
New London
9.8 out of 10, Exceptional, (12 reviews)
"Great Lake house with all the amenities you need for a great week!! Kitchen is well stocked. Wonderful hosts!"
United States
Caren H.
$673 nightly
The price is $731
Jan 28 - Jan 29
Total with taxes and fees
Elysium on Little Sunapee-Dock, Firepit, Trails

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Chester
10.0 out of 10, Exceptional, (11 reviews)
"We had a really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!"
United States
Carla C.
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Comfortable stay, great location. "
United States
Marjana
$327 nightly
The price is $349
Jan 28 - Jan 29
Total with taxes and fees
Luxury Condo Tucked in the Heart of Killington

Brook Road Cabin

Brook Road Cabin
Goshen
9.8 out of 10, Exceptional, (17 reviews)
"Would go back!"
United States
Elizabeth C.
$296 nightly
The price is $321
Jan 29 - Jan 30
Total with taxes and fees
Brook Road Cabin

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.4 out of 10, Good, (55 reviews)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
$319 nightly
The price is $361
Feb 3 - Feb 4
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (9 reviews)
"We loved staying here. It was comfortable, had everything we needed. 100% would stay here again!"
United States
Vanessa O.
$305 nightly
The price is $345
Feb 3 - Feb 4
Total with taxes and fees
Killington condo 5 min to killington resort

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

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
8.4 out of 10, Very Good, (35 reviews)
"Great stay!"
United States
Bryann F.
$291 nightly
The price is $329
Jan 28 - Jan 29
Total with taxes and fees
Comfortable mountain gem with pool, mountain views, & indoor parking space

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
Sunapee
10.0 out of 10, Exceptional, (51 reviews)
"Loved our stay and will definitely return!"
United States
Jenifer S.
$393 nightly
The price is $426
Jan 28 - Jan 29
Total with taxes and fees
Chic Farmhouse Decor | Deck w/View

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Plymouth
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay! Beautiful spot tucked in the woods. Great host communication!"
United States
Julie-Anne B.
$594 nightly
The price is $665
Feb 9 - Feb 10
Total with taxes and fees
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Mountain Green

Mountain Green
2.0 star property
Killington
7.0 out of 10, Good, (19 reviews)
"Great !"
United States
Raul
$271 nightly
The price is $298
Feb 10 - Feb 11
Total with taxes and fees
Mountain Green
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.
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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 $268 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 The Sustainable Farmer, 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?

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable: Visitors like this Windsor vacation home rental. It is located in the city center and has a fireplace, a patio, and laundry facilities to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a hot tub.

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 Paradise Park 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.