Windsor Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Windsor holiday rentals

Beach

Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
The price is HK$2,186
HK$4,054 total
includes taxes & fees
6 May - 7 May
Cabin on the hill Ascutney Vt - 4 bedrooms
Fridge, microwave, oven, stovetop

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
Sunapee
10.0 out of 10, Exceptional, (57 reviews)
"Our family had a wonderful stay at Soonipi Casa. Hosts were very welcoming and we enjoyed what was on the counter to welcome us. The accommodations were very comfortable and updated. So convenient to the Mountain!! 5 minutes. We had a memorable stay and will hope to do it again. "
United States
Ronald M.
The price is HK$1,403
HK$3,146 total
includes taxes & fees
5 May - 6 May
Chic Farmhouse Decor | Deck w/View
Exterior

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, (169 reviews)
"3rd year at this listing, absolutely love it. Close to okemo and mount snow. Host got back to me very quickly when reached out to. "
United States
Jake D.
The price is HK$1,332
HK$2,913 total
includes taxes & fees
5 May - 6 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Interior

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (36 reviews)
"Great location, so well set up with many extra touches inside "
United States
Victoria H.
The price is HK$1,234
HK$2,268 total
includes taxes & fees
5 May - 6 May
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Exterior detail

Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (15 reviews)
"Location was great"
United States
Andrew P.
The price is HK$1,332
HK$2,508 total
includes taxes & fees
5 May - 6 May
Brook Road Condo
Property grounds

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, (19 reviews)
"Our host went above and beyond to make our experience memorable. The house was very clean and we had a nice bottle of wine and snacks waiting for us. This house is close to the mountain and right near the lake. We will rent here again "
United States
Walter B.
The price is HK$1,481
HK$3,528 total
includes taxes & fees
7 May - 8 May
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Exterior

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, (22 reviews)
"The treehouse was the perfect place to unwind and relax for a few nights. Seeing the pines covered in snow out of every window was truly magical. Clean, well stocked, and everything was in good working order. "
United States
Ashley P.
The price is HK$1,410
HK$2,916 total
includes taxes & fees
7 May - 8 May
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Exterior

Luxury Treehouse Near Mount Sunapee | Fireplace + Deck

Luxury Treehouse Near Mount Sunapee | Fireplace + Deck
Newbury
10.0 out of 10, Exceptional, (30 reviews)
"Outstanding host and property—clean, beautiful, and really unique. Can’t wait to return!"
United States
Austin G.
The price is HK$1,869
HK$3,515 total
includes taxes & fees
6 May - 7 May
Luxury Treehouse Near Mount Sunapee | Fireplace + Deck
Property grounds

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

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
9.0 out of 10, Wonderful, (79 reviews)
"Unit was as advertised. Clean and comfortable."
United States
Ralph D.
The price is HK$588
HK$2,032 total
includes taxes & fees
5 May - 6 May
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
TV, fireplace, computer monitors

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.
The price is HK$2,051
HK$6,371 total
includes taxes & fees
5 May - 6 May
Elysium on Little Sunapee-Dock, Firepit, Trails
Terrace/patio

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, (8 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is HK$1,042
HK$2,325 total
includes taxes & fees
7 May - 8 May
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
TV

Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Location location location!"
United States
Britt H.
The price is HK$979
HK$3,249 total
includes taxes & fees
5 May - 6 May
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Living room

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
The price is HK$1,438
HK$2,343 total
includes taxes & fees
5 May - 6 May
Brook Road Cabin
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is HK$881
HK$2,376 total
includes taxes & fees
5 May - 6 May
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
TV

Brook Road Cabin

Brook Road Cabin
Goshen
9.8 out of 10, Exceptional, (17 reviews)
"Would go back!"
United States
Elizabeth C.
The price is HK$1,332
HK$2,423 total
includes taxes & fees
5 May - 6 May
Brook Road Cabin
Interior

Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
10.0 out of 10, Exceptional, (10 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is HK$1,042
HK$1,850 total
includes taxes & fees
26 May - 27 May
Addie's Place: A Quiet and Quirky Guesthouse
Indoor pool

Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (46 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is HK$580
HK$2,729 total
includes taxes & fees
5 May - 6 May
Resort condo with mountain views, full kitchen, and free WiFi
Interior

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.6 out of 10, Good, (56 reviews)
"The place was very dirty. The linens were dirty, the pots/pans and all of the cooking utensils were dirty. There was a rubber band on the floor in bathroom that didn't belong to us.There was only 3 forks and a few spoons. Very little silverwear."
United States
Leigh-Ellen F.
The price is HK$415
HK$2,299 total
includes taxes & fees
8 May - 9 May
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Smart TV, fireplace, books

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
The price is HK$1,114
HK$2,304 total
includes taxes & fees
6 May - 7 May
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Property grounds

Vermont Double Queen Suite | 10 Mins to Killington

Vermont Double Queen Suite | 10 Mins to Killington
Bridgewater
8.8 out of 10, Excellent, (5 reviews)
"This was perfect for our girls weekend! Great location, spacious & clean. Our host was so responsive & kind- highly recommend staying here when you visit Salem! "
United States
Brianna L.
The price is HK$627
HK$1,526 total
includes taxes & fees
5 May - 6 May
Vermont Double Queen Suite | 10 Mins to Killington
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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Staff was amazing. I didnt catch her name, but she was wonderful"
Candice 1-night trip
Posted 6 hours ago
Pointe at Castle Hill Resort

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals in Windsor close to Maze of Adventure, 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?

Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock: This holiday home rental outside of Windsor is located on a river, and has an outdoor pool, a fireplace and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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?

Connecticut River and Paradise Park are a couple of scenic spots to enjoy the outdoors, whereas American Precision Museum is one of the cultural attractions. Other places in town to visit include Harpoon Brewery and Mt Ascutney State Park.

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.