Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

The price is AU$731
includes taxes & fees
15 Mar - 16 Mar
Cabin on the hill Ascutney Vt - 4 bedrooms
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
The price is AU$269
includes taxes & fees
16 Mar - 17 Mar
Treehouse at Wise Pines- NoBo
9.6 out of 10, Exceptional, (167 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
The price is AU$525
includes taxes & fees
9 Mar - 10 Mar
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
10.0 out of 10, Exceptional, (7 reviews)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Holiday Home in Sunapee

Chic Farmhouse Decor | Deck w/View
10.0 out of 10, Exceptional, (55 reviews)
"Loved our stay and will definitely return!"
United States
Jenifer S.
The price is AU$631
includes taxes & fees
15 Mar - 16 Mar
Chic Farmhouse Decor | Deck w/View
9.8 out of 10, Exceptional, (21 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.
The price is AU$523
includes taxes & fees
8 Mar - 9 Mar
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
10.0 out of 10, Exceptional, (18 reviews)
"We loved our weekend experience at the Hideaway! "
United States
Benjamin M.
The price is AU$644
includes taxes & fees
18 Mar - 19 Mar
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
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 AU$995
includes taxes & fees
11 Mar - 12 Mar
Elysium on Little Sunapee-Dock, Firepit, Trails
10.0 out of 10, Exceptional, (14 reviews)
"This was absolutely perfect. Every part of the cabin was well thought out from design to decor. We had such an amazing time and already want to plan another getaway to this place. "
United States
Adam B.
The price is AU$490
includes taxes & fees
7 Apr - 8 Apr
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
10.0 out of 10, Exceptional, (7 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is AU$331
includes taxes & fees
23 Mar - 24 Mar
Addie's Place: A Quiet and Quirky Guesthouse

Cabin in Goshen

Brook Road Cabin
9.8 out of 10, Exceptional, (17 reviews)
"Would go back!"
United States
Elizabeth C.
The price is AU$467
includes taxes & fees
15 Mar - 16 Mar
Brook Road Cabin
10.0 out of 10, Exceptional, (20 reviews)
"Couple day getaway, beautiful views right on the water plenty of windows, well stocked on house essentials"
United States
Stephanie V.
The price is AU$871
includes taxes & fees
11 Mar - 12 Mar
Charming Lakefront Cottage on Lake Mascoma
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 AU$311
includes taxes & fees
11 Mar - 12 Mar
Vermont Double Queen Suite | 10 Mins to Killington
7.6 out of 10, Good, (56 reviews)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
The price is AU$454
includes taxes & fees
7 Apr - 8 Apr
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Holiday Home in Goshen

Brook Road Condo
3.0 star property
8.8 out of 10, Excellent, (3 reviews)
"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."
United States
Margaret
The price is AU$426
includes taxes & fees
8 Mar - 9 Mar
Brook Road Condo

Holiday Home in Newbury

Unique Treehouse Near Mt Sunapee
10.0 out of 10, Exceptional, (28 reviews)
"Great stay. Had a wonderful time."
United States
Chris P.
The price is AU$641
includes taxes & fees
8 Mar - 9 Mar
Unique Treehouse Near Mt Sunapee
9.0 out of 10, Wonderful, (78 reviews)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is AU$396
includes taxes & fees
7 Apr - 8 Apr
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
9.2 out of 10, Wonderful, (28 reviews)
"Overall very clean and nice. Needs some updating like more spoons, only 2, bigger coffee cups. And a new coffee table that is very worn. "
United States
David A.
The price is AU$373
includes taxes & fees
7 Apr - 8 Apr
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful studio, clean, safe and extremely convenient if you’re going to local shops, restaurants or killington to ski! Easy to check in and out and the staff was very friendly, accessible and accommodating! Would recommend:)"
United States
Maggie M.
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
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 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, 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 favourite 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 depend 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 AU$331 per night. Entering your travel dates in the search wizard might find you 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 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?

Idyllic Lakefront House Suited Two Families: This holiday home rental outside 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 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 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.