Holiday Rentals in Windsor

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Windsor

Our top choices for Windsor holiday rentals

Handcrafted Riverfront Cabin on 10 acres

9.8 out of 10, Exceptional, (170)
"It was a great property. We all enjoyed walking around the property. Very comfortable. "
The price is €282
includes taxes & fees
30 Sept - 1 Oct
Handcrafted Riverfront Cabin on 10 acres

Cozy 2-bedroom cabin in Vestal NY

10.0 out of 10, Exceptional, (8)
" Beautiful landcape, quiet and secluded."
The price is €231
includes taxes & fees
7 Sept - 8 Sept
Cozy 2-bedroom cabin in Vestal NY

Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast

10.0 out of 10, Exceptional, (6)
"Charming cabin, newly built with outstanding attention to detail. Rachel was a wonderful host and very accommodating. We thoroughly enjoyed our stay and plan to return in the future."
Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast

Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River

10.0 out of 10, Exceptional, (184)
"Very nice!"
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River

Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.

2.0 star property
8.4 out of 10, Very good, (6)
"It was the perfect place for our small group. We just needed a place to sleep and shower overnight. The property was beautiful and we had a great time exploring. "
The price is €322
includes taxes & fees
6 Sept - 7 Sept
Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.

Riverfront Cabin West Branch Delaware River

9.8 out of 10, Exceptional, (114)
"This place is clean and host is great, I recommend "
Riverfront Cabin West Branch Delaware River

Spectacular Catskill Mountain River Front Custom Log Home

10.0 out of 10, Exceptional, (70)
"Great Location"
Spectacular Catskill Mountain River Front Custom Log Home

Quiet Lakefront Retreat nestled in the woods.

10.0 out of 10, Exceptional, (82)
"This cabin was just as advertised. The cabin was very clean, and all you would need for a comfortable stay was included. I very much enjoyed my two days there."
The price is €153
includes taxes & fees
11 Sept - 12 Sept
Quiet Lakefront Retreat nestled in the woods.

Breathtaking 44+ Acre Country Estate

10.0 out of 10, Exceptional, (36)
"Great place, great setup and property "
Breathtaking 44+ Acre Country Estate

Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing

10.0 out of 10, Exceptional, (40)
"Enjoyed our stay, unfortunately it rained so couldn’t enjoy the outside space. "
Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing

Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.

9.6 out of 10, Exceptional, (118)
"My family rented this cabin for a short ski trip to Elk mtn. The cabin was really nice and described nicely in summary. We couldn’t do much exploring of propety due to amount of snow but we are already looking forward to renting this in summer. It’s right on lake with a dock, couldn’t ask for anything better. We really enjoyed our visit. "
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.

Elk Mountain Vacation Home on 21 Acres

9.8 out of 10, Exceptional, (44)
"This home was cozy and welcoming. We thoroughly enjoyed our time here and highly recommend. "
Elk Mountain Vacation Home on 21 Acres

Rivers Edge of the West Branch Delaware River w Private Boat Launch

9.6 out of 10, Exceptional, (109)
"Great host and property! Look forward to another visit!"
Rivers Edge of the West Branch Delaware River w Private Boat Launch

Cabin on the Lake • Deck, Dock & Woods

8.0 out of 10, Very good, (1)
"Nice place tucked away in the woods. Great place to read and watch nature."
Cabin on the Lake • Deck, Dock & Woods

Secluded Summer Cabin Near Trails w/ Firepit, Hot Tub & Stargazing Views!

10.0 out of 10, Exceptional, (26)
"These cabins are super cute and essentially like a studio cabin set up. Bedroom/Living Area is sufficient, Bathroom is really good size & outdoor areas are a bonus!"
The price is €152
includes taxes & fees
14 Sept - 15 Sept
Secluded Summer Cabin Near Trails w/ Firepit, Hot Tub & Stargazing Views!

12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos

9.8 out of 10, Exceptional, (29)
"We really enjoyed our stay. The place is even better than the pictures and the host Julia was excellent."
12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos

Charming 120-year-old farmhouse by the creek

8.8 out of 10, Excellent, (23)
"Close to town ,clean just what we were looking for"
The price is €268
includes taxes & fees
1 Oct - 2 Oct
Charming 120-year-old farmhouse by the creek

Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY

9.8 out of 10, Exceptional, (129)
"We love the cabin. Just as described. Host Kelly was very helpful and communicative. "
The price is €321
includes taxes & fees
8 Sept - 9 Sept
Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY

Equestrian House Suites

3.0 star property
The price is €169
includes taxes & fees
10 Sept - 11 Sept
Equestrian House Suites

Indoor Pool,Largest Game Lodge,Sleeps 39

10.0 out of 10, Exceptional, (54)
"A group of us stayed for two nights and the property absolutely exceeded our expectations. Leah was a great communicator and I would absolutely recommend this property for a group to get away and enjoy all of the activities it has to offer."
Indoor Pool,Largest Game Lodge,Sleeps 39
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

Find out more about Windsor

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 €152 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. 

Explore a world of travel with Expedia

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay. Windsor is known for its parks and basketball games. Make sure you have time to check out the cafés and bars during your trip.

What are some of the best holiday rentals that Windsor has to offer?

Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.: This holiday home rental outside of Windsor is located in the mountains, and has a patio, a garden 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. Make the most of games in this rental home to help you unwind.

What’s there to see and do in Windsor?

Explore the area and cultural attractions such as Deposit Historical Museum, or visit one of the family-friendly sights such as Animal Adventure Park. Susquehanna River and West Branch Delaware River are a couple of places you'll find in the wider area.

What’s a holiday rental in Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.