Windsor Holiday Rentals

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Holiday Rentals in Windsor

Waterfront Properties vacation rental
9.8 out of 10, Exceptional, (65)
"The house was perfect for our weekend. We appreciated that it was spotless and that the beds were super comfortable. Thank you! "
The price is AU$496
includes taxes & fees
22 Oct - 23 Oct
Waterfront Properties vacation rental
Handcrafted Riverfront Cabin on 10 acres
10.0 out of 10, Exceptional, (174)
"Beautiful cabin on very nice property. Great place to just relax. "
The price is AU$465
includes taxes & fees
29 Oct - 30 Oct
Handcrafted Riverfront Cabin on 10 acres
Equestrian House Suites
3.0 star property
Equestrian House Suites
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River
10.0 out of 10, Exceptional, (188)
"The property was beautiful, quiet, clean, and comfortable. The hosts were friendly, accommodating, and helpful. I really enjoyed my time there."
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River
Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast
10.0 out of 10, Exceptional, (10)
"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
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
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.
9.6 out of 10, Exceptional, (120)
"We loved the privacy and enjoyed all the kayaks, boat and canoe. Perfect lake vacation, plan on making it a yearly trip."
The price is AU$622
includes taxes & fees
26 Oct - 27 Oct
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.
Rivers Edge of the West Branch Delaware River w Private Boat Launch
9.6 out of 10, Exceptional, (112)
"We stayed in the cabin for a weekend and used the boat launch to do an all day fishing trip. The cabin was great and the float was as well. Lovely place in a beautiful spot on the river!"
Rivers Edge of the West Branch Delaware River w Private Boat Launch
Cozy 2-bedroom cabin in Vestal NY
9.6 out of 10, Exceptional, (13)
"This beautiful cabin was an absolutely heavenly place to stay for a few days. It is as peaceful as it appears... Maybe even more so... And it was so lovely to fall asleep to the song of frogs, and enjoy the glow of fireflies from out on the wrap around deck.Thank you for a truly wonderful stay."
The price is AU$410
includes taxes & fees
19 Oct - 20 Oct
Cozy 2-bedroom cabin in Vestal NY
DISCOUNT LAST MINUTE Elk Mountain Estate Manor in beautiful PA-Groups and Events
9.8 out of 10, Exceptional, (95)
"We booked at the last minute due to another rental falling through. The booking process was smooth and Laura was a gracious and amazing host. The property is beautiful and spacious! We can’t wait to visit again "
DISCOUNT LAST MINUTE Elk Mountain Estate Manor in beautiful PA-Groups and Events
Spectacular Catskill Mountain River Front Custom Log Home
10.0 out of 10, Exceptional, (72)
"Great Location"
Spectacular Catskill Mountain River Front Custom Log Home
Breathtaking 44+ Acre Country Estate
10.0 out of 10, Exceptional, (36)
"We had a great family vacation here, coming in from various parts of the country. The fire pit, fishing, pickle ball, pool, hot tub, bald eagles, shooting stars and scenic views were just a few of the highlights! Gorgeous property and very responsive answers to questions etc "
Breathtaking 44+ Acre Country Estate
Steps from En-Joie Golf - 3BR Bungalow, Pet-Friendly w/ AC & WiFi
9.8 out of 10, Exceptional, (10)
"Wonderful house and location. The house was truly perfect for us! "
Steps from En-Joie Golf - 3BR Bungalow, Pet-Friendly w/ AC & WiFi
Elk Mountain Vacation Home on 21 Acres
9.8 out of 10, Exceptional, (45)
"It’s our 4th year at Union Dales at this property. Simply amazing, rustic clean house, nature, privacy, beautiful trails, peace and quiet. "
Elk Mountain Vacation Home on 21 Acres
Quiet Lakefront Retreat nestled in the woods.
10.0 out of 10, Exceptional, (88)
"Great Lake get away very nice property and great host!!! Will be back "
The price is AU$270
includes taxes & fees
20 Oct - 21 Oct
Quiet Lakefront Retreat nestled in the woods.
Riverfront Cabin West Branch Delaware River
9.8 out of 10, Exceptional, (116)
"Great lil place, great host, will stay again when visiting family who live in town. "
Riverfront Cabin West Branch Delaware River
Waterfront house on the upper most portion of the West Branch Delaware.
10.0 out of 10, Exceptional, (34)
"Nice family style place to stay. "
Waterfront house on the upper most portion of the West Branch Delaware.
Cabin on the Lake • Deck, Dock & Woods
9.4 out of 10, Exceptional, (3)
"Nice place tucked away in the woods. Great place to read and watch nature."
Cabin on the Lake • Deck, Dock & Woods
Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing
10.0 out of 10, Exceptional, (47)
"We had a great stay. House is adorable. Worked well for our group as we had a friend’s wedding in the area. Would stay again! "
Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing
Charming & Private Delaware Riverfront Home near Callicoon NY
9.8 out of 10, Exceptional, (186)
"Great times and amazing views."
Charming & Private Delaware Riverfront Home near Callicoon NY
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$270 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 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?

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

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.