Default HTG hotel image

Holiday Rentals in Windsor

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Windsor holiday rentals

1. Waterfront Properties vacation rental

Waterfront Properties vacation rental
Windsor
10.0 out of 10, Exceptional, (76 reviews)
"My family and I had a perfect weekend getaway at this beautiful property. Amy and her husband were extremely nice and helpful. We would definitely stay there again."
United States
KURT N.
The price is €326
includes taxes & fees
1 Dec - 2 Dec
Waterfront Properties vacation rental

2. Fireside Cabin at Osborne Creek

Fireside Cabin at Osborne Creek
Port Crane
9.8 out of 10, Exceptional, (22 reviews)
"Great location, great host, and great property. "
United States
Matthew A.
The price is €130
includes taxes & fees
16 Nov - 17 Nov
Fireside Cabin at Osborne Creek

3. Peaceful 5-Acre Country Retreat with Cali~King Bed, Fire Pit & Near Oneonta

Peaceful 5-Acre Country Retreat with Cali~King Bed, Fire Pit & Near Oneonta
Afton
9.6 out of 10, Exceptional, (7 reviews)
"Clean and cozy. Well-stocked and private. Really enjoyed the location and stay. Heat/air was amazing."
United States
Wes
The price is €223
includes taxes & fees
29 Nov - 30 Nov
Peaceful 5-Acre Country Retreat with Cali~King Bed, Fire Pit & Near Oneonta

4. 2 Full Beds | Non-Smoking, Mini Fridge

2 Full Beds | Non-Smoking, Mini Fridge
Binghamton
8.8 out of 10, Excellent, (3 reviews)
"A calm vibe filled the room with gentle heating that wasn't harsh or chilly, just right. Internet worked steadily during my visit without interruptions or slowdowns."
United States
Anonymous traveller
The price is €92
includes taxes & fees
1 Dec - 2 Dec
2 Full Beds | Non-Smoking, Mini Fridge

5. Cozy little house in Johnson City

Cozy little house in Johnson City
Johnson City
8.0 out of 10, Very good, (18 reviews)
"Second time staying here, everything was great!"
United States
Chad A.
The price is €98
includes taxes & fees
16 Nov - 17 Nov
Cozy little house in Johnson City

6. Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY

Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
Binghamton
9.8 out of 10, Exceptional, (145 reviews)
"A delightful weekend getaway.Kelly the owner went out of her way to make us comfortableAs soon as you walk in the front door you can smell the cleanliness and the essential oils.We loved the sunken jacuzzi, hot tub, multiple swings and all the twinkle lightsThe free continental breakfast was a bonus "
United States
Dawn N.
The price is €303
includes taxes & fees
16 Nov - 17 Nov
Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY

7. BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY

BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY
Greene
10.0 out of 10, Exceptional, (15 reviews)
"Property was beautiful would t change anything. Will definitely book again when we are in town."
United States
Lori
BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY

8. Olivia House is a old farm house that has been updated!

Olivia House is a old farm house that has been updated!
Susquehanna
10.0 out of 10, Exceptional, (54 reviews)
"We have now stayed a few times here. Every time has been nothing short of perfect!!"
United States
Anna E.
The price is €310
includes taxes & fees
16 Nov - 17 Nov
Olivia House is a old farm house that has been updated!

9. Horse Motel • RV Camping • Tent Camping • Horse Experiences PET FRIENDLY!

Horse Motel • RV Camping • Tent Camping • Horse Experiences PET FRIENDLY!
Port Crane
10.0 out of 10, Exceptional, (2 reviews)
"We pitched our tent in a beautiful, grassy field on the height of land with a breathtaking view of the valley below. No road noise or light pollution. The sunset and night stars were stunning. Our dog loved the field. Terrific value. Highly recommended."
United States
Wendy W.
Horse Motel • RV Camping • Tent Camping • Horse Experiences PET FRIENDLY!

10. Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly

Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly
Greene
10.0 out of 10, Exceptional, (21 reviews)
"Cozy, clean and comfortable."
United States
Lyn J.
The price is €142
includes taxes & fees
16 Nov - 17 Nov
Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly

11. Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!

Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
Thompson
10.0 out of 10, Exceptional, (18 reviews)
"This is the perfect place for you to come and relax. "
United States
Anabel P.
The price is €237
includes taxes & fees
16 Nov - 17 Nov
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!

12. Hale Eddy

Hale Eddy
2.0 star property
Hancock
The price is €300
includes taxes & fees
16 Nov - 17 Nov
Hale Eddy

13. Hilltop, relax and enjoy the Endless Mountains views

Hilltop, relax and enjoy the Endless Mountains views
Hallstead
9.2 out of 10, Wonderful, (15 reviews)
"We needed a place to stay for the 6 of us attending the funeral of our mother and this vintage home was the perfect place for us. It offered tranquil views which was just what we needed. "
United States
Paula M.
The price is €327
includes taxes & fees
16 Nov - 17 Nov
Hilltop, relax and enjoy the Endless Mountains views

14. Golf, Fish & Ski: Retreat w/ Game Room in Thompson

Golf, Fish & Ski: Retreat w/ Game Room in Thompson
Thompson
8.0 out of 10, Very good, (1 review)
"Took a couple hours to get response from the owner the back door of the patio does not lock. I’ve tried everything overall a nice place to stay good place and good environments in the area. Wish they did more mowing."
United States
Jacob M.
The price is €449
includes taxes & fees
22 Nov - 23 Nov
Golf, Fish & Ski: Retreat w/ Game Room in Thompson

15. Golf, Fish & Ski: Retreat w/ Game Room in Thompson

Golf, Fish & Ski: Retreat w/ Game Room in Thompson
3.0 star property
Thompson
The price is €455
includes taxes & fees
22 Nov - 23 Nov
Golf, Fish & Ski: Retreat w/ Game Room in Thompson

16. 1 King Bed | Non-Smoking, Mini Fridge

1 King Bed | Non-Smoking, Mini Fridge
Binghamton
10.0 out of 10, Exceptional, (3 reviews)
"We appreciated starting each day with coffee ready along with the large bed made for two people. Small things like free WiFi really boosted our experience."
United States
Anonymous traveller
The price is €87
includes taxes & fees
13 Dec - 14 Dec
1 King Bed | Non-Smoking, Mini Fridge

17. Cozy 2b apt 25mins from All Star Village & 44mins from Cooperstown Dreams Park

Cozy 2b apt 25mins from All Star Village & 44mins from Cooperstown Dreams Park
Bainbridge
9.6 out of 10, Exceptional, (5 reviews)
"Quick, easy,, very nice and welcoming. Great place to rest, relax and enjoy some peace of life."
United States
Christopher F.
The price is €155
includes taxes & fees
16 Nov - 17 Nov
Cozy 2b apt 25mins from All Star Village & 44mins from Cooperstown Dreams Park

18. 2 Full Beds | Mobility Access Tub Nsmk Fridge

2 Full Beds | Mobility Access Tub Nsmk Fridge
Binghamton
10.0 out of 10, Exceptional, (1 review)
"Quiet corridors ensured no interruptions from loud doors slamming or neighbors creating noise unlike other places I've recently visited"
United States
Anonymous traveller
2 Full Beds | Mobility Access Tub Nsmk Fridge

19. 2 Queen Beds | Non-Smoking, Mini Fridge

2 Queen Beds | Non-Smoking, Mini Fridge
Binghamton
10.0 out of 10, Exceptional, (2 reviews)
"Needed just a clean place near the highway, this fit fine for one night."
United States
Anonymous traveller
The price is €96
includes taxes & fees
1 Dec - 2 Dec
2 Queen Beds | Non-Smoking, Mini Fridge

20. Jack Cabin - Views, Hot Tub, Fire Pit & Outdoors!

Jack Cabin - Views, Hot Tub, Fire Pit & Outdoors!
Thompson
9.4 out of 10, Exceptional, (13 reviews)
"Cool place to chilaxx"
United States
Luis R.
The price is €237
includes taxes & fees
16 Nov - 17 Nov
Jack Cabin - Views, Hot Tub, Fire Pit & Outdoors!
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

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 €96 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. 

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?

Waterfront Properties vacation rental: This highly rated holiday home rental in Windsor is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. 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 Ross Park Zoo. 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.