Windsor Holiday Rentals

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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Windsor holiday rentals

Property grounds

Waterfront Properties vacation rental

Waterfront Properties vacation rental
Windsor
9.8 out of 10, Exceptional, (67 reviews)
"The owners were very attentive and willing to answer any question we had with very quick responses. The owners gave many recommendations for food in the area when asked. The place fit our needs perfectly. Will rent this place again if in the area again."
United States
Tyler J.
The price is HK$979
HK$2,496 total
includes taxes & fees
25 Apr - 26 Apr
Waterfront Properties vacation rental
Exterior

Equestrian House Suites

Equestrian House Suites
3.0 star property
Pleasant Mount
The price is HK$1,147
HK$4,196 total
includes taxes & fees
29 Apr - 30 Apr
Equestrian House Suites
Terrace/patio

Equinunk

Equinunk
2.0 star property
Equinunk
The price is HK$1,700
HK$3,106 total
includes taxes & fees
30 Apr - 1 May
Equinunk
Property grounds

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, (14 reviews)
"This is the perfect place for you to come and relax. "
United States
Anabel P.
The price is HK$979
HK$1,583 total
includes taxes & fees
5 May - 6 May
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
TV, fireplace

Lake View Log Cabin with amazing views

Lake View Log Cabin with amazing views
Hancock
The price is HK$2,820
HK$5,445 total
includes taxes & fees
26 Apr - 27 Apr
Lake View Log Cabin with amazing views
Outdoor dining

King Cabin Secluded Romantic Space Near Elk Mountain. Hot Tub, Firepit & Views!

King Cabin Secluded Romantic Space Near Elk Mountain. Hot Tub, Firepit & Views!
Thompson
9.8 out of 10, Exceptional, (41 reviews)
"Great stay especially for a wedding for family vacation "
United States
Catherine P.
The price is HK$979
HK$1,583 total
includes taxes & fees
5 May - 6 May
King Cabin Secluded Romantic Space Near Elk Mountain. Hot Tub, Firepit & Views!
Exterior detail

Handcrafted Riverfront Cabin on 10 acres

Handcrafted Riverfront Cabin on 10 acres
Starlight
10.0 out of 10, Exceptional, (201 reviews)
"Comfortable and clean. "
United States
Pattie D.
The price is HK$1,057
HK$2,757 total
includes taxes & fees
5 May - 6 May
Handcrafted Riverfront Cabin on 10 acres
Interior

Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!

Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
Thompson
10.0 out of 10, Exceptional, (15 reviews)
"Perfect place to bring the family for a quiet ski holiday. "
United States
Pamela S.
The price is HK$1,253
HK$2,255 total
includes taxes & fees
28 Apr - 29 Apr
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
Exterior

Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY

Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
Binghamton
9.8 out of 10, Exceptional, (137 reviews)
"Warm, comfortable, welcoming house. The owner was very helpful and communicative. The hot tub was glorious. we loved it!"
United States
sandra s.
The price is HK$1,121
HK$2,576 total
includes taxes & fees
26 Apr - 27 Apr
Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
Smart TV

Seasons on Oak Short walk to best Fly Fishing in Northeast Cozy Cabin Deposit NY

Seasons on Oak Short walk to best Fly Fishing in Northeast Cozy Cabin Deposit NY
Deposit
10.0 out of 10, Exceptional, (19 reviews)
"A couple of our crew stayed here for the last couple weeks while out of town working on a job, and the cabin felt like home, it was clean, the host was super responsive, and it was just the perfect place for us. "
United States
RHL C.
The price is HK$2,154
HK$2,990 total
includes taxes & fees
27 Apr - 28 Apr
Seasons on Oak Short walk to best Fly Fishing in Northeast Cozy Cabin Deposit NY
Smart TV, fireplace, books, music library

Quiet Lakefront Retreat nestled in the woods.

Quiet Lakefront Retreat nestled in the woods.
Montrose
10.0 out of 10, Exceptional, (95 reviews)
"Great clean, comfortable place, attentive hosts, beautiful location. "
United States
David A.
The price is HK$1,018
HK$1,489 total
includes taxes & fees
5 May - 6 May
Quiet Lakefront Retreat nestled in the woods.
Interior

Charming 120-year-old farmhouse by the creek

Charming 120-year-old farmhouse by the creek
Hancock
9.0 out of 10, Wonderful, (25 reviews)
"Close to town ,clean just what we were looking for"
United States
Anonymous traveller
The price is HK$1,093
HK$2,520 total
includes taxes & fees
25 Apr - 26 Apr
Charming 120-year-old farmhouse by the creek
Property grounds

Susquehanna Waterfall Haven

Susquehanna Waterfall Haven
Susquehanna
The price is HK$1,586
HK$2,906 total
includes taxes & fees
5 May - 6 May
Susquehanna Waterfall Haven
Fridge, microwave, oven, stovetop

Family Cottage and Suite • Spring Days, Bright Nights

Family Cottage and Suite • Spring Days, Bright Nights
Pleasant Mount
The price is HK$3,280
HK$7,702 total
includes taxes & fees
25 Apr - 26 Apr
Family Cottage and Suite • Spring Days, Bright Nights
Property grounds

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

Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.
Hallstead
9.0 out of 10, Wonderful, (9 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 HK$1,762
HK$2,969 total
includes taxes & fees
25 Apr - 26 Apr
Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.
Exterior detail

Cozy little house in Johnson City

Cozy little house in Johnson City
Johnson City
8.6 out of 10, Excellent, (14 reviews)
"Good place to stay for graduation weekend. "
United States
Steven
The price is HK$634
HK$894 total
includes taxes & fees
26 Apr - 27 Apr
Cozy little house in Johnson City
1 bedroom, iron/ironing board, WiFi, bed sheets

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, (9 reviews)
"Very nice clean, right in the center of town, convenient to shops on restaurants. "
United States
Laura P.
The price is HK$713
HK$1,219 total
includes taxes & fees
18 May - 19 May
BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY
Private kitchen

Spacious 7-bedroom House in Vestal

Spacious 7-bedroom House in Vestal
Vestal
The price is HK$7,049
HK$13,143 total
includes taxes & fees
29 Apr - 30 Apr
Spacious 7-bedroom House in Vestal
Property grounds

Cozy 2-bedroom cabin in Vestal NY

Cozy 2-bedroom cabin in Vestal NY
Vestal
9.6 out of 10, Exceptional, (15 reviews)
"Host was absolutely amazing great people. Everything as expected in pictures and just a beautiful place to stay"
United States
Gregory G.
The price is HK$1,057
HK$1,814 total
includes taxes & fees
21 May - 22 May
Cozy 2-bedroom cabin in Vestal NY
Terrace/patio

Lakefront! Hot Tub-Sauna-Cold Tubs-SUPs-Bikes-Canoe-Kayak-Sundeck-Firepit-Dock!

Lakefront! Hot Tub-Sauna-Cold Tubs-SUPs-Bikes-Canoe-Kayak-Sundeck-Firepit-Dock!
Hancock
10.0 out of 10, Exceptional, (1 review)
"The cottage was so cute and lovely! It was everything we were looking for and plan to return again next year! "
United States
Morgan S.
The price is HK$2,766
HK$5,300 total
includes taxes & fees
30 Apr - 1 May
Lakefront! Hot Tub-Sauna-Cold Tubs-SUPs-Bikes-Canoe-Kayak-Sundeck-Firepit-Dock!
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

Microtel Inn & Suites By Wyndham Binghamton

Microtel Inn & Suites By Wyndham Binghamton

8/10 Good
"A basic room for the night. Price was good but no place to sit in a single bed room. Must always ask for two beds unless you want to watch TV from bed...I don't! The puff that served a a blanket was very short....not good for 2 people in a Queen bed. Breakfast was very good for a continental. Staff tried hard to accommodate."
Susan 1-night trip
Posted 1 hour ago
Microtel Inn & Suites By Wyndham Binghamton

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
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  • 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 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?

Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing: This holiday home rental outside of Windsor is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.