Search Windsor Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Windsor cottages

Property grounds

Charming 120-year-old farmhouse by the creek

Charming 120-year-old farmhouse by the creek
Hancock
9.0 out of 10, Wonderful, (24 reviews)
"Our family had a lovely time on this charming home. From someone who grew up in the Catskills, this was a wonderful getaway from the usual hustle & bustle life."
United States
Liza G.
The price is ￥22,539
￥49,819 total
includes taxes & fees
Mar 1 - Mar 2
Charming 120-year-old farmhouse by the creek
Exterior

Deluxe Duplex • Heart Runs & Ski Runs

Deluxe Duplex • Heart Runs & Ski Runs
Pleasant Mount
The price is ￥25,654
￥34,898 total
includes taxes & fees
Feb 22 - Feb 23
Deluxe Duplex • Heart Runs & Ski Runs
Exterior

Equestrian House Suites

Equestrian House Suites
3.0 star property
Pleasant Mount
The price is ￥31,070
￥91,289 total
includes taxes & fees
Feb 17 - Feb 18
Equestrian House Suites
Exterior

The Hideout Cottage • The Velvet Slopes of Romance

The Hideout Cottage • The Velvet Slopes of Romance
Pleasant Mount
The price is ￥17,774
￥47,783 total
includes taxes & fees
Feb 22 - Feb 23
The Hideout Cottage • The Velvet Slopes of Romance
Outdoor dining

Vacation Cottage Getaway • Crystal Peaks, Timeless Love

Vacation Cottage Getaway • Crystal Peaks, Timeless Love
Pleasant Mount
The price is ￥17,774
￥47,783 total
includes taxes & fees
Feb 22 - Feb 23
Vacation Cottage Getaway • Crystal Peaks, Timeless Love
Exterior

Forest Hideout Cottage • Valentine’s Grandeur in the Mountains

Forest Hideout Cottage • Valentine’s Grandeur in the Mountains
Pleasant Mount
10.0 out of 10, Exceptional, (1 review)
"the stay was fine, never knew there was a heated pool"
United States
Aliyah A.
The price is ￥31,334
￥89,905 total
includes taxes & fees
Feb 16 - Feb 17
Forest Hideout Cottage • Valentine’s Grandeur in the Mountains
Exterior

Cottage and Suite • Perfect Stay Close to Ski Slopes

Cottage and Suite • Perfect Stay Close to Ski Slopes
Pleasant Mount
The price is ￥30,235
￥80,806 total
includes taxes & fees
Feb 16 - Feb 17
Cottage and Suite • Perfect Stay Close to Ski Slopes
Exterior

Countryside Retreat Near Ski Slopes

Countryside Retreat Near Ski Slopes
Pleasant Mount
The price is ￥30,235
￥80,806 total
includes taxes & fees
Feb 16 - Feb 17
Countryside Retreat Near Ski Slopes
Exterior

City Escape • Close to Camps & ELK Ski

City Escape • Close to Camps & ELK Ski
Pleasant Mount
The price is ￥30,235
￥80,806 total
includes taxes & fees
Feb 21 - Feb 22
City Escape • Close to Camps & ELK Ski
Exterior

Woodland Hideout • Romantic Escape Close to Ski Trails

Woodland Hideout • Romantic Escape Close to Ski Trails
Pleasant Mount
The price is ￥30,235
￥80,806 total
includes taxes & fees
Feb 16 - Feb 17
Woodland Hideout • Romantic Escape Close to Ski Trails
Exterior

Family Cottage Escape • Group‑Friendly Retreat Close to Skiing

Family Cottage Escape • Group‑Friendly Retreat Close to Skiing
Pleasant Mount
The price is ￥30,235
￥80,806 total
includes taxes & fees
Feb 21 - Feb 22
Family Cottage Escape • Group‑Friendly Retreat Close to Skiing
Exterior

Country Escape • Near Camps & Ski

Country Escape • Near Camps & Ski
Pleasant Mount
The price is ￥34,816
￥87,067 total
includes taxes & fees
Feb 20 - Feb 21
Country Escape • Near Camps & Ski
Exterior

Family Cottage and Suite • Country Cottage Close to Ski Mountain

Family Cottage and Suite • Country Cottage Close to Ski Mountain
Pleasant Mount
The price is ￥34,816
￥87,067 total
includes taxes & fees
Feb 20 - Feb 21
Family Cottage and Suite • Country Cottage Close to Ski Mountain
Exterior

Premier Cottages & Suite • Cozy Cottage Near Ski Mountain

Premier Cottages & Suite • Cozy Cottage Near Ski Mountain
Pleasant Mount
The price is ￥47,642
￥128,153 total
includes taxes & fees
Feb 21 - Feb 22
Premier Cottages & Suite • Cozy Cottage Near Ski Mountain
Exterior

Family Suites •Close to Ski Runs Near Elk Mountain Ski Slopes

Family Suites •Close to Ski Runs Near Elk Mountain Ski Slopes
Pleasant Mount
The price is ￥59,187
￥132,391 total
includes taxes & fees
Feb 16 - Feb 17
Family Suites •Close to Ski Runs Near Elk Mountain Ski Slopes
Exterior

Premium Cottages and Suites • Mountain Retreat Near Ski Slopes

Premium Cottages and Suites • Mountain Retreat Near Ski Slopes
Pleasant Mount
The price is ￥60,286
￥145,303 total
includes taxes & fees
Feb 16 - Feb 17
Premium Cottages and Suites • Mountain Retreat Near Ski Slopes
Exterior

Family Cottage and Suite • Mountain Retreat Near Ski Slopes

Family Cottage and Suite • Mountain Retreat Near Ski Slopes
Pleasant Mount
The price is ￥63,951
￥150,150 total
includes taxes & fees
Feb 16 - Feb 17
Family Cottage and Suite • Mountain Retreat Near Ski Slopes
Exterior

Bring the Kids • Family Getaway Near Ski Trails

Bring the Kids • Family Getaway Near Ski Trails
Pleasant Mount
The price is ￥67,799
￥172,461 total
includes taxes & fees
Feb 22 - Feb 23
Bring the Kids • Family Getaway Near Ski Trails
Exterior

Premium Cottages and Suites • Near Camps & Ski

Premium Cottages and Suites • Near Camps & Ski
Pleasant Mount
The price is ￥86,123
￥192,534 total
includes taxes & fees
Feb 27 - Feb 28
Premium Cottages and Suites • Near Camps & Ski
Exterior

2BR Premium Duplex • The Velvet Slopes of Romance

2BR Premium Duplex • The Velvet Slopes of Romance
Pleasant Mount
9.0 out of 10, Wonderful, (2 reviews)
"Would've liked to have more to cook with than just a microwave, other than that the stay was commendable."
United States
Jeremy
The price is ￥21,073
￥57,003 total
includes taxes & fees
Feb 16 - Feb 17
2BR Premium Duplex • The Velvet Slopes of Romance
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Hampton Inn Binghamton/Johnson City

Hampton Inn Binghamton/Johnson City

10/10 Excellent
"Very kind and helpful staff. Great location for our needs. Clean rooms. "
Andrea 2-night trip
Posted 4 days ago
Hampton Inn Binghamton/Johnson City

Find out more about Windsor

Windsor Cottages information

Number of reviews
25
Accommodation
79 Cottages
Lowest Price
￥34,898
Highest Price
￥192,534

Frequently asked questions

Why book your cottage in Windsor with Expedia?
Expedia has some wonderful cottages in Windsor, so get set for a memorable vacay close to nature. If you have a fixed budget, choose how much you'd like to spend and the star rating of your property. Or, use our filters to search for cottages with a hot tub or free WiFi. We'll help you find the perfect digs whatever your plans or style of travel.
How can I find cheap cottages in Windsor?
Expedia is here to help you locate cheap cottages in Windsor. To discover the perfect stay in a couple of quick clicks, use the filter tool to refine your search results by budget, star rating and amenities.

Explore a world of travel with Expedia