Search Windsor Cottages

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Windsor cottages

Property grounds
Charming 120-year-old farmhouse by the creek

Charming 120-year-old farmhouse by the creek

Charming 120-year-old farmhouse by the creek
Hancock
8.8 out of 10, Excellent, (23)
"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.
$279 nightly
The price is $307
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming 120-year-old farmhouse by the creek
Outdoor dining
Deluxe Duplex • Near Camps & ELK Ski

Deluxe Duplex • Near Camps & ELK Ski

Deluxe Duplex • Near Camps & ELK Ski
Pleasant Mount
$212 nightly
The price is $229
Dec 22 - Dec 23
Total with taxes and fees
Deluxe Duplex • Near Camps & ELK Ski
Exterior
Equestrian House Suites

Equestrian House Suites

Equestrian House Suites
3.0 star property
Pleasant Mount
$531 nightly
The price is $579
Jan 4 - Jan 5, 2026
Total with taxes and fees
Equestrian House Suites
Outdoor dining
Vacation Cottage Getaway • Close to Ski Mountain

Vacation Cottage Getaway • Close to Ski Mountain

Vacation Cottage Getaway • Close to Ski Mountain
Pleasant Mount
$306 nightly
The price is $331
Jan 4 - Jan 5, 2026
Total with taxes and fees
Vacation Cottage Getaway • Close to Ski Mountain
Exterior
The Hideout Cottage • Near Camps & ELK Ski

The Hideout Cottage • Near Camps & ELK Ski

The Hideout Cottage • Near Camps & ELK Ski
Pleasant Mount
$297 nightly
The price is $322
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Hideout Cottage • Near Camps & ELK Ski
Outdoor dining
Forest Hideout Cottage • Nature Haven Close to Ski Adventures

Forest Hideout Cottage • Nature Haven Close to Ski Adventures

Forest Hideout Cottage • Nature Haven Close to Ski Adventures
2.0 star property
Pleasant Mount
$259 nightly
The price is $279
Dec 22 - Dec 23
Total with taxes and fees
Forest Hideout Cottage • Nature Haven Close to Ski Adventures
Exterior
City Escape • Close to Camps & ELK Ski

City Escape • Close to Camps & ELK Ski

City Escape • Close to Camps & ELK Ski
2.0 star property
Pleasant Mount
$485 nightly
The price is $525
Dec 22 - Dec 23
Total with taxes and fees
City Escape • Close to Camps & ELK Ski
Outdoor dining
Cottage and Suite • Perfect Stay Close to Ski Slopes

Cottage and Suite • Perfect Stay Close to Ski Slopes

Cottage and Suite • Perfect Stay Close to Ski Slopes
2.0 star property
Pleasant Mount
$478 nightly
The price is $518
Dec 22 - Dec 23
Total with taxes and fees
Cottage and Suite • Perfect Stay Close to Ski Slopes
Exterior
Woodland Hideout • Romantic Escape Close to Ski Trails

Woodland Hideout • Romantic Escape Close to Ski Trails

Woodland Hideout • Romantic Escape Close to Ski Trails
2.0 star property
Pleasant Mount
$474 nightly
The price is $513
Dec 22 - Dec 23
Total with taxes and fees
Woodland Hideout • Romantic Escape Close to Ski Trails
Exterior
Countryside Retreat Near Ski Slopes

Countryside Retreat Near Ski Slopes

Countryside Retreat Near Ski Slopes
2.0 star property
Pleasant Mount
$478 nightly
The price is $518
Dec 22 - Dec 23
Total with taxes and fees
Countryside Retreat Near Ski Slopes
Outdoor dining
Family Cottage Escape • Group‑Friendly Retreat Close to Skiing

Family Cottage Escape • Group‑Friendly Retreat Close to Skiing

Family Cottage Escape • Group‑Friendly Retreat Close to Skiing
2.0 star property
Pleasant Mount
$489 nightly
The price is $529
Dec 22 - Dec 23
Total with taxes and fees
Family Cottage Escape • Group‑Friendly Retreat Close to Skiing
Exterior
Country Escape • Near Camps & Ski

Country Escape • Near Camps & Ski

Country Escape • Near Camps & Ski
2.0 star property
Pleasant Mount
$514 nightly
The price is $556
Dec 22 - Dec 23
Total with taxes and fees
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

Family Cottage and Suite • Country Cottage Close to Ski Mountain
2.0 star property
Pleasant Mount
$514 nightly
The price is $556
Dec 22 - Dec 23
Total with taxes and fees
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

Premier Cottages & Suite • Cozy Cottage Near Ski Mountain
2.0 star property
Pleasant Mount
$752 nightly
The price is $815
Dec 22 - Dec 23
Total with taxes and fees
Premier Cottages & Suite • Cozy Cottage Near Ski Mountain
Exterior
Premium Cottages and Suites • Near Camps • Autumn Midweek - 35% OFF Promo!

Premium Cottages and Suites • Near Camps • Autumn Midweek - 35% OFF Promo!

Premium Cottages and Suites • Near Camps • Autumn Midweek - 35% OFF Promo!
2.0 star property
Pleasant Mount
$1,165 nightly
The price is $1,261
Dec 22 - Dec 23
Total with taxes and fees
Premium Cottages and Suites • Near Camps • Autumn Midweek - 35% OFF Promo!
Exterior
Bring the Kids • Family Getaway Near Ski Trails

Bring the Kids • Family Getaway Near Ski Trails

Bring the Kids • Family Getaway Near Ski Trails
2.0 star property
Pleasant Mount
$1,043 nightly
The price is $1,129
Dec 22 - Dec 23
Total with taxes and fees
Bring the Kids • Family Getaway Near Ski Trails
Exterior
Family Cottage and Suite • Mountain Retreat Near Ski Slopes

Family Cottage and Suite • Mountain Retreat Near Ski Slopes

Family Cottage and Suite • Mountain Retreat Near Ski Slopes
2.0 star property
Pleasant Mount
$893 nightly
The price is $967
Dec 22 - Dec 23
Total with taxes and fees
Family Cottage and Suite • Mountain Retreat Near Ski Slopes
Exterior
Premium Cottages and Suites • Mountain Retreat Near Ski Slopes

Premium Cottages and Suites • Mountain Retreat Near Ski Slopes

Premium Cottages and Suites • Mountain Retreat Near Ski Slopes
2.0 star property
Pleasant Mount
$879 nightly
The price is $952
Dec 22 - Dec 23
Total with taxes and fees
Premium Cottages and Suites • Mountain Retreat Near Ski Slopes
Exterior
Family Suites •Close to Ski Runs Near Elk Mountain Ski Slopes

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

Family Suites •Close to Ski Runs Near Elk Mountain Ski Slopes
2.0 star property
Pleasant Mount
$801 nightly
The price is $867
Dec 22 - Dec 23
Total with taxes and fees
Family Suites •Close to Ski Runs Near Elk Mountain Ski Slopes
Exterior
2BR Premium Duplex • Close to Ski Adventures

2BR Premium Duplex • Close to Ski Adventures

2BR Premium Duplex • Close to Ski Adventures
Pleasant Mount
9.0 out of 10, Wonderful, (2)
"Would've liked to have more to cook with than just a microwave, other than that the stay was commendable."
United States
Jeremy
$343 nightly
The price is $371
Dec 22 - Dec 23
Total with taxes and fees
2BR Premium Duplex • Close to Ski Adventures
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

Red Roof Inn Binghamton - Johnson City

Red Roof Inn Binghamton - Johnson City

10/10 Excellent
"Staff was great. Room was obviously recently renovated. Comfy furniture. Best heat in a hotel room in a VERY long time! We will stay again when in the area."
Cynthia C. 1-night trip
Posted 2 days ago
Red Roof Inn Binghamton - Johnson City

Find out more about Windsor

Windsor Cottages information

Number of reviews
25
Accommodation
79 Cottages
Lowest Price
$229
Highest Price
$1,261

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