A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.

Search Windsor Cottage Rentals from CA $282

  • 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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Windsor cottages

A two-story house with a front porch, a mailbox, and a number 839 on the front wall.

1. Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (82 reviews)
"Our stay was pleasant, the place was exceptionally clean and the owners were very helpful."
United States
joanne h.
The price is CA $299
CA $609 total
includes taxes & fees
Nov 27 - Nov 28
Wine Country Cottage in downtown Santa Rosa, CA
yard view of old growth stump, stairs to front door, gate from off-parking

2. Pumpkin House Summary

Pumpkin House Summary
Guerneville
10.0 out of 10, Exceptional, (13 reviews)
"Nice place, quiet. Loved the hot tub. "
United States
Nathan B.
The price is CA $259
CA $524 total
includes taxes & fees
Oct 28 - Oct 29
Pumpkin House Summary
A modern building with a metal exterior, a wooden door, and a small window on the side.

3. Country Carriage House in Downtown Geyserville, Vineyard Views

Country Carriage House in Downtown Geyserville, Vineyard Views
Geyserville
10.0 out of 10, Exceptional, (5 reviews)
"Cozy, rustic, and with all great amenities."
United States
Gina I.
The price is CA $228
CA $547 total
includes taxes & fees
Oct 29 - Oct 30
Country Carriage House in Downtown Geyserville, Vineyard Views
A wooden deck with wicker furniture and a metal table, overlooking a vineyard and hills.

4. Garden house with gas fireplace

Garden house with gas fireplace
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"It was a quaint country house. The host was attentive, but also left us to ourselves. The house was clean. A/C worked well. It was very comfortable."
United States
Amy
The price is CA $137
CA $282 total
includes taxes & fees
Oct 29 - Oct 30
Garden house with gas fireplace
A small, single-story house with a front porch, a chimney, and a door with a window above it.

5. Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.6 out of 10, Exceptional, (49 reviews)
"We stayed here 15 years ago , same bedspreads and no new updates . We love it for its cozy feeling , and love the peacefulness of staying in Calistoga. We walked across the street for an awesome dinner at Sam’s Social club , walked down the street to shop and cruise around this quaint town . It’s a high price point , but we always enjoy our time there . I worry that if they ever remodel this place , the price point will be more than what it’s worth a night , for which I don’t believe would be...
United States
William
The price is CA $461
CA $632 total
includes taxes & fees
Oct 28 - Oct 29
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
A small, single-story house with a front porch, a chimney, and a door with a window above it.

6. Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Calistoga
10.0 out of 10, Exceptional, (5 reviews)
"Property is beautiful rooms are so clean. Service was incredible."
United States
Paul L.
The price is CA $419
CA $574 total
includes taxes & fees
Oct 28 - Oct 29
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
A wooden pathway leading to a treehouse with a wooden deck and a staircase.

7. Hillside Retreat in the Redwoods | Hot Tub

Hillside Retreat in the Redwoods | Hot Tub
Guerneville
10.0 out of 10, Exceptional, (5 reviews)
"Great place! Nice and cozy!"
United States
John B.
The price is CA $507
CA $902 total
includes taxes & fees
Nov 12 - Nov 13
Hillside Retreat in the Redwoods | Hot Tub
A laptop on a wooden table with a smartphone and a cup.

8. Escape to wine country in your independent cottage in downtown Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
9.8 out of 10, Exceptional, (8 reviews)
"We absolutely loved our stay! The home was clean, quiet, private, and incredibly convenient. We were especially grateful that the hosts allowed our three dogs, which made this trip extra special. We spent a few days enjoying Calistoga and Napa before taking our sweet pup to UC Davis, and this was the perfect place for us. As empty nesters, we love traveling with our three dogs and hope to stay here again someday!"
United States
Jennifer G.
The price is CA $419
CA $574 total
includes taxes & fees
Oct 28 - Oct 29
Escape to wine country in your independent cottage in downtown Calistoga
A wooden deck with a stone pathway leading to a hammock.

9. Stunning Sauna Cottage Retreat on Private Vineyard

Stunning Sauna Cottage Retreat on Private Vineyard
Sebastopol
10.0 out of 10, Exceptional, (3 reviews)
"Nice area in the vineyards. Sauna was great. Place was clean. "
United States
Cesar R.
The price is CA $391
CA $676 total
includes taxes & fees
Nov 1 - Nov 2
Stunning Sauna Cottage Retreat on Private Vineyard
A two-story house with a wooden deck and a covered front porch.

10. Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog

Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Dillon Beach
10.0 out of 10, Exceptional, (85 reviews)
"Lovely spot for a getaway!"
United States
Lisa M.
The price is CA $377
CA $789 total
includes taxes & fees
Oct 29 - Oct 30
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
A deck with a sofa, a glass-top coffee table, and a view of a hilly landscape.

11. Dog-friendly Haven w/ Stunning Views in Bodega Bay

Dog-friendly Haven w/ Stunning Views in Bodega Bay
3.0 star property
Bodega Bay
The price is CA $588
CA $1,354 total
includes taxes & fees
Nov 5 - Nov 6
Dog-friendly Haven w/ Stunning Views in Bodega Bay
A wooden deck with a red umbrella, a wooden chair, and a table.

12. Relaxing Beekeeper's Cottage with hot tub

Relaxing Beekeeper's Cottage with hot tub
Bodega Bay
10.0 out of 10, Exceptional, (22 reviews)
"The cottage was charming, clean and well appointed. "
United States
Edie H.
The price is CA $447
CA $880 total
includes taxes & fees
Nov 16 - Nov 17
Relaxing Beekeeper's Cottage with hot tub
A two-story house with a covered porch, a stone pathway, and a well-maintained garden with various shrubs and trees.

13. The Atlas Calistoga - Cottage #3

The Atlas Calistoga - Cottage #3
Calistoga
10.0 out of 10, Exceptional, (22 reviews)
"Great cottage within walking distance to downtown Calistoga."
United States
Joel S.
The price is CA $655
CA $1,013 total
includes taxes & fees
Oct 31 - Nov 1
The Atlas Calistoga - Cottage #3
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

Quality Inn Petaluma - Sonoma

Quality Inn Petaluma - Sonoma

10/10 Excellent
"Excellent great staff"
Peter 1-night trip
Posted 1 hour ago
Quality Inn Petaluma - Sonoma

Find out more about Windsor

Windsor Cottages information

Number of reviews
296
Accommodation
127 Cottages
Lowest Price
CA $282
Highest Price
CA $1,354

Frequently asked questions

How much do cottages in Windsor cost?
Rates for cottages in Windsor range between CA $282 and CA $1,354 per night. No matter your budget, you'll find the perfect place to reconnect with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Windsor?
Pack your bags and pick from 127 cottages in Windsor. Thinking about a place where you can relax and connect with nature? Expedia can help you find your ideal stay in a few simple clicks.
Are there any family-friendly cottages in Windsor?
Put your bags down at Wine Country Getaway Modern Three and make your family getaway to Windsor nice and comfortable. This family-friendly cottage has a 3-star rating and conveniences such as an oven and WiFi. Once you've checked in and dropped off your bags, there are loads of family-friendly attractions to explore in and around Windsor. Safari West and Rubicon Adventures guarantee a good time for young and old.
Why book your cottage in Windsor with Expedia?
Reserving a cottage in Windsor is as simple as deciding on your travel dates and picking an ideal place for outdoor relaxation and recreation. From ritzy retreats to affordable properties and cottages that come with amenities like laundry facilities, Expedia has something for all traveler tastes. As for the best offers around? We've got them too!
How can I find cheap cottages in Windsor?
The best way to compare cheap cottages in Windsor is with Expedia's filter tool. Refine your search by star rating, amenities and budget to nab unbeatable prices in just a few keystrokes.
What is there to do in Windsor near my cottage?
Windsor has enough activities and experiences to keep you going for weeks, beginning with Pacific Coast Air Museum. Windsor Golf Club, Sonoma-Cutrer Vineyards Cutrer Vineyard and Russian Hill Estate Vineyards are other awesome attractions. If you're hanging around a while, Windsor Oaks Vineyards and Powell's Sweet Shoppe - Windsor are nice finishing touches to your itinerary.

Explore a world of travel with Expedia