Photo by Jennifer Hill

Search Cottages in Windsor

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Cottages in Windsor

Panoramic Ocean View--3 Min Walk To Beach
Dining

Panoramic Ocean View--3 Min Walk To Beach

9.6 out of 10, Exceptional, (312)
"Great place to stay. Perfect walk to the beach and very relaxing. Loved the view from the deck. Great kitchen, clean house and comfortable bed. "
Panoramic Ocean View--3 Min Walk To Beach
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
Terrace/patio

Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

9.8 out of 10, Exceptional, (329)
"We enjoyed our stay! So much to see and do in the RR valley! "
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
Oceanfront - Hot Tub - Newly Remodeled Cottage
Outdoor spa tub

Oceanfront - Hot Tub - Newly Remodeled Cottage

9.8 out of 10, Exceptional, (383)
"Our third stay and first time booking three nights which seems to be the sweet spot for an extended weekend since you get two full days to relax along the coast. Already can't wait to book our next visit to this charming property!"
Oceanfront - Hot Tub - Newly Remodeled Cottage
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (41)
"We rented this place for our babymoon and it met all of our expectations! The host is very friendly and prompt. The place was clean and had all necessities. It’s a short walk to the beach which was perfect for our pup! Hopefully we have the chance to stay here again!"
The price is AED 1,372
AED 2,583 total
includes taxes & fees
23 Jul - 24 Jul
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Escape to Wine County in your independant Cottage in Downtown Calistoga
Terrace/patio

Escape to Wine County in your independant Cottage in Downtown Calistoga

9.8 out of 10, Exceptional, (20)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is AED 1,098
AED 1,499 total
includes taxes & fees
16 Jul - 17 Jul
Escape to Wine County in your independant Cottage in Downtown Calistoga
Enjoy Fresh Ocean Breezes, No Crowds In Small Community Setting
Interior

Enjoy Fresh Ocean Breezes, No Crowds In Small Community Setting

10.0 out of 10, Exceptional, (370)
"A wonderful cozy house."
Enjoy Fresh Ocean Breezes, No Crowds In Small Community Setting
Backyard Garden Oasis
Property grounds

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (47)
"perfect place"
The price is AED 713
AED 795 total
includes taxes & fees
16 Jul - 17 Jul
Backyard Garden Oasis
Comfort and Style in Our Queen Cottage
Dining

Comfort and Style in Our Queen Cottage

9.8 out of 10, Exceptional, (48)
"Nice location and space was very comfortable"
The price is AED 657
AED 888 total
includes taxes & fees
17 Jul - 18 Jul
Comfort and Style in Our Queen Cottage
Romantic, Dramatic Views! Full calendar https://www.vrbo.com/81742?dateless=true
Smart TV, fireplace, books, music library

Romantic, Dramatic Views! Full calendar https://www.vrbo.com/81742?dateless=true

10.0 out of 10, Exceptional, (270)
"Great place to stay. Excellent host"
Romantic, Dramatic Views! Full calendar https://www.vrbo.com/81742?dateless=true
Studio cottage retreat in a vineyard setting
Outdoor dining

Studio cottage retreat in a vineyard setting

10.0 out of 10, Exceptional, (63)
"Great little place - highly recommend!"
Studio cottage retreat in a vineyard setting
TREE HOUSE, WITH INDOOR/OUTDOOR SHOWER, PRIVATE DECK, POOL & INFIINITY HOT TUB
Exterior

TREE HOUSE, WITH INDOOR/OUTDOOR SHOWER, PRIVATE DECK, POOL & INFIINITY HOT TUB

TREE HOUSE, WITH INDOOR/OUTDOOR SHOWER, PRIVATE DECK, POOL & INFIINITY HOT TUB
Wine Country Bungalow
Fridge, microwave, oven, stovetop

Wine Country Bungalow

9.8 out of 10, Exceptional, (44)
"Very comfortable and super clean"
Wine Country Bungalow
Chalk Hill Cottage Close to Wineries
Exterior

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (37)
"The Chalk Hill cottage was the perfect getaway for Sonoma wine lovers. Located in Alexander Valley and close to great wineries."
Chalk Hill Cottage Close to Wineries
Sweet, dog-friendly cottage in the redwoods with river beach access & fireplace
Terrace/patio

Sweet, dog-friendly cottage in the redwoods with river beach access & fireplace

9.2 out of 10, Wonderful, (14)
"A very cozy and clean home. Perfect for our girls getaway and fur babies."
Sweet, dog-friendly cottage in the redwoods with river beach access & fireplace
Private 1-bedroom Guest House with Great Amenities
Terrace/patio

Private 1-bedroom Guest House with Great Amenities

10.0 out of 10, Exceptional, (11)
"Our group had a wonderful time. The property was perfect in every way & would certainly rent again if lucky enough to return to Healdsburg."
Private 1-bedroom Guest House with Great Amenities
Brand new modern cottage in the heart of Glen Ellen on Sonoma Creek.
Interior

Brand new modern cottage in the heart of Glen Ellen on Sonoma Creek.

10.0 out of 10, Exceptional, (5)
Brand new modern cottage in the heart of Glen Ellen on Sonoma Creek.
1 Bedroom Cottage Walking Distance to Down Town
Fridge, microwave, oven, stovetop

1 Bedroom Cottage Walking Distance to Down Town

10.0 out of 10, Exceptional, (54)
"Great spot for the dogs!"
1 Bedroom Cottage Walking Distance to Down Town
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
Property grounds

Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown

9.8 out of 10, Exceptional, (42)
"We had a perfect experience. The house is very clean and functional and the location simply cannot be beat. The local management company was very responsive and helpful. We stayed for 2 weeks and really got a feel for living in town given the proximity to restaurants, coffee shops, highways, wineries etc. I would highly recommend this house and we will absolutely be back if they will have us."
The price is AED 1,998
AED 4,059 total
includes taxes & fees
29 Jul - 30 Jul
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
Redwoods Cabin w/ Hot Tub: Walk to Russian River!
Interior

Redwoods Cabin w/ Hot Tub: Walk to Russian River!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Home is a very relaxing and comfortable and kitchen is well stocked for those who enjoy cooking. Lovely deck in front with a hottub that works well. Plenty of towels for both bathrooms. Nice welcoming decor and a great place surrounded by redwoods. "
Redwoods Cabin w/ Hot Tub: Walk to Russian River!
Beautiful, Historic Guest Ranch with Modern Amenities
Outdoor pool

Beautiful, Historic Guest Ranch with Modern Amenities

10.0 out of 10, Exceptional, (84)
"We absolutely loved our time there! "
Beautiful, Historic Guest Ranch with Modern Amenities
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
Sign in
Sign up, it's free

Frequently asked questions

How much do cottages in Windsor cost?
Rates for cottages in Windsor range between AED 657 and AED 1,998 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 139 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.
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!