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Compare 111 Cottages in Windsor with updated reviews, rates, and availability.

Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
9.8 out of 10, Exceptional, (291)
"This was a marvelous cottage in a beautiful and quiet location between the ocean and Guerneville. There were even restaurants just down the road. The place was clean, comfortable, attractive, and well supplied. The space was roomy and bright. We didn't use the wonderful deck much because of the weather, but we enjoyed the hot tub looking up at the redwoods. We would highly recommend this property and would happily return!"
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
Oceanfront - Hot Tub - Newly Remodeled Cottage
9.8 out of 10, Exceptional, (349)
"Very nice. "
Oceanfront - Hot Tub - Newly Remodeled Cottage
Romantic, Dramatic Views! Full calendar https://www.vrbo.com/81742?dateless=true
10.0 out of 10, Exceptional, (236)
"Loved, loved, loved this VRBO. We loved the charm of this home. The cleanliness, the views, the town of Dillon Beach. One of our best getaways we had in a long time. We will be back. Thanks for the opening your beautiful home to us."
Romantic, Dramatic Views! Full calendar https://www.vrbo.com/81742?dateless=true
Escape to Wine County in your independant Cottage in Downtown Calistoga
9.8 out of 10, Exceptional, (9)
"We stayed here for two nights. It was unseasonably hot so we spent more time in our room than usual and it was so comfortable, loved the filtered water, no complaints. Breakfast was ok - allowed us to get started for the day. It was our first trip to Napa valley and so glad we stayed in Calistoga - small, quiet and quaint. Nice contrast to the town of Napa. "
The price is AED 1,010
AED 1,365 total
includes taxes & fees
18 Nov - 19 Nov
Escape to Wine County in your independant Cottage in Downtown Calistoga
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
9.8 out of 10, Exceptional, (34)
"What a perfect spot from which to explore Healdsburg! The location couldn't be better for walking to everything downtown, and also to the Seghesio winery. The home is beautiful, well decorated, and stocked with everything you need in the kitchen. Good attention to detail. We thoroughly enjoyed our stay. "
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
Creekside Cottage and Bungalow. Cozy, pet friendly, close to town. Sleeps 6
10.0 out of 10, Exceptional, (6)
"This house has everything you need. Very well stocked. Amazing property, especially the yard. 5min to town, very convenient location. Will be back for sure "
Creekside Cottage and Bungalow. Cozy, pet friendly, close to town. Sleeps 6
Enjoy Fresh Ocean Breezes, No Crowds In Small Community Setting
10.0 out of 10, Exceptional, (357)
"A cozy cottage close to public beach access. Pam was a joy to communicate with and very accommodating to our last minute request. She went above and beyond informing us of all necessary details. I recommend her home!"
Enjoy Fresh Ocean Breezes, No Crowds In Small Community Setting
Healdsburg Cottage Walk to the Plaza, Workspace
9.8 out of 10, Exceptional, (219)
"Just an adorable space and so well appointed! Kelly was easy to communicate with and the check in process was cake! We could walk to the Healdsburg plaza and it’s a quick drive to tons of wineries. We will definitely be visiting again!"
Healdsburg Cottage Walk to the Plaza, Workspace
Raymond Bakery - Elim Grove Cottage B&B - Bed and Breakfast
9.6 out of 10, Exceptional, (84)
"Wonderful Fri Eve pizza & music night. Loved hearing the orchestra band camp throughout the days as well. Loved that turn table & records were provided. However "
Raymond Bakery - Elim Grove Cottage B&B - Bed and Breakfast
TREE HOUSE, WITH INDOOR/OUTDOOR SHOWER, PRIVATE DECK, POOL & INFIINITY HOT TUB
TREE HOUSE, WITH INDOOR/OUTDOOR SHOWER, PRIVATE DECK, POOL & INFIINITY HOT TUB
Chalk Hill Cottage Close to Wineries
9.8 out of 10, Exceptional, (25)
"The cottage is very nice and well appointed, with all the needed amenities and more! Very convenient location to visit local wineries and the town of Healdsburg. It was very easy to communicate with our hosts as well. We had a great stay!"
Chalk Hill Cottage Close to Wineries
Sunny View Cottage in the Beautiful Wine Country
10.0 out of 10, Exceptional, (259)
"Beautiful property inside and out, friendly and helpful hosts, perfect location for me - close to Santa Rosa, easy drive to Armstrong Woods, near the friends and relatives I was visiting! I hope to be back!"
Sunny View Cottage in the Beautiful Wine Country
Wine Country Bungalow
10.0 out of 10, Exceptional, (34)
"We were thankful to find an affordable place in Wine Country that didn't break the bank. The beds were comfortable, lots of towels, clean bathroom with working toilets (yayI). There was a nice backyard with a BBQ that we didn't use. Note this house is smaller than it looks in the photos. The kitchen was small, but is was fine, we didn't cook while there. Basic kitchen for a short stay. This house rules insists on quite hours. Late night parties are forbidden. Which were pretty...
Wine Country Bungalow
Beautiful, Historic Guest Ranch with Modern Amenities
10.0 out of 10, Exceptional, (83)
"We had such a wonderful 4 days in this beautiful home and environs. After a very stressful few months for all in my family, this was the perfect place to rejuvenate and leave restored. Every need we had was quickly addressed by the owner and her staff. We cannot wait to return next fall."
Beautiful, Historic Guest Ranch with Modern Amenities
Backyard Garden Oasis
3.0 star property
9.6 out of 10, Exceptional, (42)
"The Backyard Garden Oasis was quiet and secluded. We enjoyed walking along the quiet street in the morning. The owner is a helpful host. "
The price is AED 707
AED 789 total
includes taxes & fees
6 Nov - 7 Nov
Backyard Garden Oasis
1 Bedroom Cottage Walking Distance to Down Town
10.0 out of 10, Exceptional, (47)
"Property was quiet and cute. The bed was very comfortable and the linens were wonderful. "
1 Bedroom Cottage Walking Distance to Down Town
Vineyard View Home with a Complimentary Wine Tasting
9.0 out of 10, Wonderful, (6)
"The house itself was very nice and the owner was very communicative for the most part. Outside of that, we unfortunately had a very negative experience as the location of the house was over 2.5 miles from town (Where the listing had shown it to be) which resulted in us being stranded in town on the final night of our stay. This difference was material, and the location was the sole reason we booked it as we anticipated transportation being difficult and had a busy weekend of wedding events...
Vineyard View Home with a Complimentary Wine Tasting
Heron House--The River House in the Redwoods
9.8 out of 10, Exceptional, (20)
"We really enjoyed the home and property and having the intertubes to float on was really nice. I was a bit confused by the listing which showed 3 bedrooms but then listed a sofa bed as a "4th" bedroom in the listing. We arrived believing the 4th bedroom would provide some privacy but that was my error. We also weren't able to use the barbeque due to a propane leak at the tank but we made due with the beautiful stove and everything turned out great. I especially loved the gated driveway which...
Heron House--The River House in the Redwoods
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
10.0 out of 10, Exceptional, (29)
"Sundog and the host, Valerie, were both absolutely amazing. Sundog was more than we could have asked for and had everything we needed. Nice short walk to the beach, comfy beds, fenced backyard for our furry children and a fully stocked kitchen including local yummies. Valerie was the best host we have every experienced, kind, helpful and goes above and beyond to make sure you have a wonderful time. This is a must home for a relaxing, lovely getaway. WE WILL BE BACK!!! Thank you Valerie for...
The price is AED 2,112
AED 3,533 total
includes taxes & fees
26 Nov - 27 Nov
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Private 1-bedroom Guest House with Great Amenities
10.0 out of 10, Exceptional, (11)
"We just stayed at this magnificent property for a week and it was pure bliss. I can't overstate what a special place this is. Fredric and his wonderful wife were amazing hosts. They could not have been more thoughtful, or generous! The property is in a really beautiful location. It offered the perfect mix of peace and quiet, whilst still being just a short distance from all the many fabulous amenities the area has to offer. We loved the outdoor patio and the beautiful gardens! We had such a...
Private 1-bedroom Guest House with Great 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.
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Other property types in Windsor

Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, (91)
"The property was very good and met all our needs with a couple of exceptions. The bathroom towels were not good, a little smelly and really need to be upgraded along with the toilet paper!"
Cottage home near the Russian River; county parks; numerous wineries
Casa de la Esperanza: 1890s Historic Gem - 6BD/4BA
9.8 out of 10, Exceptional, (6)
"The property views in pictures as higher end than it truly is and I think is overpriced. The floors and kitchen cabinets are uneven. The back house is not level. The bathrooms are nicely done and the space/beds are perfect for a large group. The upstairs area was perfect for our family who had toddlers as they all stayed together in the large room. The owner sent what must have been automated communications during our stay as they offered to bring additional consumables but when I replied...
Casa de la Esperanza: 1890s Historic Gem - 6BD/4BA
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
10.0 out of 10, Exceptional, (217)
"We all enjoyed the stay. The property was very clean and welcoming. Beds were all comfortable and the kitchen was stocked with all needs. "
The price is AED 6,060
AED 7,706 total
includes taxes & fees
10 Nov - 11 Nov
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
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.

Frequently asked questions

How much do cottages in Windsor cost?
Prices for cottages in Windsor range between AED 707 and AED 2,112 per night. No matter your budget, you’ll find the perfect place to relax and 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?
Get in touch with nature in one of the 111 cottages on offer in Windsor. To help you choose your ideal stay, make use of our handy filters to search for amenities or perks you prefer.
Why book your cottage in Windsor with Expedia?
Expedia has some great cottages in Windsor, so get ready for an unforgettable stay on nature’s doorstep. If you have a set budget, click on how much you want to spend and your preferred property star rating. Or, make the most of our filters to search for cottages with a hot tub or free WiFi. We’ll help you find the perfect fit whatever your plans or style of travel.
How can I find cheap cottages in Windsor?
With Expedia’s helpful filter tool, comparing cheap cottages in Windsor is a breeze. To find stays that are very pocket friendly, refine your search results by amenities, budget and star rating.