Photo by Jennifer Hill

Windsor Vacation Rentals

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

Tonight
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 26 - Sep 28
Next weekend
Oct 3 - Oct 5

Vacation Rentals in Windsor

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, (342)
"We enjoyed our stay at this well equipped and designed cottage. We loved the decks and location on the river. "
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
7 Bedroom Oceanfront in Dillon Beach with spa
Dining

7 Bedroom Oceanfront in Dillon Beach with spa

9.4 out of 10, Exceptional, (162)
"We have a group of four families that stay here once a year. It's always a pleasure, and every time we stay we see a few more things are improved from the last time we were there... which is always nice to see."
7 Bedroom Oceanfront in Dillon Beach with spa
Oceanfront - Hot Tub - Newly Remodeled Cottage
Outdoor spa tub

Oceanfront - Hot Tub - Newly Remodeled Cottage

9.8 out of 10, Exceptional, (393)
"This property is in a great location located on the ocean in bodega Bay. Great ocean views, gardens, very clean property 12 minutes from restaurants hiking trails everywhere. We had a wonderful stay."
Oceanfront - Hot Tub - Newly Remodeled Cottage
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
Interior

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

9.8 out of 10, Exceptional, (455)
"It was great as always"
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
The Ranch at Lake Sonoma
Front of property

The Ranch at Lake Sonoma

1.0 star property
10.0 out of 10, Exceptional, (1)
"The location is fantastic, with a spectacular view on the lake if you choose a lakeview. A very genuine welcome from The Ranch team, with all detailed explanations, a map to help you to navigate around. For our first time going camping, we want definitely to come back there !"
The price is ￥8,768
￥9,996 total
includes taxes & fees
Sep 25 - Sep 26
The Ranch at Lake Sonoma
COZY—Dog-Friendly—Perfect for Couples!!! 2025 DISCOUNT for 5-10 days—ASK!!!
Beach

COZY—Dog-Friendly—Perfect for Couples!!! 2025 DISCOUNT for 5-10 days—ASK!!!

9.6 out of 10, Exceptional, (186)
"Perfect get away for my wifes 60th."
COZY—Dog-Friendly—Perfect for Couples!!! 2025 DISCOUNT for 5-10 days—ASK!!!
Bright Home 800 Feet from Salmon Creek Beach w/ Wood Stove & Pool Table
Dining

Bright Home 800 Feet from Salmon Creek Beach w/ Wood Stove & Pool Table

8.2 out of 10, Very Good, (46)
"Walking distance to the beach and a warm and inviting space to return to. Perfect for our weekend getaway."
Bright Home 800 Feet from Salmon Creek Beach w/ Wood Stove & Pool Table
Ocean Front/3 minute walk/Hotub/Sauna/Pets/Massage Chair/Pinball/Pac-Man Machine
On the beach, sun loungers

Ocean Front/3 minute walk/Hotub/Sauna/Pets/Massage Chair/Pinball/Pac-Man Machine

9.0 out of 10, Wonderful, (304)
"Ideal spot next to Dillon beach, which is dog friendly and close to so many other points of interest! We had a lovely time relaxing here and listening to the surf."
Ocean Front/3 minute walk/Hotub/Sauna/Pets/Massage Chair/Pinball/Pac-Man Machine
Charming Bayfront Cottage with Gorgeous Views - Ideal for Quick Romantic Getaway
Beach nearby

Charming Bayfront Cottage with Gorgeous Views - Ideal for Quick Romantic Getaway

9.0 out of 10, Wonderful, (94)
"Beautiful view, litterally on tge water."
Charming Bayfront Cottage with Gorgeous Views - Ideal for Quick Romantic Getaway
Wine Country Getaway With Pool, Hot Tub, Garden, Views, Location!
Outdoor pool

Wine Country Getaway With Pool, Hot Tub, Garden, Views, Location!

9.8 out of 10, Exceptional, (132)
"We had an incredible stay at this lovely home in Glen Ellyn! The house easily and comfortably sleeps up to 12. Very clean with a beautiful kitchen. The grounds are incredible. The pool is delightful and so is the rock waterslide. We loved dining on the Tuscan inspired outdoor table each evening and listened to music around the pit fire afterward. The gardens are so pretty. Our host was just lovely to work with! We will be back next year."
Wine Country Getaway With Pool, Hot Tub, Garden, Views, Location!
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Interior

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

10.0 out of 10, Exceptional, (242)
"Loved the house and location! "
The price is ￥273,079
￥352,862 total
includes taxes & fees
Sep 25 - Sep 26
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!
Interior

Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!

9.4 out of 10, Exceptional, (346)
"The property was beautiful and perfect! We absolutely loved our stay here, and are looking forward to coming back again."
The price is ￥37,518
￥81,488 total
includes taxes & fees
Sep 29 - Sep 30
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!
Escape to Wine County in your independant Cottage in Downtown Calistoga
Terrace/patio

Escape to Wine County in your independant Cottage in Downtown Calistoga

9.6 out of 10, Exceptional, (25)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is ￥44,135
￥60,245 total
includes taxes & fees
Sep 29 - Sep 30
Escape to Wine County in your independant Cottage in Downtown Calistoga
Casa Bella Estate in Wine Country w/ New Pool!
Outdoor dining

Casa Bella Estate in Wine Country w/ New Pool!

9.6 out of 10, Exceptional, (131)
"Cozy Location for a Corporate retreat!"
Casa Bella Estate in Wine Country w/ New Pool!
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, (281)
"Lovely house, setting and host!"
Romantic, Dramatic Views! Full calendar https://www.vrbo.com/81742?dateless=true
Gorgeously styled bungalow overlooking Bodega Harbor, Sauna, walk to town, Dogs
Fridge, oven, stovetop, dishwasher

Gorgeously styled bungalow overlooking Bodega Harbor, Sauna, walk to town, Dogs

9.8 out of 10, Exceptional, (97)
"Perfect yard for our tiny dogs. We even had 2 foxes visit up on the roof. Perfect location to walk to stores and quick drives to hikes."
Gorgeously styled bungalow overlooking Bodega Harbor, Sauna, walk to town, Dogs
Luxe Surf Shack | Rooftop Hot Tub, Games + Near Beach
Terrace/patio

Luxe Surf Shack | Rooftop Hot Tub, Games + Near Beach

10.0 out of 10, Exceptional, (21)
"The house was fantastic and in a great location. We'd definitely stay here again on future trips."
Luxe Surf Shack | Rooftop Hot Tub, Games + Near Beach
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Outdoor dining

Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

10.0 out of 10, Exceptional, (237)
"Truly one of the best rentals I’ve ever stayed in. The host is super responsive and easy to work with, the house is great and the views/outdoor space are absolutely incredible. Would love to return in the future! "
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
Fridge, microwave, oven, stovetop

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

10.0 out of 10, Exceptional, (65)
"Smooth check-in process. Close to plenty of vineyards. Very friendly staff. "
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
Luxurious Large Home, Beautiful Pool, Extensive Gardens
Beach towels

Luxurious Large Home, Beautiful Pool, Extensive Gardens

9.8 out of 10, Exceptional, (155)
"We had a great time hanging out at the pool with the family,"
Luxurious Large Home, Beautiful Pool, Extensive Gardens
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

Hotel Centro Sonoma Wine Country, Tapestry Collection Hilton

Hotel Centro Sonoma Wine Country, Tapestry Collection Hilton

10/10 Excellent
"Wish they had breakfast"
Heather L 1-night trip
Posted 3 days ago
Hotel Centro Sonoma Wine Country, Tapestry Collection Hilton

Find out more about Windsor

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, we have vacation rentals in Windsor near Dom Whitney Tasting Lounge, or you can go with a secluded option if you're looking for a relaxing stay. Our travelers say Windsor has a good selection of top-notch restaurants and wineries. Make sure you have time to check out the festivals while you're in the area.

What's the top vacation rental that Windsor has to offer?

7 Bedroom Oceanfront in Dillon Beach with spa: Visitors like this Windsor vacation home rental. It is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

How many vacation rentals are there in Windsor?

Choose from 34 Expedia vacation rentals in Windsor for a memorable vacation.

What can I see and do in Windsor?

Family-friendly attractions include Dom Whitney Tasting Lounge and Powell's Sweet Shoppe - Windsor, whereas Russian River is a spot to enjoy the outdoors. Windsor Golf Club and Pacific Coast Air Museum are other places to visit while you're in town.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Windsor. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a small group gathering.