Photo by Jennifer Hill

Holiday Homes in Windsor

Most properties are fully refundable. Because flexibility matters.

Save an average of 15% on thousands of hotels with Expedia Rewards

Search over 2.9 million properties and 550 airlines worldwide

Find properties with these dates

Featured Holiday Homes in Windsor and around

Living area
New Modern House in Sonoma Valley's Best Area
10.0 out of 10, Exceptional, (202)
"We loved our stay. The cottage is perfection! Nicely appointed. Great outdoor living space. Perfect setting. Close to town but so peaceful and serene!"
New Modern House in Sonoma Valley's Best Area
Fridge, microwave, oven, stovetop
Dog-friendly home with firepit, Hot tub, woodstove & 2 decks - walk to beach
9.6 out of 10, Exceptional, (10)
"The house was well placed, near Guerneville, restaurants and activities. Beautiful views from the top deck."
Dog-friendly home with firepit, Hot tub, woodstove & 2 decks - walk to beach
Beach
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!
9.4 out of 10, Exceptional, (130)
"This bungalow is adorable and comfortable! The bed is really cozy and the fenced in yard was perfect for our bigger dogs. Great location, close to beaches and fun and Pamala was helpful and super fun to chat with. We will definitely be back!"
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!
Save an average of 15% on thousands of hotels when you're signed in
Oven, stovetop, dishwasher, cookware/dishes/utensils
Calistoga Dream Inn
Calistoga Dream Inn
Fridge, microwave, oven, stovetop
Wine Country Getaway
10.0 out of 10, Exceptional, (4)
"What a GREAT home!! We were so comfortable! I will definitely be booking this location again! Thank you for an awesome stay!"
The price is €490
includes taxes & fees
6 May - 7 May
Wine Country Getaway
Beach/ocean view
Romantic King Bed Studio ~ BEST VIEWS on Bodega Bay - We're right on the water!
9.4 out of 10, Exceptional, (289)
"Perfect getaway for our 23 anniversary. Thank you "
The price is €485
includes taxes & fees
2 Jun - 3 Jun
Romantic King Bed Studio ~ BEST VIEWS on Bodega Bay - We're right on the water!
Property grounds
Bella Fattoria-HBG Farm to Table Hideaway
10.0 out of 10, Exceptional, (14)
"The property was exactly as what we expected! It was a quiet, relaxing stay in the countryside. The house was clean and the check-in process was straightforward. We will be looking at returning to this place again in the future."
Bella Fattoria-HBG Farm to Table Hideaway
Fridge, microwave, oven, stovetop
3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006
10.0 out of 10, Exceptional, (94)
"5 adults stayed at this beautiful property located in the middle of a vineyard on a quiet country rode. Such a beautiful quiet location with spectacular sun rise AND sunset views. The photos of the home do this place no justice, it is simply perfect and quiet luxury. The front porch is so perfect for having coffee. Kristen was a great host and very responsive, even let us check in early! We hope to be back!!!"
3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006
Dining
Across from Marina, Fishing, Watch the Sea Lions, Great Parking for Boats
9.6 out of 10, Exceptional, (162)
"We thought the property was perfect with lots of room for all the family to stretch out."
Across from Marina, Fishing, Watch the Sea Lions, Great Parking for Boats
Fridge, microwave, oven, stovetop
Expansive ocean views along with privacy for this 2400 sf 3 bedroom 3 bath home
10.0 out of 10, Exceptional, (67)
"This property is excellent. Well-designed floor plan, ample common areas, large bedrooms and baths, and fully equipped kitchen in terms of high end appliances and kitchen equipment. The neighborhood is very nice and there are views of the bay from most of the rooms."
Expansive ocean views along with privacy for this 2400 sf 3 bedroom 3 bath home
Pool
4 Couple or 2/3 Families, Private w/Fantastic location, Views + Pool + Hot Tub
9.8 out of 10, Exceptional, (46)
"This beautiful home was wonderful for our extended families. The large open living area with a huge table and open kitchen made being together, talking and catching up so enjoyable while we cooked, and celebrated two birthdays. The outdoor area is lovely with plenty of seating, outdoor grills and pool with hot tub. Exquisite!"
4 Couple or 2/3 Families, Private w/Fantastic location, Views + Pool + Hot Tub
Beach nearby, sun-loungers
SETTING PRIVATE 2 blk toTown/River/Beach-Lg Deck+SPA-Mini Golf+Tennis+Coast12 mi
9.8 out of 10, Exceptional, (259)
"Girls trip to wine country. Perfect location and accommodations for 6 of us. Clare is super, we have stayed here twice."
SETTING PRIVATE 2 blk toTown/River/Beach-Lg Deck+SPA-Mini Golf+Tennis+Coast12 mi
TV, fireplace, DVD player, ping pong
Beautiful Single Level Home
10.0 out of 10, Exceptional, (176)
"Great location, well appointed property that had everything we needed for a golf getaway weekend. Close to the course, comfortable home. We'll be back!"
Beautiful Single Level Home
Property grounds
Wildwood Gardens Scenic Vacation Retreat on the River
9.6 out of 10, Exceptional, (165)
"At the end of our stay my friends and I agreed we would be back. It was a wonderful weekend enjoying beautiful clear skies with a view of the river during the day and next to the fire under stars at night. Loved the tiered deck and open grassy area. The hot tub was enjoyed by my friends. Inside was clean and cozy. We didn’t cook much but instead opted for pizza from downtown. Although the kitchen had everything we needed and the microwave and coffee pot appeared to be new the stove was slow to...
Wildwood Gardens Scenic Vacation Retreat on the River
Outdoor pool, a heated pool
Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8
10.0 out of 10, Exceptional, (12)
"We fully enjoyed our stay at this home. It had everything we needed to have a nice relaxing time in beautiful Calistoga. Would definitely stay again."
Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8
Outdoor dining
Wine Country Harvest Vacation Home
9.8 out of 10, Exceptional, (57)
"This was our second stay at the property. Very comfortable for our group of six. Easy access to wine tastings and great deli nearby for our picnic lunches"
Wine Country Harvest Vacation Home
Property grounds
Dog-friendly house with tranquil surroundings, deck, walk to the river
8.0 out of 10, Very good, (27)
"Amazing location, very walkable to town. Quiet and quaint. However, bathroom door was completely broken and cabinets in general could use some work. But rustic & charming is what I expected."
Dog-friendly house with tranquil surroundings, deck, walk to the river
Terrace/patio
Riverfront Home, close to beach and restaurants
9.8 out of 10, Exceptional, (90)
"This was a cute home and a great place to relax. I came with my mom to celebrate my birthday. It was great to have that quality time together. I thought the description of the place said we'd be staying on the ground floor. So, I was surprised when we had to climb a flight of stairs to get to our place. My mom is 89 years old, and was able to make it, but it was tiring for her. Overall, it was a nice and relaxing getaway weekend for both of us."
Riverfront Home, close to beach and restaurants
Exterior
Windsong - Romantic Retreat with Ocean View and Hot Tub located near 14th green.
9.6 out of 10, Exceptional, (197)
"We were so delighted with our stay at Birdsong. The home is even nicer than the photos convey. Beautiful setting on the golf course with pretty ocean views. The home is so comfortable. The architecture of the home is very custom and so marvelously laid out. It is spacious, high end finishes, nicely and comfortably furnished and the host(s) are so accommodating and friendly. We loved our stay and hope to come back next year."
Windsong - Romantic Retreat with Ocean View and Hot Tub located near 14th green.
Fridge, microwave, oven, stovetop
Glen Ellen Retreat #3 King Beds
10.0 out of 10, Exceptional, (27)
"A friend and I stayed just for one night after a winery spring event. We would love to have stayed longer! The home had everything we needed and more. It was clean and very well organized. The beds were beyond comfortable! We relaxed in the backyard on the patio and enjoyed the beautiful oak trees. I will be back for sure. Thank you!"
The price is €496
includes taxes & fees
5 May - 6 May
Glen Ellen Retreat #3 King Beds
Don't see what you're looking for?
See all available properties in Windsor
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.

Other property types in Windsor

Property grounds
Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, (77)
"Property was clean and had everything we needed for our wine weekend."
Cottage home near the Russian River; county parks; numerous wineries
Exterior
1890s Historic Gem: Casa Dela Esperanza - 6BD/4BA
10.0 out of 10, Exceptional, (3)
"This house was absolutely perfect for a girls get away weekend. It was so clean and beautiful and the host was super responsive and accommodating. I don't have a bad thing to say about this experience- it was absolutely perfect!!"
1890s Historic Gem: Casa Dela Esperanza - 6BD/4BA
Beach
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!
9.4 out of 10, Exceptional, (130)
"This bungalow is adorable and comfortable! The bed is really cozy and the fenced in yard was perfect for our bigger dogs. Great location, close to beaches and fun and Pamala was helpful and super fun to chat with. We will definitely be back!"
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!
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.

Windsor Holiday Homes information

Number of reviews
1,792
Accommodation
823 Holiday Homes
Lowest Price
€485
Highest Price
€496

Recent Reviews in Windsor
Expedia verified reviews