Photo by Jennifer Hill

Holiday Rentals in Windsor

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Holiday Rentals in Windsor

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

9.8 out of 10, Exceptional, (419)
"We stayed at aftermath years ago and it was just as spectacular this time. The views of the ocean are amazing as you have a front row seat to watch the waves crash on the beach right below. The ocean rocks you to sleep in the evening. If you get a chance to come stay- bring all the provisions you need and just enjoy this sweet spot. You won’t want to leave "
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

Panoramic Ocean View--3 Min Walk To Beach

9.6 out of 10, Exceptional, (294)
"This was the perfect place for a quick mid-week getaway for my son and I (and our dog). Location was great. I had never been to Dillon Beach but now that I know how peaceful and serene it is, we will be back.The house was adorable. From the moment we walked in and saw the ocean views from the living room and the deck, we were hooked. Not only are the views amazing, the walk down to the beach was very easy and the beach itself was clean and not crowded at all. This is not the place to come if...
Panoramic Ocean View--3 Min Walk To Beach

Oceanfront - Hot Tub - Newly Remodeled Cottage

9.8 out of 10, Exceptional, (365)
"The house location and view were fantastic. The appliances and sinks and faucets were all very nice. I have never encountered pop out electrical receptacles before. There are some low ceilings in the bathroom, kids bedroom and the television room. But these are easily managed. The morning of our 3rd day we had ants on the counter next to the sink. Interesting, because there was never any food there. But they were quickly dispatched. The hot tub was fantastic. What a view overlooking the...
Oceanfront - Hot Tub - Newly Remodeled Cottage

New Modern House in Sonoma Valley's Best Area

10.0 out of 10, Exceptional, (243)
"Eric’s house and location is amazing. From the wildlife that walks past the full length sliding doors, the stream that runs through the property to the close proximity to all the many vineyards in the Sonoma and Napa region. Eric leaves a detailed list of all the activities and dining the area has to offer. A must stay. "
New Modern House in Sonoma Valley's Best Area

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

10.0 out of 10, Exceptional, (248)
"Very comfortable and welcoming. The owner put a lot of thought into the property. The view is killer and the beach is a short walk away where we took our dog to play.We can’t wait to go back do"
Romantic, Dramatic Views! Full calendar https://www.vrbo.com/81742?dateless=true

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

10.0 out of 10, Exceptional, (59)
"Villa Montebella is a wonderful place for a large group. Our families stayed at the Villa over the Thanksgiving Holiday week to celebrate our Daughter’s Napa Wedding. The pictures are accurate, but do not do the property justice. The place is Stunning! There are many comfortable and secluded bedrooms and facilities. The wine cave was amazing and we hired Chef Adair for a special rehearsal dinner there. We have an active group and took advantage of the many amenities. The media room was perfect...
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

COZY Bungalow--Dog-Friendly—Perfect for Couples!!!

9.6 out of 10, Exceptional, (167)
"We had a lovely stay. The space was perfect for two people and a dog. So central to hikes and fish shacks nearby. Pamela was easy to communicate with and is a great host. "
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!

Bodega Bay - Magical Ocean Front View- Doesn’t get better than this!!

9.8 out of 10, Exceptional, (161)
"Absolutely loved this home its decor, its amenities and location. Also, loved that the 3 bedrooms are in separate locations in the house, giving everyone privacy if you happen to bring guests to stay. It's a short drive to Bodega bay restaurants as well. We will definitely stay here again."
The price is €1,083
includes taxes & fees
13 Mar - 14 Mar
Bodega Bay - Magical Ocean Front View- Doesn’t get better than this!!

4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'

9.2 out of 10, Wonderful, (166)
"Great house with lots of amenities. Also had a pool table and a video game console. Good location with an excellent view of the sunset when not foggy. Our family had a great time and we would stay there again in the future."
4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'

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

9.4 out of 10, Exceptional, (325)
"The driveway is a little tricky especially getting out. It’s narrow and uphill and dumps you onto highway one. The transition from driveway to highway made both my rear tires spin trying to get out while cars are already traveling 45mph "
The price is €526
includes taxes & fees
13 Mar - 14 Mar
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!

Double Queen Room Non-vaulted with Ocean View!

9.2 out of 10, Wonderful, (5)
"Great location, very quiet and it has a beautiful view. The room was perfect and dog friendly. "
The price is €198
includes taxes & fees
13 Mar - 14 Mar
Double Queen Room Non-vaulted with Ocean View!

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

9.0 out of 10, Wonderful, (280)
"We really enjoy this house "
Ocean Front/3 minute walk/Hotub/Sauna/Pets/Massage Chair/Pinball/Pac-Man Machine

Ocean view easy access to Doran Beach, Golf course and Bluewater Bistro.

10.0 out of 10, Exceptional, (70)
"The house was very warm and comfortable. Clean and had just about everything we needed. Close walk to the beach and relaxing views"
Ocean view easy access to Doran Beach, Golf course and Bluewater Bistro.

Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views

8.4 out of 10, Very good, (22)
"Our stay was overall really good.We did get a very wet weekend and we didn't know that to go from the kitchen to the rooms/bathroom we had to pass through the open patio, so we'd get wet and the floor got soaked as we came in and out.Other than that we had a lovely stay! The hot tub worked well, we watched DVDs and were able to prepare all our meals.I'd definitely come back."
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH

9.2 out of 10, Wonderful, (194)
"This was an awesome spot, couldn't recommend it more :)"
The price is €830
includes taxes & fees
24 Mar - 25 Mar
ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH

Panoramic Ocean Views walk to the Beach

10.0 out of 10, Exceptional, (1)
"We had a wonderful stay at this property perched on a hillside above Dillon Beach. The house is 360 views you can watch the sunrise and sunset from this location. The mountain has deer, hawks, bunnies. The house had all the amenities you'd need for a dinner. The house is perched on a hill so you will get a workout in and need to be in good shape. The house has about 90 steps up so it's a bit of a haul for luggage and groceries but I thought worth it because of the view. "
Panoramic Ocean Views walk to the Beach

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

9.8 out of 10, Exceptional, (310)
"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!

'Wabi Tei' Serenity with Panoramic Ocean View. Hot Tub, BBQ, XBOX, WiFi, Pets OK

9.6 out of 10, Exceptional, (132)
"Absolutely stunning home located a quick drive or moderate walk to beach. My family and I were in awe of the impeccable views of the ocean which we enjoyed from a multitude of vantage points. There was plenty of seating for everyone to enjoy comfortably. As well as ample sleeping space available. My mother said she felt like a Queen in the master suite. We made a few family meals in the incredibly well equipped kitchen. We also appreciated a soak in the hot tub. The walk to the beach was very...
'Wabi Tei' Serenity with Panoramic Ocean View. Hot Tub, BBQ, XBOX, WiFi, Pets OK

The Tiny Tipsy Turtle

2.0 star property
10.0 out of 10, Exceptional, (13)
"Cute little place in a great location that is within walking distance of restaurants/bars in the area. National Park just a few minutes away. Host is very responsive. "
The price is €199
includes taxes & fees
16 Mar - 17 Mar
The Tiny Tipsy Turtle

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

10.0 out of 10, Exceptional, (220)
"This is our second time renting Willian's home in Kenwood. This home is absolutely stunning and fully equipped with everything you need for a family or group of friends gathering. Fold-out bunk beds, 3 pack and plays, a high chair, tennis and pickle ball rackets, sidewalk chalk and great kitchen and bathroom products. Linens are great quality as well. Chateau St Jean and many other wineries are minutes away. We will absolutely rent this home again and will recommend it to others.Only issue is...
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
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 types of properties in Windsor you may be interested in

Holiday Inn Windsor Wine Country by IHG

3.0 star property
9.0 out of 10, Wonderful, (898)
"As always great place, love the suites with a great price. Breakfast is always yummy. Love holiday inn! The service desk is amazing! Staff are the sweetest! I've been here 5 times during the holidays. Hopefully they keep everything as it is. Ps.suites have jetted king size tubs."
The price is €121
includes taxes & fees
14 Mar - 15 Mar
Holiday Inn Windsor Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

2.5 star property
9.2 out of 10, Wonderful, (1001)
"I pretty much liked the entire property. The staff was very kind and very friendly. The people that ran the morning breakfast were very clean and efficient."
The price is €154
includes taxes & fees
29 Mar - 30 Mar
Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Hampton Inn & Suites Windsor - Sonoma Wine Country

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Very nice clean updated Hampton Inn - close by to vineyards and Healdsburg"
The price is €142
includes taxes & fees
23 Mar - 24 Mar
Hampton Inn & Suites Windsor - Sonoma Wine Country
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

Can I find holiday rentals in Windsor?

Yes, there are holiday rentals in Windsor close to Dom Whitney Tasting Lounge, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Windsor has a good selection of wineries and top-notch restaurants. Make sure you have time to check out the festivals while you're in the area.

What are some of the best holiday rentals that Windsor has to offer?

COZY Bungalow--Dog-Friendly—Perfect for Couples!!! : This holiday home rental outside of Windsor is located on the waterfront, and offers a selection of books, a Smart TV and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Windsor?

Choose from 44 Expedia holiday rentals in Windsor for a memorable holiday.

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 Sonoma-Cutrer Vineyards Cutrer Vineyard are other places to visit while you're in town.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for families.