Windsor Holiday Rentals from NZ$161: Search Short-Term Rentals

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Windsor holiday rentals

A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

1. Sauna, Cold Plunge & Fire Pit Near Wineries

Windsor

Keri S.

includes taxes & fees

8 Nov - 9 Nov

A kitchen with a granite countertop, a fruit bowl, and a dining area with chairs and a table.

2. Elegant Vineyard Living at a Private Wine Country Estate

Windsor

Eric B.

includes taxes & fees

8 Nov - 9 Nov

A swimming pool with lounge chairs, a covered area, and a building with a gabled roof.

3. Tuscan by Onalani 2x3BR Year-round pools & hot tubs

Windsor

includes taxes & fees

28 Nov - 29 Nov

A cozy cabin with a loft bedroom, wooden exterior, and a small balcony.

4. Wildhaven Sonoma Glamping

Healdsburg

NEERJA

includes taxes & fees

8 Dec - 9 Dec

A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

5. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Healdsburg

Mark R.

includes taxes & fees

2 Dec - 3 Dec

6. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Northwest Santa Rosa

kevin c.

includes taxes & fees

9 Nov - 10 Nov

A hallway with white paneling and wooden doors, leading to an outdoor area with greenery.

7. 2BR Bungalow - Russian River & Wine Country

Forestville

Greg K.

includes taxes & fees

8 Nov - 9 Nov

A modern living room with a blue sectional sofa, a wooden coffee table, and a staircase leading to another room.

8. Serenity at the Russian River

Mirabel Heights

Patricia A.

includes taxes & fees

12 Nov - 13 Nov

A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

9. The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

Forestville

Rebecca I.

includes taxes & fees

12 Nov - 13 Nov

An outdoor patio with wooden chairs and a table, surrounded by greenery and a white pergola.

10. Peaceful, charming, cottage in wine country. Beautiful yard!

Sebastopol

Brandi K.

includes taxes & fees

8 Nov - 9 Nov

A natural landscape with a lake, trees, and hills.

11. The Ranch at Lake Sonoma

Geyserville

Epeli

includes taxes & fees

11 Nov - 12 Nov

A deck with outdoor seating, a grill, and a view of a house with large windows.

12. Somms Rest ⎮ Designed. Curated. Peaceful.

Mirabel Heights

Jana P.

includes taxes & fees

11 Nov - 12 Nov

A room with a brown sofa, two wicker chairs, a small table, and a lamp.

13. Hideaway Cottages

Calistoga

includes taxes & fees

16 Nov - 17 Nov

A swimming pool with a slide, a barbecue area, and a wooden deck.

14. 2 Hidden Wine Country Gem Upstairs Unit

Scenic Brush Creek

Glen M.

includes taxes & fees

16 Nov - 17 Nov

A patio area with a stone floor, outdoor seating, and a house in the background.

15. Sebastopol Lux Walk toTown Guest Suite

Sebastopol

Brad

includes taxes & fees

16 Nov - 17 Nov

A wooden interior with a dining area, a bench, and a mirror on the wall.

16. Cozy Riverfront Cabin - Beach Access & Wood Stove

Guerneville

Jehanne H.

includes taxes & fees

8 Nov - 9 Nov

A spacious living room with a wooden ceiling, large windows, and a sectional sofa.

17. Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C

Forestville

Ellen B.

includes taxes & fees

9 Nov - 10 Nov

A living room with a stone fireplace, wooden flooring, a dining area with chairs, and a large window.

18. Wine Country Getaway

Mirabel Heights

Rachel S.

includes taxes & fees

8 Nov - 9 Nov

A beach with a large rock formation, a sandy shore, and a calm sea.

19. The Tiny Tipsy Turtle

Guerneville

ANTHONY B.

includes taxes & fees

10 Nov - 11 Nov

An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

20. Russian River Brew-cation Home

Northwest Santa Rosa

Gina N.

View all properties

Find holiday rentals that suit your style

Top Windsor Hotel Reviews

A fountain with water spouting from the top, surrounded by a circular pool.

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Windsor

10/10 Excellent

Karen

An outdoor patio with stone walls, wooden pergola, and multiple tables and chairs under beige umbrellas.

Hilton Garden Inn Sonoma County Airport

Santa Rosa

10/10 Excellent

Anonymous traveller

A spacious living room with a large window, a sofa, a coffee table, and a plant.

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

Santa Rosa

10/10 Excellent

Ethan

A table set with a cheese board, wine glasses, and bottles, with a green sofa and lush greenery in the background.

Calderwood Inn

Healdsburg

10/10 Excellent

JR

An outdoor seating area with wooden lattice walls, chairs, and tables, featuring string lights.

Hotel Vinea, a Travelodge by Wyndham

Healdsburg

10/10 Excellent

Really good stay. Check-in was straightforward, the room was a decent size and really clean and nice. Bed was big and very comfortable. Would have been better if there was a bit more crockery and utensils in the room. Wine glasses and cutlery particularly. Free continental breakfast was nice. Interestingly, the rooms are not sound proof, found that the hard way at night and hearing my neighbours going at it!

Anthony

A hotel room with two beds, a red armchair, a large window with a view, and abstract wall art.

Best Western Plus Wine Country Inn & Suites

Santa Rosa

10/10 Excellent

Anonymous traveller

A modern living room with a brown leather sofa, a coffee table with a bottle and glasses, and a large abstract painting on the wall.

Fairview Inn and Suites

Healdsburg

10/10 Excellent

David

A fountain surrounded by a brick pathway, with a building featuring a tiled roof and ivy-covered walls in the background.

Vinarosa Resort & Spa

Santa Rosa

10/10 Excellent

Simone

A multi-story hotel with a modern facade, balconies, and a prominent entrance.

Art House Hotel and Suites

Downtown Santa Rosa

10/10 Excellent

Michael

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as NZ$161 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find holiday rentals in Windsor?

Yes, there are holiday rentals in Windsor close to Powell's Sweet Shoppe - Windsor, 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 top-notch restaurants and wineries. 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?

DOG-FRIENDLY, COZY—PERFECT 4 COUPLES—Close to EVERYTHING. SPECIAL DISCOUNTS!: This holiday home rental outside of Windsor is located on the waterfront, and has a balcony, a selection of books and a Smart TV to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Windsor?

Choose from 30 Expedia holiday rentals in Windsor for a memorable holiday.

What can I see and do in Windsor?

Cultural attractions include Pacific Coast Air Museum, whereas Russian River is a spot to enjoy nature. Windsor Golf Club and Windsor Oaks Vineyards 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.

Windsor Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor holiday rentals

1. Sauna, Cold Plunge & Fire Pit Near Wineries

2. Elegant Vineyard Living at a Private Wine Country Estate

3. Tuscan by Onalani 2x3BR Year-round pools & hot tubs

4. Wildhaven Sonoma Glamping

5. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

6. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

7. 2BR Bungalow - Russian River & Wine Country

8. Serenity at the Russian River

9. The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

10. Peaceful, charming, cottage in wine country. Beautiful yard!

11. The Ranch at Lake Sonoma

12. Somms Rest ⎮ Designed. Curated. Peaceful.

13. Hideaway Cottages

14. 2 Hidden Wine Country Gem Upstairs Unit

15. Sebastopol Lux Walk toTown Guest Suite

16. Cozy Riverfront Cabin - Beach Access & Wood Stove

17. Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C

18. Wine Country Getaway

19. The Tiny Tipsy Turtle

20. Russian River Brew-cation Home

Find holiday rentals that suit your style

Top Windsor Hotel Reviews

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

10/10 Excellent

Find out more about Windsor

Windsor holiday rentals: An excellent choice for every season

How to find incredible deals on Windsor rentals

Frequently Asked Questions

Can I find holiday rentals in Windsor?

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

How many holiday rentals are there in Windsor?

What can I see and do in Windsor?

What are holiday rentals like in Windsor?