Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A covered patio is framed by wooden beams, offering a view of expansive vineyard landscapes and distant hills. Outdoor seating, including a dining table and lounge chairs, is arranged on the deck, inviting relaxation amid the tranquil scenery.
Guesthouse in Healdsburg
4.99 out of 5 average rating, 124 reviews

Bucher Vineyard Cottage

Discover the Charm of Our Vineyard Cottage! Escape to the heart of wine country with a stay at our fantastic one-bedroom cottage, nestled on the renowned Bucher Vineyard. Large room with kitchen & cozy seating area. Enjoy a restful night in a comfy queen bed surrounded by a stunning Redwood wall. Covered patio with heaters and fan. Deck with spectacular views of our vineyard & the Russian River Valley. Gas fire pit near deck. Hosts John & Diane are farmers and winery owners live on the property.

Guest favorite
The living area showcases a tufted gray sofa adorned with vibrant decorative pillows. A round mirror reflects light from a nearby window, while a wooden table adds character. A Smart TV is mounted on the wall, and a compact desk provides a workspace.
Apartment in Santa Rosa
4.93 out of 5 average rating, 202 reviews

1 Bedroom Garden Apmt, Smart TV/AC, 85 Walk Score

Escape to our charming 1-bedroom courtyard apartment, thoughtfully designed for a cozy and comfortable stay. The kitchenette is fully equipped with a retro-style refrigerator, countertop oven with air fry capabilities, double hot plate, electric frying pan, and a versatile marble table/island. Relax in the inviting living area with a full-size sofa, desk, and Smart TV, or step through the sliding door to enjoy your morning coffee at the bistro table overlooking the shared courtyard garden. The s

Top guest favorite
The exterior of a charming Victorian house is visible, featuring a welcoming front porch with a green door. Lush greenery and colorful plants frame the entrance, and a rustic wooden cart is placed nearby on a gravel pathway, enhancing the inviting outdoor space.
Home in Windsor
4.99 out of 5 average rating, 132 reviews

Gorgeous Victorian in the HEART of Windsor

Gorgeous renovated Queen Anne Victorian located in the heart of Windsor, CA combines quality finishes, modern convenience & vintage details. With a stylish kitchen, high ceilings, 3 beds/2 baths on a single level, HVAC & a huge lot with a Bocce Court. Walking distance to the Town Green, restaurants, wine tasting rooms and shopping. Just 3.5 miles from the Sonoma County Airport (STS), 5 miles to downtown Healdsburg, in the heart of the Russian River Valley & just 57 miles from the Golden Gate.

Guest favorite
A wooden bridge connects the ground to a treehouse elevated among tall trees. The treehouse features large windows and a circular design, surrounded by lush greenery. A sturdy netting lines the sides of the walkway, ensuring safety while traversing to this unique retreat.
Treehouse in Bodega Bay
4.95 out of 5 average rating, 210 reviews

Eagle's Nest Treehouse Farm Stay

Eagle's Nest Treehouse Farm Stay is a tranquil, secluded, luxurious, romantic wilderness experience in a private forest on a 400 acre working ranch. Thirty feet above the forest floor you are nestled in a gorgeous, well-appointed suite of 1,000 year old polished redwood, with bathroom and amazing copper/glass forest-view shower. Explore hiking trails through the forest and learn about ranch operations (Highland cattle, goats and ducks). See guest comments in the space description.

Top guest favorite
A spacious private deck is seen with views overlooking the rolling hills and valleys. Comfortable green lounge chairs are positioned for relaxation. The deck features wooden railing and steps leading down, while a doorway connects to the guest suite.
Guest suite in Santa Rosa
4.97 out of 5 average rating, 379 reviews

Wikiup lookout retreat

We self-developed our rural property as a secluded retreat with dog-friendly gardens. To share our creation with you, we designed a private 2nd-floor guest suite (ok to bring your good dogs). Your suite includes secure parking, private entrance, deck, kitchen, dining, living, 3 beds (queen, double, twin), one bath & a fenced back yard. We are on a country road near Healdsburg, Windsor, Russian River, Sebastopol, Santa Rosa, Calistoga, Sonoma & Napa valleys, wineries & beaches.

Top guest favorite
A bright and airy living space is presented, featuring large windows that allow natural light to fill the room. A cozy white sofa is complemented by a rustic coffee table made from logs. An indoor plant adds a touch of greenery, while soft textures create a welcoming ambiance.
Home in Graton
5 out of 5 average rating, 706 reviews

Eco Luxury Private Sanctuary / The Farmhouse Oasis

**Very Important** Please read description below and “Other things to note” at the bottom of this section before contacting us. • Adults Only • Private Sunny 1 Bedroom, 2 full bathroom 900 sq ft stand alone home • Private Backyard with Pool, Sauna, Outdoor Shower, and Outdoor Bathtub • Luxurious Modern Farmhouse Style • Created to feel like a boutique hotel experience • In the heart of wine country Sebastopol/ West Sonoma • Eco-Friendly products used • Strict cleaning protocols

Top guest favorite
The exterior of a rustic winery building is featured, characterized by its earthy tones and distinctive red door accents. Lush greenery and blooming purple flowers surround the structure, enhancing its natural setting. The building's design includes terracotta roofing and large windows that invite an abundance of natural light.
Farm stay in Healdsburg
4.97 out of 5 average rating, 679 reviews

Gracianna Winery Vineyard Loft - Farm Stay

Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile of Pinot Noir in Healdsburg includes equipped kitchen with new gas Wolf Range. Pick up breakfast needs before arriving. Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. LOFT AVAILABLE YEAR ROUND. TOT #3294N

Guest favorite
A spacious living area features a blue sofa adorned with a soft orange throw. A large area rug with intricate patterns anchors the space, while natural light floods in through large windows. A wooden coffee table rests centrally, complemented by decorative items.
Home in Windsor
4.96 out of 5 average rating, 439 reviews

Winelight Vineyard Home With Spa

Gated driveway, private, scenic, safe, secure, and impeccably clean. Unwind, prepare dinner on granite counter tops in this newly remodeled well-stocked gourmet kitchen. Enjoy plush amenities, fine decor, hot tub, romantic fireplace, French doors leading to outdoor decks, secluded rural vibe, reliably fast internet. Close to Sonoma County's best wineries, breweries and restaurants. There is a guest laundry, designer carport, and ample parking for guests.

Top guest favorite
A rustic cabin is nestled among towering redwood trees, featuring wooden shingles and large windows. A wooden deck, adorned with string lights, enhances the inviting exterior, while the natural landscape provides a serene backdrop. A gravel path leads to the entrance.
Cabin in Occidental
4.97 out of 5 average rating, 616 reviews

Rustic Yet Luxurious Cabin in the Redwoods

This rustic yet luxurious cabin is the perfect place to unplug. Walk through the woods, relax by a fire, and enjoy the food and wine of the Russian River Valley. 10 minutes from the beach. Minutes from Occidental, Graton, Forestville, and Guerneville. House has a full bathroom, bedroom downstairs with a Cal King bed and one upstairs with two twin beds. 5 acres in the redwoods, trampoline, fire pit area, high-speed Internet.

Guest favorite
A two-story home is presented with a light-colored exterior, complemented by large windows. A spacious driveway leads to the attached garage, while a covered porch area with seating is visible. The surrounding yard features low-maintenance landscaping and a wooden fence providing privacy.
Home in Santa Rosa
4.94 out of 5 average rating, 228 reviews

Centrally Located, Modern Wine Country Estate

Conveniently located in the heart of wine country! Just minutes away from famous wineries, breweries, world class-dining, family 'Epicenter', Sonoma County Airport and downtown Santa Rosa. This home features a gorgeous, new modern kitchen, outdoor dining area under the pergola with a BBQ and fire pit, pool table, washer and dryer, free wifi and parking. Welcome home! - Sincerely, Your Wine Country Concierge.

Top guest favorite
A hot tub is positioned on a grassy area, offering a view of rows of grapevines against a serene sunset. Colorful flowers are visible nearby, complementing the natural surroundings.
Home in Healdsburg
5 out of 5 average rating, 240 reviews

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court

Escape to a private and peaceful retreat surrounded by Russian River Valley Chardonnay and olive trees. Set on 10 acres of producing vines, our cottage offers vineyard views, a bocce court, fire pit, garden, cruiser bikes, and a sparkling hot tub. Immerse yourself in world-class food, wine, cycling, and nature. Your perfect wine country escape awaits!

Top guest favorite
The exterior of a charming cottage is framed by lush greenery and features a welcoming entrance with wooden doors. A stone pathway leads to the home, which is complemented by vibrant foliage and a pergola adorned with vines.
Home in Healdsburg
4.96 out of 5 average rating, 485 reviews

Dry Creek Valley Cottage

We live in a beautiful rural country setting but we are only a 5-7 minute easy drive into downtown Healdsburg where all the lovely shops, wineries and restaurants are. We invite you to enjoy our lovely garden and taste all the wonderful fruit when it is in season. We have apple, pear, peach, plum, pomegranate, persimmon and citrus trees.

Popular amenities for Windsor vacation rentals

When is the best time to visit Windsor?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$46,861 GYDG$47,070 GYDG$43,932 GYDG$41,631 GYDG$42,049 GYDG$46,233 GYDG$45,187 GYDG$42,677 GYDG$41,213 GYDG$43,514 GYDG$45,397 GYDG$45,815 GYD
Avg. temp10°C10°C11°C11°C12°C13°C14°C14°C15°C13°C12°C10°C

Frequently Asked Questions

  • What are the best places to stay in Windsor?

    Accommodations are found throughout Windsor, including homes near the Town Green or in quieter residential neighborhoods. Many options include outdoor spaces or proximity to parks, making it easy to relax and enjoy local life.

  • What are the best things to do in Windsor with kids?

    Families explore tree-shaded parks with play areas, picnic spaces, and community splash zones in Windsor. The town green often hosts family-friendly events, and nearby nature preserves provide spots for easy outdoor adventures.

  • What are some of the best things to do in Windsor?

    Explore local parks, attend community events on the Town Green, and visit nearby vineyards for tastings or tours. The area also has boutiques, markets, and picnic-friendly green spaces to enjoy throughout the year.

  • How is the weather in Windsor?

    Windsor has mild, wet winters around 44–56°F (7–13°C), and warm, dry summers often reaching 62–66°F (17–19°C). Layers and light rain gear are helpful, especially during cooler or rainy months.

  • When is the best time to visit Windsor?

    Late spring through early autumn is often recommended for mild temperatures, outdoor events, and vineyard scenery. Winter and early spring bring cooler weather and rain, but the area remains welcoming with quieter parks and tasting rooms.

  • What are the best places to visit in Windsor?

    Windsor Town Green is a lively gathering spot surrounded by shops and cafes, while local wineries invite exploration of Sonoma County flavors. Parks with trails and natural scenery provide spaces to relax or picnic.

  • What are some hiking trails in Windsor?

    Windsor has accessible nature trails in local parks, where visitors enjoy shaded walks, open meadows, and gentle loops suited for families. Nature preserves around the area offer more chances to spot native plants and birds along maintained paths.

  • What are some family activities we can do in Windsor?

    Families can enjoy picnicking and playgrounds in Windsor’s community parks, attend open-air movie nights, or take part in events on the Town Green. Seasonal farmers markets and easy nature walks are also popular with those traveling with children.

  • What are some of the best day trip ideas from Windsor?

    Consider exploring nearby vineyards with guided tours, relaxing along the Russian River, or enjoying scenic drives through rolling wine country landscapes. Nearby regional parks often have tranquil trails, picnic spots, and opportunities to spot local wildlife.

  • Are there any pet friendly accommodations available in Windsor?

    Many vacation rentals in Windsor welcome guests with pets, especially homes with fenced yards or those near parks. Be sure to check individual host policies for pet guidelines and amenities.

  • What are some local tips for visiting Windsor?

    Pack layers due to changing temperatures between morning and evening. Explore the local farmers market for fresh produce, and try to catch a community event at the Town Green to experience Windsor’s welcoming atmosphere.

  • What is Windsor known for?

    Windsor is known for its family-friendly parks, local wineries, and an active community scene centered around its town green. The area’s relaxed pace and proximity to Sonoma County vineyards are frequently highlighted.

  • What are the best hidden gems to explore in Windsor?

    Discover quiet corners in neighborhood parks, browse local art displays, or find family-run bakeries tucked along less-traveled streets. Small nature reserves around Windsor often provide peaceful trails and opportunities for birdwatching.

  • What are the best foods to try in Windsor?

    Windsor’s local restaurants often highlight regional ingredients like artisanal cheeses, seasonal fruits, and house-made baked goods. Wine country cuisine, wood-fired pizzas, and farm-fresh salads are frequently suggested choices.

  • What should I bring for a trip to Windsor?

    Pack layers for changing temperatures, comfortable walking shoes for exploring parks and town events, and sun protection for outdoor activities. Light rain gear is helpful during winter and spring months.

  • What is the nightlife in Windsor like?

    Nightlife in Windsor has a relaxed pace, with local wine bars, pubs, and venues featuring live music on select nights. Social spots often cluster around the Town Green, where community events occasionally continue into the evening.

  • What are the most popular events or festivals in Windsor?

    Windsor's Town Green hosts a summer concert series, a farmers market during warm months, and community celebrations in late spring and around autumn harvest time. Holiday-themed festivals and outdoor movie nights are also frequently suggested.

  • Are there family friendly vacation rentals in Windsor?

    Windsor has a range of family-friendly vacation rentals, including spacious homes with multiple bedrooms, kitchens, and outdoor play areas. Many are located near parks or in peaceful residential neighborhoods.

Quick stats about vacation rentals in Windsor

  • Total vacation rentals

    Explore 360 vacation rentals in Windsor

  • Nightly prices starting at

    Windsor vacation rentals start at G$6,276 GYD per night before taxes and fees

  • Verified guest reviews

    Over 7,980 verified reviews to help you choose

  • Family-friendly vacation rentals

    260 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    280 properties feature pools

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wi-Fi availability

    350 of Windsor vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Windsor rentals

  • 4.9 Average rating

    Windsor stays are highly rated by guests—averaging 4.9 out of 5!

Destinations to explore

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