
Vacation rentals in Windsor
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Top-rated vacation rentals in Windsor
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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.

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

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.

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.

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.

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

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

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.

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.

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.

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!

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
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Wine Country Cottage Escape
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$46,861 GYD | G$47,070 GYD | G$43,932 GYD | G$41,631 GYD | G$42,049 GYD | G$46,233 GYD | G$45,187 GYD | G$42,677 GYD | G$41,213 GYD | G$43,514 GYD | G$45,397 GYD | G$45,815 GYD |
| Avg. temp | 10°C | 10°C | 11°C | 11°C | 12°C | 13°C | 14°C | 14°C | 15°C | 13°C | 12°C | 10°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!
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