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Holiday houses in Windsor

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Quick stats about holiday rentals in Windsor

  • Total holiday rentals

    Explore 80 holiday rentals in Windsor

  • Nightly prices starting at

    Windsor holiday rentals start at $42 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,040 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Windsor holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Windsor rentals

  • 4.7 Average rating

    Windsor stays receive an average rating of 4.7 out of 5 from guests

Top-rated holiday rentals in Windsor

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

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Superhost
A globe rests on a polished surface, accompanied by a wooden 'Hello!' sign. Sheer curtains filter soft light, creating a bright and welcoming scene. The composition offers a blend of decorative elements that enhance the living space.
Home in South Windsor

Spacious 3 Bedroom Ranch With Office

Forget your worries in this spacious and serene space with room for 8. The entire first floor is yours to enjoy and there aren’t any shared spaces. Relax in the backyard or on the porch. 2 full bathrooms are yours to relax and enjoy. There’s a freshly remodeled bathroom in the master bedroom with walk in shower and a bathtub in the 2nd bathroom. Fully stocked kitchen awaits your inspiration. Much shopping awaits you and all the store are within 10 minutes away from you. BDL is 20 minutes away,

4.86 out of 5 average rating, 198 reviews
Superhost
A bright workspace features a wooden desk with a black chair, positioned against a light-colored wall. Two framed botanical prints are displayed above the desk, complemented by a standing lamp. A mirror reflects the scene, while a potted plant adds a touch of greenery.
Apartment in Windsor Locks

Apt near Big E, Six Flags, Bradley airport

Welcome to our charming and stylish upstairs apartment, perfect for a cozy retreat! Enjoy the privacy of having the entire space to yourself. Access the apartment directly through the back entrance, up the outdoor staircase. We're conveniently located just a 10-minute drive from Bradley International Airport. Inside, you'll find: - A comfortable bedroom with a Queen-sized bed, complete with fresh linens - A fully stocked kitchen, equipped: Pots, pans, baking dishes, etc Washer and dryer

4.82 out of 5 average rating, 203 reviews
Guest favourite
A spacious outdoor area is showcased, featuring a well-maintained lawn and a wooden deck leading to a white, single-story house. Surrounded by trees, the private yard includes a white picket fence, providing a sense of seclusion.
Guest suite in South Windsor

Premium Private Suite • Entry • Wrkspace • Parking

Welcome 🙏 to our premium private guest suite, designed for comfort, privacy, and a seamless stay. Enjoy a spacious, hotel-style retreat with a separate private entrance, easy self check-in, fast Wi-Fi, dedicated workspace, and free parking—ideal for couples, business travelers, and extended stays. Quiet, beautifully maintained, and thoughtfully designed for an stress-free experience 😊. **NO SMOKING of any kind (including cigarettes, vaping, e-cigarettes, marijuana, or any substances).

4.88 out of 5 average rating, 301 reviews
Guest favourite
Cottage in Windsor

In-law apartment in Farmington River Cottage

If you are craving a getaway with a special someone, this space is meticulously clean and an opportunity to practice social distancing while relaxing and enjoying the Farmington River. Only 15 minutes from Bradley airport, 5 minutes from the train and I91. Nature, dining, all within a comfortable drive. You get it all here! Private space with its own entrance, one bedroom and newly updated bathroom, a cozy living room with fireplace in a Garden Level Unit. Off street parking available.

4.89 out of 5 average rating, 222 reviews
Guest favourite
A modern kitchen and dining area showcase contemporary cabinetry and stainless steel appliances. A round table with four chairs is set for meals, complemented by decorative placemats. Natural light enters through the entryway, which features a glass door, enhancing the bright atmosphere of the space.
Apartment in Simsbury

Newly Renovated 2 Bedroom in Heart of Tariffville

Welcome to Center Street Stay, a second story charming retreat in Simsbury, CT. This fully renovated two-bedroom apartment blends modern comfort with convenience. The kitchen is equipped with modern appliances, perfect for culinary endeavors. Relax in the living area with a smart TV or get some rest on the memory foam mattresses. The renovated bathrooms offers sleek fixtures and a rejuvenating shower. Enjoy amenities like a dedicated workspace, in-unit washer/dryer, high-speed Wi-Fi.

4.92 out of 5 average rating, 36 reviews
Guest favourite
A spacious living area features a red sectional sofa and a small round coffee table with a plant centerpiece. The open layout connects to a well-lit kitchen in the background, visible through a doorway, blending comfort and functionality.
Home in Manchester

Charming Cape Home, Close to All

Charming Cape Home in the Heart of Connecticut Enjoy comfort and convenience just 20 mins from Bradley Airport, 10 mins from Hartford, 25 mins from UConn, and 40 mins from New Haven. Nestled on a quiet residential street, our cozy home features multiple beds, fast Wi-Fi, Smart TVs, central air, and a fenced backyard with patio and fire pit. Grocery stores, restaurants, and coffee shops are just 5 minutes away. A perfect retreat for families, professionals, or campus visits!

4.9 out of 5 average rating, 119 reviews
Guest favourite
A spacious living area features high ceilings with exposed beams and wooden flooring. Comfortable seating includes sofas and chairs arranged around a central coffee table. A large television is set against one wall, and plants add a touch of greenery to the room.
Home in Windsor

A Tranquil Getaway Wrapped in Island Vibes

Come and enjoy a relaxing stay in this charming home with a warm island-inspired atmosphere. Featuring 3 bedrooms and 2 bathrooms, this spacious retreat comfortably accommodates up to 8 guests. The large kitchen and open living area provide plenty of space for family and friends to gather, dine, and create lasting memories. Located in a quiet suburban neighborhood just outside downtown Hartford, the home offers the perfect balance of convenience and tranquility.

4.92 out of 5 average rating, 111 reviews
Top Guest favourite
A stone exterior corner of the home presents a covered porch with white railings. The adjacent grassy area leads to a serene river view, where trees surround the water's edge, reflecting the soft light of the sky.
Home in Windsor

Relax By The Water

Take it easy at this unique and tranquil getaway. Just 20 minutes from downtown Hartford, 5 minutes from Bradley airport, and conveniently close to the Loomis Chaffee school, you’ll have our entire two bedroom, two bath riverfront home to enjoy. Take in the views from the expansive balcony, enjoy a meal in the waterside dining room, or work from home in the dedicated office space. Two queen beds and a sleeper sofa sleep six comfortably. Don’t miss it!

4.96 out of 5 average rating, 79 reviews
Top Guest favourite
Guest suite in East Granby

10 Hillcrest

So we were offline for a few months but we now have a totally new remodeled space. Lots more light and upgrades we think you will enjoy! The perfect location! Private enough to see trees and birds and yet close enough to jump on the highway to anywhere. Conveniently located on a dead end street! Many, many farms, wineries, breweries and eateries just minutes down the road. We are also just minutes from Bradley International Airport

4.85 out of 5 average rating, 434 reviews
Guest favourite
A spacious living area features a large sectional sofa adorned with decorative pillows, offering comfortable seating. Large windows allow natural light to fill the room, highlighting the wooden floor and a coffee table at the center. A warm ambiance is complemented by tasteful artwork on the walls.
Home in Windsor

Quiet Comfy Getaway 3 BR Home | Close to BDL

Welcome to our newly renovated 3-bedroom home in Windsor, CT! Sleeps up to 8 guests and is perfect for families, business travelers, healthcare professionals, and extended stays. Enjoy fast WiFi, a dedicated workspace, fully equipped kitchen, complimentary coffee bar, washer/dryer, free parking, and spacious bedrooms. Minutes from Hartford, Bradley Airport (BDL), hospitals, shopping, dining, and major highways.

4.94 out of 5 average rating, 123 reviews
Top Guest favourite
Home in Windsor Locks

The Hangar

Welcome to The Hangar, a newly remodeled (2025) travel-themed stay just minutes from Bradley International Airport. With aviation-inspired décor, modern finishes, and thoughtful amenities, this home is perfect for business travelers, flight crews, and families alike. Relax, recharge, and enjoy stress-free access to Hartford, Springfield, and beyond.

4.96 out of 5 average rating, 54 reviews
Top Guest favourite
A bright living area features a dark sofa with multiple cushions, flanked by two patterned chairs. A wooden coffee table is positioned in the center, and a laptop is placed on it. Natural light enters through the two windows, adorned with dark curtains.
Apartment in Enfield

FROG Suite Apartment

Welcome to the FROG Suite apartment, the prefect place in a comfy private space. Be it for work, pleasure, travel or leisure, this alluring updated space is located upstairs over the garage in a quiet residential neighborhood and includes a private keyless entry door lock. Apartment is located upstairs over the garage and is attached to the house.

4.99 out of 5 average rating, 344 reviews

Popular amenities for Windsor holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Stay near Windsor's top sights

Nomads Adventure Quest

11 locals recommend

University of Hartford

11 locals recommend

Northwest Park

6 locals recommend

Gillette Ridge Golf Club

4 locals recommend

Back East Brewing

4 locals recommend

Windsor Historical Society

3 locals recommend

Other great holiday rentals in Windsor

Guest favourite
Guesthouse in Windsor

Your New England Summer Getaway!

4.98 out of 5 average rating, 44 reviews
Guest favourite
A spacious kitchen features wooden cabinetry with glass accents, contrasting with granite countertops. Stainless steel appliances, including a refrigerator and oven, are showcased. Natural light fills the room through a large window above the sink, enhancing the warm colours of the cabinetry and countertop.
Home in Windsor

By The River

4.97 out of 5 average rating, 75 reviews
Guest favourite
The spacious bedroom features a large bed with a navy blue comforter, complemented by two decorative pillows. A dark wooden dresser and two nightstands with lamps are present. Natural light enters through a window and a skylight above. A geometric patterned area rug enhances the floor space.
Home in East Hartford

Family Retreat Near Hartford – Year-Round Getaway

4.97 out of 5 average rating, 36 reviews
Guest favourite
Home in South Windsor

Pet Friendly Cozy Home for Work/Leisure

4.85 out of 5 average rating, 26 reviews
Guest favourite
A dining area features a round wooden table surrounded by six gray chairs. A white vase filled with fresh flowers is placed center stage. A staircase with a black railing leads to an upper level, while an open kitchen is visible in the background.
Home in Bloomfield

The Majestic View | Luxury Stay Golf Views

4.89 out of 5 average rating, 47 reviews
Superhost
The entrance features a bright white door with a round window, surrounded by tall potted plants. A wooden mat is positioned at the door, and the number 31 is displayed prominently beside it. The setting is framed by a porch with railings.
Home in Windsor Locks

The Lily Pad • Family-friendly • Sleeps 14 • BDL

4.74 out of 5 average rating, 139 reviews
Top Guest favourite
A daybed with intricate black detailing is adorned with an array of decorative pillows in various patterns. A colorful piece of wall art complements the space. Natural light streams through the window, which is fitted with light-filtering shades, illuminating a soft area rug beneath.
Apartment in Bloomfield

Bloomfield Bungalow

4.98 out of 5 average rating, 58 reviews
Guest favourite
A living room is presented featuring a couch, two chairs, and a wooden coffee table. A television is positioned atop a side table, while a decorative plant adds a natural element. Soft light filters through sheer window curtains, creating a warm ambiance.
Home in South Windsor

Grampa Potatoes Homestead LLC

4.86 out of 5 average rating, 78 reviews

When is the best time to visit Windsor?

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Frequently Asked Questions

  • What are the best places to stay in Windsor?

    Windsor’s downtown neighborhoods and areas near parks are popular for a blend of convenience and quieter surroundings. Many guests choose residential streets with tree-lined views and easy walking access to local dining or historical sites.

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

    Children often enjoy the farm animals and nature center at Northwest Park, hands-on exhibits at the Windsor Historical Society, and open play areas in community parks. Seasonal family festivals and craft events add to the options.

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

    Explore Northwest Park for walking trails and wildlife habitats, visit the Windsor Historical Society for stories of the town’s past, and browse local shops in Windsor Center. Community events and outdoor recreation round out popular activities.

  • How is the weather in Windsor?

    Windsor has cold winters around 19–35°F (-7–2°C) and warm summers reaching 64–85°F (18–30°C). Spring and autumn bring milder temperatures and increased rainfall, so a mix of clothing layers and rain gear is practical year-round.

  • When is the best time to visit Windsor?

    Late spring through early autumn is often recommended for milder temperatures, outdoor festivals, and lush park scenery. Fall foliage is a regional highlight, while winter stays invite cozy activities and historic museum visits.

  • What are the best places to visit in Windsor?

    Explore the Windsor Historical Society for local history exhibits, stroll through Northwest Park’s natural spaces, or visit the historic Windsor Center for unique shops and dining. Outdoor areas and museums are frequently suggested by visitors.

  • What are some hiking trails in Windsor?

    Northwest Park has well-maintained walking and hiking trails through forests, meadows, and wetlands, suitable for a variety of abilities. Some parks in the area include interpretive signage about local wildlife and plant life.

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

    Families frequently explore interactive exhibits at the Windsor Historical Society, picnic or hike at Northwest Park, and attend storytimes or workshops at local libraries. Outdoor playgrounds and farm visits add to the experience for children.

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

    Many visitors explore nearby river towns for art galleries, historic sites, and scenic parks, or head toward Hartford for museums and cultural performances. Nature trails and state parks around the area draw those interested in hiking or wildlife observation.

  • Are there any pet friendly accommodations available in Windsor?

    Windsor has a variety of pet friendly accommodations, especially in residential neighborhoods and near local parks. Many hosts welcome guests traveling with animals, so it is helpful to check listing details or message hosts about your pet’s needs.

  • What are some local tips for visiting Windsor?

    Consider stopping by local farmers’ markets for fresh produce, or checking community calendars for seasonal events. Early mornings in the parks can be particularly peaceful, and historic districts often feature walking tour routes.

  • What is Windsor known for?

    Windsor is known for its heritage as one of Connecticut’s oldest towns, with preserved historic sites and scenic riverfront landscapes. The community often highlights its colonial era history and thriving parks.

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

    Discover the Connecticut Valley Tobacco Museum for insight into local agricultural traditions, or explore quiet trails and birdwatching at Northwest Park. Local shops and cafes in historic Windsor Center can also provide a unique experience.

  • What are the best foods to try in Windsor?

    Local menus feature classic New England dishes such as clam chowder, baked goods made with regional fruit, and comfort foods found in neighborhood diners. During the harvest season, you can frequently sample corn, apples, and maple products from area farms.

  • What should I bring for a trip to Windsor?

    Pack clothing layers for temperature changes, a waterproof jacket for unexpected rain, and comfortable shoes for exploring parks or walking through historic districts. In summer, sunscreen and insect repellent are helpful for outdoor activities.

  • What is the nightlife in Windsor like?

    Windsor’s nightlife is relaxed, with locally owned restaurants, taverns, and occasional live music around town. Social events and gatherings often center near Windsor Center and community venues.

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

    Windsor is known for community gatherings that often highlight local culture, history, and seasonal traditions. Annual events frequently suggested include outdoor summer concerts, agricultural fairs, and multicultural celebrations.

  • Are there family friendly vacation rentals in Windsor?

    Windsor has a range of family friendly vacation rentals, with options near parks, schools, and residential neighborhoods. Many homes include features like multiple bedrooms, kitchens, and access to outdoor spaces.

Destinations to explore