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Holiday rentals 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 ₹2,874 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    80 of Windsor holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi 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
4.89 out of 5 average rating, 192 reviews

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,

LocationValueHeating

Superhost
A cozy studio space features a spacious bed with a light coverlet and decorative pillows. A neutral rug lies beneath, complementing the wooden flooring. Decorative wall art and plants are displayed throughout, while a workspace with a desk and chair is neatly arranged nearby.
Flat in East Windsor
4.86 out of 5 average rating, 123 reviews

Modern Cozy Studio

Experience the perfect stay in this cozy studio, nestled in the heart of Broad Brook. You'll be conveniently close to local restaurants, the Opera House, and just a short drive from Bradley International Airport, Hartford, CT, and Springfield, MA. Plus, we're pet-friendly! Enjoy direct access to Mill Pond and easy ground-level entry. There are no additional cleaning costs. Your comfort is our priority! As an added bonus, a portion of your stay supports St. Jude Children’s Research Hospital!

FamilyValueParking

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.
Flat in Windsor Locks
4.82 out of 5 average rating, 202 reviews

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

LocationValueCheckout

Guest favourite
A charming brick exterior of the retreat features multiple large windows and a welcoming front entrance. Lush green grass surrounds the property, with decorative landscaping elements visible, including flowering plants. Solar panels are situated on the roof, reflecting an eco-friendly design.
Guest house in Enfield
4.94 out of 5 average rating, 99 reviews

Close AirPort|SixFlags|Big E|Free Private Parking

Escape to Pineside Retreat in Enfield, CT—a tranquil haven blending comfort and nature. Conveniently located 20 minutes from Bradley Airport and MGM Springfield Casino, 15 minutes from Six Flags, 22 minutes from Holyoke Mall, 5 minutes from Scantic River State Park, and 10 minutes from Windsor Locks Canal State Park. Perfect for professionals or adventurers seeking relaxation in a cozy, rustic-modern retreat. Per-person pricing. Please select the correct number of guests when booking.

FamilyValueTV

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
4.92 out of 5 average rating, 108 reviews

Island Vibes

Come and enjoy a tranquil stay with an island vibe. This 3 bedroom, 2 bath home will comfortably accommodate up to 8 persons. Large kitchen and living space for everyone. Situated in a quiet suburb on the outskirts of downtown Hartford, it is 12 minutes from Bradley International Airport, 20 minutes from the Basketball Hall of Fame and Springfield Museums Quadrangle. In the region is the Connecticut Science Museum, The Mark Twain House, Wadsworth Atheneum Museum of Art, and much more.

FamilyLocationAmenities

Guest favourite
Cottage in Windsor
4.89 out of 5 average rating, 219 reviews

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.

ValueFamilyGetting around

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
4.89 out of 5 average rating, 113 reviews

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!

LocationFamilyHospitality

Guest favourite
Guest suite in East Granby
4.85 out of 5 average rating, 426 reviews

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

LocationFamilySolo travel

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
4.94 out of 5 average rating, 118 reviews

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.

FamilyLocationComfort

Top guest favourite
The charming stone cottage features a vibrant blue door and flower boxes filled with colorful plants. Lush greenery surrounds the entrance, and original brick walkways lead to the home. Sunlight filters through the trees, creating a welcoming atmosphere outside.
Guest house in Granby
4.98 out of 5 average rating, 926 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

FamilyValueAir conditioning

Guest favourite
The exterior of a charming red schoolhouse and accessory building is surrounded by vibrant foliage. A white wooden fence outlines the property, leading to a gravel pathway. The buildings feature classic architectural details, with windows framed in white and a backdrop of lush trees.
Cottage in Granby
4.86 out of 5 average rating, 257 reviews

The Little Red Schoolhouse ~ Circa 1877

This wonderful old building is listed on the National Register of Historic Places and operated as the District 9 schoolhouse until 1948. Now, this beautiful piece of history is available for you to enjoy! Located in the picturesque West Granby, Connecticut, this little schoolhouse directly abuts hundreds of acres of open space, Granby Land Trust property, and several organic farms.

LocationValueSleep quality

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.
Flat in Enfield
4.99 out of 5 average rating, 335 reviews

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.

ValueFamilyGetting around

Popular amenities for Windsor holiday rentals

KitchenWifiPoolFree 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

Top guest favourite
Tiny home in Mansfield
5 out of 5 average rating, 33 reviews

Handcrafted Timber Frame Cabin Retreat

LocationWifiCleanliness

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
4.97 out of 5 average rating, 72 reviews

By The River

LocationValueCheck-in

Top guest favourite
Home in Windsor Locks
4.96 out of 5 average rating, 50 reviews

The Hangar

LocationFamilyOutdoor spaces

Top 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
4.9 out of 5 average rating, 42 reviews

The Majestic View | Luxury Stay Golf Views

FamilyLocationComfort

Top guest favourite
The living area features comfortable blue sofas arranged around a central coffee table. A dark wood media console holds a large TV displaying the Netflix logo. A modern kitchen is visible in the background, equipped with white cabinetry and stainless-steel appliances.
Flat in Simsbury
4.89 out of 5 average rating, 44 reviews

Newly Renovated Apartment

LocationFamilyDecor

Guest favourite
Guest house in Windsor
4.97 out of 5 average rating, 39 reviews

Your New England Summer Getaway!

ValueFamilyGetting around

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.
Flat in Bloomfield
4.98 out of 5 average rating, 53 reviews

Bloomfield Bungalow

ValueLocationOutdoor spaces

Guest favourite
Flat in New Britain
4.95 out of 5 average rating, 284 reviews

Spacious Cozy Guest Suite

LocationFamilyHeating

When is the best time to visit Windsor?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price₹12,453₹13,028₹12,453₹12,932₹13,890₹9,963₹10,442₹11,495₹12,166₹12,549₹12,645₹12,645
Avg. temp-3°C-1°C3°C10°C16°C20°C24°C23°C18°C12°C6°C0°C

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