Holiday rentals in Windsor

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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
4.88 out of 5 average rating, 172 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,

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
4.85 out of 5 average rating, 187 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

Top guest favourite
An expansive view of rolling hills and distant mountains is visible through a treeline, with a foreground of manicured green grass and apple trees. The cabin's wooden structure is partially seen on the right, enhancing the connection to nature.
Cabin in Williamsburg
4.97 out of 5 average rating, 116 reviews

Mountain Retreat close to Northampton & Amherst!

Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley, and Amherst, then this cabin is perfect. Within walking distance, you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.

Top guest favourite
A cozy living room features a stone fireplace surrounded by purple walls. A wooden table sits at the center, adorned with a decorative bowl. A comfortable sofa and a wooden chair are positioned near the fireplace, complementing the warm ambiance.
Cottage in Windsor
4.9 out of 5 average rating, 203 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.

Guest favourite
Tiny home in New Marlborough
4.95 out of 5 average rating, 150 reviews

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Top guest favourite
Flat in New Britain
4.96 out of 5 average rating, 257 reviews

Spacious Cozy Guest Suite

This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

Top guest favourite
Home in West Suffield
4.97 out of 5 average rating, 121 reviews

Linny’s Lake House - with dock

Linny’s Lake House & Dock Access 🌲🌳 Charming Lakeside Home on South Pond Welcome to our newly renovated lake house tucked into a peaceful 3/4-acre wooded lot, naturally treated to keep mosquitoes and ticks to a minimum. The setting feels calm and restorative, with gentle breezes, shaded trees, and the charm of nearby tobacco fields adding to the sense of being away without being remote.

Top guest favourite
A brick patio area is seen with two rocking chairs positioned beside vibrant orange and yellow flower pots. A welcoming wreath adorns the double doors, and a pumpkin is placed on the ground, enhancing the seasonal decor.
Guest suite in East Granby
4.86 out of 5 average rating, 407 reviews

Staying at Ten Hillcrest

What I’ve always thought of as 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 with no through traffic. On your way out take a left and head towards farm and eateries or take a right and head to the city of Hartford or Springfield. Just minutes from Bradley International Airport

Top guest favourite
The exterior of a colonial barn-style apartment is shown, featuring a stone chimney and a combination of red siding and a gray roof. Lush greenery surrounds the entrance, which includes large glass windows and a welcoming door. A grassy area is visible in the foreground.
Guest house in Glastonbury
4.92 out of 5 average rating, 225 reviews

Charming Barn Apartment

Our one bedroom apartment in a colonial barn has a country feeling but is a 10 minute drive into downtown Hartford, and halfway between Boston and New York City .There are woods on one side and from the living area look out on a hillside where you can sit for a spell or spend some time on the private stone patio right outside the door. There are beaches and casinos within an hours drive.

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, 893 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!

Superhost
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
4.87 out of 5 average rating, 240 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.

Guest favourite
A spacious living area features a large L-shaped sectional sofa adorned with a cozy blanket. A wooden coffee table sits in front on a patterned area rug. Two windows allow natural light to fill the room, and a decorative mirror is mounted on the wall.
Flat in West Hartford
4.87 out of 5 average rating, 135 reviews

West Hartford Center Apartment

Spacious 1 bedroom 1 bathroom apartment with a private entrance. A 10 minute walk from Blueback square, Whole Foods Market & more. Kitchen fully furnished, high speed internet, private balcony, 86 inch smart TV, in a quiet and safe neighborhood. Washer and dryer in apartment, free driveway parking. Pets allowed

Popular amenities for Windsor holiday rentals

When is the best time to visit Windsor?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Windsor?

    Windsor has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Windsor?

    Experience the best of Windsor with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Windsor?

    Four-legged friends are welcome in Windsor. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Windsor?

    Yes! Work meets play with ease at over 50 vacation rentals in Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Windsor?

    Make yourself at home in Windsor by choosing from our most frequently booked neighborhoods. We have over 20 vacation rentals in Hayden, and over 70 vacation rentals in Windsor Locks.

  • Do house rentals in Windsor have air conditioning?

    Absolutely! We offer over 40 house rentals with air conditioning in Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Windsor have a kitchen?

    Absolutely! We offer over 40 house rentals with a kitchen in Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Windsor have wifi?

    Absolutely! We offer over 40 house rentals with wifi in Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Windsor have free parking?

    Absolutely! We offer over 40 house rentals with free parking in Windsor. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Windsor?

    Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with air conditioning, over 40 homes with a kitchen, over 40 homes with free parking, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Windsor

  • Total holiday rentals

    Explore 70 holiday rentals in Windsor

  • Nightly prices starting at

    Windsor holiday rentals start at € 26 per night before taxes and fees

  • Verified guest reviews

    Over 1,850 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    70 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