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Vacation rentals in South Windsor

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Top-rated vacation rentals in South Windsor

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

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Top guest favorite
The exterior of a newly renovated schoolhouse is depicted, showcasing a welcoming entrance with a red door. Surrounding greenery includes well-maintained lawns and established trees. A carriage house is visible on the left, complementing the charming architecture of the main house.
Home in Collinsville
4.96 out of 5 average rating, 117 reviews

Nature Lovers Retreat-Wine Vineyards Skiing nearby

Sleeps 6! Newly renovated 1910 schoolhouse. You'll love 2-3 bdr, clean, bright well appointed home. Volume ceilings, and a well stocked kitchen for long stays. Walk to nearby historic downtown Collinsville, where you'll find antique stores, restaurants and beautiful New England scenery. The CT wine trail and Brignole Vinyards nearby, where you will find food trucks and live music. Walk or cycle the Farmington River Trail. You will also find hiking, fishing, skiing, SUP , canoeing kayak rentals

Guest favorite
A private outdoor area features a spacious swimming pool with a connected spa, surrounded by greenery. Two decorative lion statues flank the pool entrance. Lounge chairs and a gazebo provide additional relaxation options under a sunny sky dotted with clouds.
Home in Columbia
4.91 out of 5 average rating, 112 reviews

Breathtaking home with unforgettable views & pool!

This perfect peaceful and private home on 5 acres is great for unwinding & relaxing whether it is enjoying the day by the incredible pool/spa or star gazing at night. far from the noise and pollution of city life. You can spend a weekend or a week away from work life because you deserve it. Close to Foxwoods casino and Mohegan sun casino, super Walmart and other stores. please let us know before booking more than 4 people whether it is just for the day or night or both. no loud music no parties

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,

Guest favorite
A comfortable sleeping area features a dark tufted headboard and a soft, neatly arranged bedding with multiple pillows. A lamp is positioned on a bedside table, while a floor lamp provides additional light. A floral wall art piece adds a subtle touch above the bed.
Home in Manchester
4.94 out of 5 average rating, 229 reviews

Paradise On The Hill Luxury Apartment.

Enjoy your own special and separated section of this beautiful, modern colonial home. This spacious home includes central air, an oversize living room with a comfortable Queen Size sectional sleeper sofa, oversize Master Bedroom and very large, newly renovated bathroom with spa like jets. His and hers closets. Beautiful fully stocked kitchenette, 2 large screen Smart TVs, 55 inch in living room, 42 inch in bedroom, Free WiFi, dining for 6, all for the comfort and convenience of our guests.

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
4.85 out of 5 average rating, 186 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

Superhost
A charming kitchenette is showcased with colorful cabinetry and floral wallpaper. Pendant lights hang above the counter, illuminating the space. A dining area with two chairs and a small table is visible, while decor items add character to the walls and shelves.
Guesthouse in Vernon
4.87 out of 5 average rating, 156 reviews

Cozy private one bedroom guest apt suite

Centrally located, just minutes from I84, 20 min to Uconn, 15 min to capital of Hartford, 1 hour drive to Cts famous casinos, 30 min to MGM Springfield, enjoy local dining close by. Private entrance guest suite with parking for one vehicle at your door. Private bedroom with double bed and pull out sofa in living room area, workspace, smart tv, internet ready, kitchenette with fridge, microwave, 2 burner cooktop, and coffee maker, snacks and refreshments, linens, some toiletries available

Top guest favorite
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, 200 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.

Top guest favorite
A bright bedroom features a queen size bed with light linens and decorative pillows. A small desk and chair are positioned beside the bed. A closet offers hanging space, and a floral artwork adorns the wall, adding a touch of color to the space.
Guest suite in Vernon
4.98 out of 5 average rating, 214 reviews

Laura's Loft and Gallery, private suite

Unique and spacious loft with private entrance, two bedrooms with space to sleep 4, full bath with tub shower, and plenty of room to relax. Kitchen with mini fridge, toaster oven, microwave, hot plate. Pleasant living area opening to 2nd floor deck. WiFi plus ethernet, great remote work space. Quiet and private, only common area shared with us is first floor entry into breezeway. Free parking on premises. Full coffee setup, plus homemade scones in seasonal flavors for your enjoyment!

Guest favorite
The living room features a cozy arrangement of green couches around a coffee table. A stone fireplace serves as the focal point, surrounded by wooden paneling. Bright sunlight enters through large windows, illuminating the space and highlighting nearby decor.
Cabin in Coventry
4.88 out of 5 average rating, 168 reviews

Lakefront - King - W&D - Fire Pit - Kayaks - Stand Up Paddleboards

Indulge in lakeside luxury at The Lake View Cottage, offering exclusive beach access & amazing views to picturesque Coventry Lake. ● 360 Mbps Wi-Fi | 50” Smart HD TV | Washer & Dryer | Indoor Fireplace ● 2x Kayaks | 2x Stand Up Paddle Boards | Beach Toys ● Record Player w/ a 100+ Vinyl Collection | Board Games ● Sunroom | Patio w/ Gas Grill | Full Kitchen | Coffee (Keurig) Drive to: UCONN (10 Mins) | Hartford (20 Mins) | Boston (1 Hour) | NYC (2 Hours)

Guest favorite
A spacious living area is furnished with a gray sectional sofa, accented with colorful throw pillows. A wooden coffee table is placed in front, on a soft area rug. Two large windows allow natural light to brighten the room, complemented by ceiling fans and tasteful decor.
Loft in Tolland
4.96 out of 5 average rating, 324 reviews

Cozy studio loft

Escape to a peaceful wooded retreat in our cozy studio loft apartment, tucked away from the road and surrounded by nature. Large windows fill the space with natural light, and wildlife is often spotted nearby. Perfect for remote work, a relaxing getaway, or a short stay. Located just minutes from the University of Connecticut and close to antique shops, scenic countryside, and Stafford Motor Speedway.

Top guest favorite
The exterior of a historic brick house is showcased, featuring a rounded turret and a welcoming front porch. Lush greenery and colorful flower beds surround the entry stairs, which lead to the front door. A small garden area adds to the inviting atmosphere of the home.
Loft in Frog Hollow
4.99 out of 5 average rating, 762 reviews

Loft - Queen Anne Row House in a historic district

Hosted by Judy and Greg, our home is close to art, culture, live theater, and restaurants. Our home is also close to major insurance companies, the state capitol and state of Connecticut offices. You’ll love the cozy 3rd floor loft. We also offer off street parking. Garage space is also available as an option. Our home is a perfect destination for couples, solo adventurers, and business travelers.

Guest favorite
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
4.86 out of 5 average rating, 247 reviews

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 a stress-free experience 😊.

Popular amenities for South Windsor vacation rentals