Holiday houses in South Windsor

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Top-rated holiday rentals in South 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, 184 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 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
4.93 out of 5 average rating, 238 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.

Guest favourite
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.
Apartment in East Windsor
4.86 out of 5 average rating, 120 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!

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
4.83 out of 5 average rating, 198 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

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
4.91 out of 5 average rating, 103 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.

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, 101 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!

Top 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, 109 reviews

Quiet Comfy Getaway 3 BDR home

Our newly renovated 3-bedroom home offers a comfortable and convenient stay. Perfectly located with easy access to the grocery stores, strip malls, hospitals, and parks, it's an ideal base for your trip. Our home comes with ample parking, pristine kitchen and bathrooms, mini coffee bar, cooking utensils, free WiFi, and a washer/dryer. Stay productive with our dedicated workspace and unwind in our spacious bedrooms. Book now for a home away from home experience!

Guest favourite
Apartment in Manchester
4.96 out of 5 average rating, 141 reviews

Peaceful Pet-Friendly Retreat Near Hartford and MA

Welcome to your home away from home located steps away from downtown Manchester CT! ✔ Private entrance
✔ 1 comfortable bedroom & full bathroom
✔ Fast Wi-Fi for work and entertainment
✔ In-unit washer & dryer
✔ Complimentary coffee
✔ Pet-friendly accommodations
✔ Backyard access
✔ Quiet, residential setting Conveniently located close enough to major events but in a quaint downtown area making it prefect for short or long term stays.

Top Guest favourite
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 Hartford
4.99 out of 5 average rating, 797 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 and several universities. 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.

Top 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
4.88 out of 5 average rating, 288 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 😊.

Guest favourite
Home in Tolland
4.94 out of 5 average rating, 283 reviews

The Carriage House

Private 1BR carriage house apartment in Tolland, CT, 5 min to I-84 and 15 min to UConn. Separate entrance with no shared spaces. Includes full kitchen, Wi-Fi, laundry, parking, and Level 2 EV charging. Sleeps up to 4 with optional queen mattress. Quiet wooded setting. Self check-in. No pets, smoking, or parties. Some light noise possible from upstairs unit.

Top Guest favourite
The kitchen features dark wood cabinetry and a spacious island with bar seating for two. A small dining setup is placed on the island, complemented by decorative plants on the countertop. Natural light fills the room through a large window, creating a bright space.
Apartment in Ellington
4.98 out of 5 average rating, 110 reviews

Cozy Apartment in Ellington

Cozy 2nd floor apartment in residential area, located between Hartford and UCONN. Close access to interstate 84 and 91. A small town feeling with access to local good eats and shopping. For those nature lovers we are located close to Shenipsit Lake with walking, hiking and fishing. Numerous parks, playgrounds and trails nearby.

Popular amenities for South Windsor holiday rentals