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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Top Guest favourite

A contemporary lakefront home is surrounded by tall trees, with a spacious deck offering views of Middle Bolton Lake. A fire pit is situated on a stone patio, surrounded by Adirondack chairs. The lush green yard leads to the water's edge, enhancing the natural ambiance.

Home in Vernon

Luxe Bolton Lake

Stay at Luxe Bolton Lake and feel like you are a million miles from home! The Luxe features a BEAUTIFUL WATERFRONT, 3 bedrooms/3 full bathrooms and a year-round outdoor JACUZZI Also included: gorgeous primary bedroom suite, artistic furnishings, cozy FIREPLACE, coffee bar, complimentary snacks, speedy WiFi, large deck, fire pit, KAYAKS, board games, and much more. The Luxe is perfectly suited for families and guests of all ages, so come stay at Luxe and make memories that will last a lifetime!

FamilyValueBeach

4.99 out of 5 average rating, 186 reviews

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,

ValueLocationTV

4.86 out of 5 average rating, 198 reviews

Guest favourite

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

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.

FamilyLocationDecor

4.93 out of 5 average rating, 244 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).

FamilyValueCheckout

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.

LocationValueSleep quality

4.89 out of 5 average rating, 222 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!

LocationValueHospitality

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.

ValueFamilyOutdoor spaces

4.92 out of 5 average rating, 111 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

You will be close to everything when you stay at this centrally-located home. Located just 10 minutes from downtown Hartford where there are many attractions, sporting events, concerts, museums and restaurants. The property abuts Fairway Mini Golf & Batting Cages serving ice cream and burgers. You can relax on the back porch or around the fire pit in the spacious back yard. Enjoy the beautiful updated kitchen with views of the back yard.

FamilyLocationBackyard

4.86 out of 5 average rating, 79 reviews

Guest favourite

Apartment in Manchester

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.

LocationFamilyCleanliness

4.96 out of 5 average rating, 160 reviews

Superhost

A welcoming entryway features a cheerful red front door and a staircase leading to the upper level. Comfortable seating in red and gray tones invites guests to relax. Decorative elements include a small side table with a clock and an arrangement of flowers.

Home in Manchester

4 BDR Cape | 15 mins to Hartford | 25 mins to BDL

I cannot wait to host you at this beautiful Cape! You will be welcomed with modern vibes and coziness. Kitchen is fully equipped. All 4 bedrooms have queen beds and black out curtains. Full bathroom comes with shower/soaking tub combo and superb water pressure. House is equipped with a office desk, chair and reliable WiFi making it suitable for a home office. The smart TV in the living room is perfect for a movie night.

FamilyValueWalkability

4.8 out of 5 average rating, 173 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.

ValueFamilyDecor

4.94 out of 5 average rating, 123 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.

FamilyLocationCleanliness

4.99 out of 5 average rating, 344 reviews