Holiday houses in South Windsor

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!

Value · Location · View

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,

Location · Value · Accuracy

Hike & Stay | 3 BR w/ Fenced Yard

This pet-friendly cozy 3-bedroom, 1-bath home is tucked into a private, quiet neighborhood in Manchester, offering space to unwind while staying close to everything. Whether you’re visiting family, exploring the outdoors, or just need a comfortable home base, this spot keeps things simple and relaxed. Large private deck and separate gazebo perfect for morning coffee or evening wind-down. Fully fenced yard. Ten minutes from Hartford, CT and 30 minutes from Bradley International Airport.

Location · Family · Quiet

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).

Family · Value · Sleep quality

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.

Location · Value · Bathroom

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!

Location · Value · Getting around

Family Retreat Near Hartford – Year-Round Getaway

Make this home your fall retreat. With 5 bedrooms, 3 baths, a full kitchen, and a quiet office with fast Wi-Fi, there’s space for family and friends to relax or work comfortably. Just 10 minutes to downtown Hartford, UConn football, the Big E, other popular fairs, local orchards, pumpkin patches, and scenic leaf-peeping trails. Laundry, parking, and family-friendly touches included. No parties or pets. Perfect for autumn getaways, work trips, or extended stays.

Family · Location · Backyard

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.

Family · Value · Bathroom

5 Bd 2.5 Bth Home Away From Home

The whole group will enjoy easy access to everything from this centrally located home. Visit the many restaurants, mall and other shopping areas while staying in a peaceful serine environment right outside a major city. Close proximity to highways (I-91 I-291 and I-84) and Bradley international Airport is within 16mi of the house. Equiped with washer/dryer and dedicated office space, it is good for professionals and a family long-term or short-term stay.

Location · Value · Hospitality

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.

Value · Location · Decor

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.

Family · Location · Wi-Fi

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.

Family · Value · Hospitality