South Windsor holiday rentals

We found 245 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in South Windsor that are perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. At the end of the day, you'll be able to choose a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – South Windsor

Showing deals for:8 Jan - 15 Jan

Dining
Interior
Room
Living area
Exceptional
(19 reviews)

John Hollister home on the farm

Glastonbury

16% off
AU$3,745
for 7 nights, 1 home
AU$535 per night
includes taxes & fees
John Hollister home on the farm
Stay in The Red Onion Room. (Queen bed)
Private kitchen
Interior
Living area
Exceptional
(25 reviews)

Charming Historic Owl House in Old Wethersfield

Old Wethersfield

8% off
AU$5,957
for 7 nights, 1 home
AU$851 per night
includes taxes & fees
Charming Historic Owl House in Old Wethersfield
Interior
Private kitchen
Living area
Room
Exceptional
(12 reviews)

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Windsor Locks

15% off
AU$2,559
for 7 nights, 1 home
AU$366 per night
includes taxes & fees
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Living area
Dining
Private kitchen
Interior
Exceptional
(6 reviews)

Modern Family Retreat w/ Office & Fast WiFi

East Hartford

7% off
AU$6,112
for 7 nights, 1 home
AU$873 per night
includes taxes & fees
Modern Family Retreat w/ Office & Fast WiFi
Interior
Living area
Private kitchen
Room
Wonderful
(28 reviews)

New!Quaint & Convenient Hideaway: Great Location

East Hartford

7% off
AU$1,996
for 7 nights, 1 home
AU$285 per night
includes taxes & fees
New!Quaint & Convenient Hideaway: Great Location
Interior
Interior
Dining
Living area
Exceptional
(29 reviews)

Your Tranquil Escape Inside an Island‑Inspired Home

Windsor

7% off
AU$2,509
for 7 nights, 1 home
AU$358 per night
includes taxes & fees
Your Tranquil Escape Inside an Island‑Inspired Home

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Take in the natural beauty of South Windsor

Learn about the unique charm of South Windsor with a stay in a holiday home rental. This city's shopping, golfing and restaurants draw many visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around South Windsor

Are you searching for things to do in the city? Venture out of your holiday home and check out everything that makes South Windsor a fun spot to go on holiday. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • East Hartford Golf Course (4.2 mi / 6.8 km)
  • Cabela's (6.9 mi / 11.1 km)
  • Wintonbury Hills Golf Course (9.7 mi / 15.5 km)
  • Sonny's Place (10.9 mi / 17.5 km)
  • Talcott Mountain State Park (11.4 mi / 18.4 km)
  • Six Flags New England (13.4 mi / 21.5 km)

Exploring the natural features in South Windsor

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, South Windsor is a great place to spend some time outside. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Wickham Park (4.3 mi / 7 km)
  • Riverside Park (6.9 mi / 11.1 km)
  • Northwest Park (7.4 mi / 11.9 km)
  • Bolton Notch State Park (7.5 mi / 12 km)
  • Connecticut River (7.5 mi / 12.1 km)
  • Mortensen Riverfront Plaza (7.6 mi / 12.2 km)

Transport to and around South Windsor

The nearest airport is in Hartford, CT (BDL-Bradley Intl.), located 8.1 mi (13.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Springfield Union Station (ZSF), which is 17.8 mi (28.6 km) away.

Frequently asked questions

What is the best area to stay in South Windsor when booking a holiday rental?
When considering a holiday rental in South Windsor, Connecticut, an excellent area to stay in is the neighbourhood near the picturesque parks and recreational facilities that the town is known for. This region boasts a variety of properties, suiting different tastes and budgets, making it a practical choice for visitors.A highlight of this area is the beautiful Wickham Park, which offers expansive green spaces, walking trails, and lovely gardens, great for leisurely strolls or picnics. Additionally, the nearby South Windsor Historical Society provides a glimpse into the local history, with engaging exhibits that celebrate the town's heritage.Staying in this neighbourhood allows easy access to both nature and cultural attractions, making it ideal for families or those seeking a tranquil retreat.
What is the most popular type of holiday rental accomodation in South Windsor?
In South Windsor, holiday houses are the predominant type of holiday rental, with several available throughout the area. These homes typically offer spacious living arrangements, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces such as gardens or patios, ideal for families or groups looking for a comfortable stay. South Windsor provides a friendly suburban atmosphere, making these rental options great for those seeking a home-away-from-home experience while enjoying the local parks and nearby attractions.
Are there any remote work holiday rentals in South Windsor?
In South Windsor, Connecticut, there are several remote work holiday rentals available, making it a great choice for those looking to balance work and leisure. Many of these properties come equipped with reliable internet access, ensuring that guests can stay connected and productive during their stay.The town itself offers a pleasant suburban environment, with parks and walking trails nearby, providing opportunities for breaks and relaxation. Visitors can expect amenities such as dedicated workspaces, comfortable living areas, and fully equipped kitchens, great for self-catering during longer stays. Additionally, South Windsor's proximity to Hartford allows for easy access to more urban attractions, should you wish to explore the vibrant cultural scene in the nearby city. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in South Windsor?
In South Windsor, popular rental amenities include outdoor spaces such as decks and patios, offering guests a pleasant area to relax or entertain. Onsite parking is commonly available, providing convenience for those travelling with vehicles. Additionally, many rentals feature WiFi, ensuring that guests can stay connected during their stay.
When is the best time to visit South Windsor for a holiday rental?
The peak season for visiting South Windsor is from May to July, with July being the most popular month. This vibrant period attracts families and outdoor enthusiasts eager to enjoy the warm weather, lush parks, and local events. With temperatures often reaching the mid-20s Celsius, visitors can partake in activities such as hiking, cycling, and picnicking in the scenic surroundings.During these summer months, the town comes alive with various festivals and community gatherings, making it a fantastic time to immerse yourself in the local culture. The pleasant climate allows for comfortable outdoor activities, whether you're exploring the beautiful parks, visiting nearby attractions, or simply enjoying a leisurely stroll through the charming streets.For those seeking a more budget-friendly experience, consider planning your visit in November. While this month is quieter, it offers a unique opportunity to enjoy the crisp autumn air and the changing colours of the foliage. This tranquil time allows for reflective walks in the parks and the chance to experience South Windsor's local charm without the hustle and bustle of the peak season.Ultimately, your ideal time to visit South Windsor will depend on your desire for lively summer experiences or a peaceful autumn retreat.
What are the top attractions in South Windsor?
In South Windsor, visitors can enjoy a variety of attractions that showcase the town's charm and natural beauty. The Connecticut River is a significant draw, offering picturesque views and opportunities for outdoor activities like kayaking and fishing. Nearby, the lush landscapes of the Nevers Park provide walking trails and picnic areas, superb for family outings.For those interested in local history, the South Windsor Historical Society offers insights into the town's past, and the charming South Windsor Town Green often hosts community events and seasonal festivals. Additionally, the nearby Wapping Park features sports facilities and scenic walking paths, making it a great spot for recreation.Shopping enthusiasts can explore the local shops and eateries along Sullivan Avenue, where a variety of cafes and restaurants cater to different tastes.
Are all fees included in the South Windsor holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any South Windsor holiday homes with parking?
Stayz offers a wide selection of holiday homes in South Windsor with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for South Windsor holiday homes?
You can find great discounts on holiday homes in South Windsor on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my South Windsor holiday home booking on Stayz?
To find South Windsor holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in South Windsor?
A long-stay holiday home in South Windsor is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a South Windsor holiday home?
Book your South Windsor holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in South Windsor?
Prices for holiday homes in South Windsor vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in South Windsor to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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