Simsbury holiday lettings

We found 195 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Simsbury to find one that's perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for spending time at your holiday home, including Wi-Fi and parking. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Simsbury

Showing deals for:21 Nov - 28 Nov

Image gallery for Lake Congamond Cozy Stylish Comfortable House

Interior
10 out of 10 rating
Exceptional
(6 reviews)

Lake Congamond Cozy Stylish Comfortable House

Suffield, CT

7% off
Price is £1,686
£241 nightly
Includes taxes & fees
Lake Congamond Cozy Stylish Comfortable House

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Find out more about Simsbury

Find out more about Simsbury

Why visit Simsbury

  • Outdoor Adventures: Enjoy a variety of activities in Simsbury's urban parks and scenic surroundings, perfect for nature enthusiasts.
  • Rich Heritage: Discover historic houses and learn about the town's fascinating past through its cultural experiences.
  • Charming Neighbourhoods: Stroll through the picturesque Simsbury Centre, where history beautifully intertwines with modern amenities.
  • Family-Friendly Atmosphere: Simsbury is ideal for family getaways, offering engaging activities for all ages.
  • Cozy Accommodations: Choose from an array of delightful holiday rentals, ensuring a comfortable stay in this enchanting town.

Popular types of accommodation in Simsbury

You've chosen the charming town of Simsbury for your holiday, and now it’s time to find the perfect place to stay. Explore a variety of options, from houses and delightful cottages to cosy apartments and well-appointed condos. With our selection of Simsbury holiday rentals, you’re sure to discover a comfortable base for your adventures in this picturesque destination.

  • Houses: The top choice for visitors to Simsbury, offering spacious and comfortable settings ideal for families, friends, or couples.
  • Cottages: A delightful option for a quaint and homely experience, perfect for those seeking charm and relaxation.
  • Apartments: A convenient and modern option, these rentals provide all the amenities for a hassle-free stay in the heart of Simsbury.
  • Cabins: For a rustic escape, cabins offer a unique retreat surrounded by nature, ideal for outdoor enthusiasts.
  • Chalets: These picturesque lodgings provide a cosy atmosphere, combining comfort with a touch of alpine charm.**

Top attractions near Simsbury

Simsbury is ideal for outdoor, romantic, and family getaways, boasting an array of attractions such as urban parks, historic houses, and colleges. Visitors can enjoy a mix of outdoor activities and cultural experiences, making it a delightful destination for those seeking adventure or a leisurely stroll through history. Whether you're exploring the picturesque surroundings or delving into the local heritage, Simsbury offers something for everyone.

  • Connecticut Convention Center: A modern venue for events and conferences, located 6.8km from Simsbury. Experience a bustling atmosphere ideal for business networking and professional gatherings.
  • University of Hartford: Just 5.0km away, this historic university exudes cultural vibrancy with its stunning architecture and engaging art programmes, perfect for soaking in the local educational heritage.
  • Mark Twain House & Museum: Located 6.2km from Simsbury, this charming historic house invites you to explore the life of the famed author, featuring captivating exhibits and beautiful gardens.

Things to do recommended for couples

For a romantic getaway in Simsbury, enjoy a concert at the SS&C SummerWind Performing Arts Center, just 1.9km away. Experience the thrill of skiing at Ski Sundown, 4.3km off, or unwind with a delightful wine tasting at Lost Acres Vineyard, 5.0km away, perfect for couples.

Things to do recommended for families

For a delightful family experience in Simsbury, visit the XL Center for thrilling sports events, enjoy nature at Satan's Kingdom State Recreation Area, or embark on an adventure at Nomads Adventure Quest, all within a short drive from town.

Things to do recommended for groups

Experience the vibrant culture at Xfinity Theatre, only 6.2km from Simsbury. For outdoor enthusiasts, Wintonbury Hills Golf Course offers fantastic sports vibes just 1.9km away. Don’t miss a visit to Rosedale Farms & Vineyards for a delightful local shopping experience.

What do I need to keep in mind when booking a vacation in 'Simsbury

If you’re travelling with a group, family, pets, or planning an extended stay, it’s important to refine your search according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Simsbury with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor space for socialising with your group. Luckily, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Simsbury with young kids: Travelling with young children can indeed present its challenges. It’s important to prioritise their comfort and safety, alongside ensuring access to suitable amenities like a private swimming pool. Additionally, considering your location in relation to family-friendly attractions is advisable.
  • Taking your pets with you to Simsbury: For many, a family holiday wouldn't feel right without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels completely at home.
  • Planning for a long term stay visiting Simsbury: If you're in search of holiday rentals offering discounts for month-long stays, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Simsbury

Simsbury, Connecticut, offers a delightful blend of outdoor adventures and charming neighbourhoods, perfect for families and couples alike. Explore the vibrant Simsbury Centre, where history meets modernity, or venture into the scenic surroundings for thrilling activities. The friendly atmosphere and picturesque landscapes of western Simsbury make it an ideal base to uncover the area's rich heritage and enjoy quality time with loved ones. Don't miss the enchanting experiences waiting just around the corner!

  • Windsor Locks: Situated 5.0km from Simsbury, Windsor Locks offers a delightful blend of family-friendly outdoor activities and entertainment. Visitors can enjoy a range of attractions, including amusement parks and an arena entertainment facility, making it an ideal spot for a fun-filled day out. Explore local landmarks such as a historic college university and a popular theme park, ensuring a memorable experience for all ages. The town's accessibility and variety of activities make it a convenient choice for a quick excursion.
  • Windsor: Also located 5.0km from Simsbury, Windsor is perfect for those seeking adventure and outdoor experiences. This vibrant city features ski fields and venues for music concerts, catering to both thrill-seekers and those looking to relax. Visitors can enjoy the scenic beauty of local lakes and beaches, providing a perfect backdrop for family outings. With its charming atmosphere, Windsor promises a refreshing escape into nature just a short drive away.
  • West Hartford: Just 5.6km from Simsbury, West Hartford is a bustling city that seamlessly blends family activities with business-themed experiences. Known for its excellent shopping areas and golf courses, it's an excellent location for both leisure and productivity. Enjoy visits to historic college universities and various event venues that host numerous activities throughout the year. West Hartford's vibrant urban environment, coupled with its family-friendly offerings, makes it a worthwhile stop on your journey.

Best time to go to Simsbury

If you're planning a trip to Simsbury, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January27.3°F (-2.6°C)Light RainMostly SunnyAverageSlightly Low
February28.9°F (-1.7°C)Light RainMostly CloudyAverageAverage
March36.5°F (2.5°C)Light RainMostly SunnyAverageSlightly Low
April47.7°F (8.7°C)Light RainMostly SunnySlightly HighSlightly Low
May58.6°F (14.8°C)Light RainMostly SunnyAverageAverage
June66.7°F (19.3°C)Light RainMostly SunnyAverageSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighSlightly High
August71.4°F (21.9°C)Light RainMostly SunnyAverageSlightly High
September64.4°F (18.0°C)Light RainMostly SunnySlightly HighAverage
October53.4°F (11.9°C)Light RainMostly SunnySlightly LowAverage
November41.7°F (5.4°C)Light RainMostly SunnySlightly LowAverage
December33.6°F (0.9°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider adjusting your travel dates, as prices can fluctuate significantly. Moreover, opting for a longer stay can often result in substantial savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to refine your search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new journeys, pick up from where you last stopped, or manage and review your travel arrangements. You can easily access the properties you’ve saved and booked, now neatly categorised under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The historical area of Simsbury awaits your stay

Enjoy the history and other features of Simsbury. This romantic city is known for its restaurants, hiking and forests. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Simsbury

Are you hoping to discover things to do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Simsbury has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Six Flags New England (15.4 mi / 24.7 km)
  • Flamig Farm (2.6 mi / 4.2 km)
  • Wintonbury Hills Golf Course (3.2 mi / 5.1 km)
  • Talcott Mountain State Park (3.2 mi / 5.1 km)
  • Gillette Ridge Golf Course (5.6 mi / 8.9 km)
  • Wampanoag Country Club (6.1 mi / 9.7 km)

Exploring the natural features in Simsbury

Whether you're looking for adventure or just want to take in the scenery, Simsbury is a great place to spend some time outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Farmington River (4.8 mi / 7.7 km)
  • Northwest Park (6.1 mi / 9.8 km)
  • Enders State Forest (6.4 mi / 10.3 km)
  • Satan's Kingdom State Recreation Area (7.5 mi / 12.1 km)
  • Elizabeth Park (8.5 mi / 13.6 km)
  • Keney Park (8.7 mi / 14.1 km)

Travelling to and around Simsbury

Fly into Hartford, CT (BDL-Bradley Intl.), the closest airport, located 7.6 mi (12.3 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Westfield, MA (BAF-Barnes Municipal), which is 20.8 mi (33.5 km) away.

Frequently asked questions

What is the best area to stay in Simsbury when booking a holiday rental?
When considering a holiday rental in Simsbury, Connecticut, a popular area to stay in is the picturesque downtown district. This charming neighbourhood offers a delightful blend of local shops, cafes, and restaurants, making it a vibrant hub for visitors. Staying here places you within easy reach of the Simsbury Town Forest, which is superb for hiking and enjoying the beautiful natural scenery. Additionally, the nearby Simsbury Historical Society provides a fascinating glimpse into the area's rich history.

Another appealing neighbourhood is the West Simsbury area, known for its tranquil residential charm and proximity to the stunning Talcott Mountain State Park. This park boasts breathtaking views and a variety of outdoor activities, making it an excellent choice for nature enthusiasts. The West Simsbury area also offers a selection of holiday rentals, suiting different preferences and budgets.
How much does it cost to rent a holiday home in Simsbury?
Prices for holiday rentals in Simsbury 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Simsbury to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Simsbury holiday house rentals?
You can find great discounts on house rentals in Simsbury on Vrbo, 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.
What is the most popular type of holiday rental accomodation in Simsbury?
In Simsbury, holiday houses are the most popular type of rental accommodation, with several available throughout the area. These properties typically offer spacious interiors, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many of these homes also feature outdoor spaces, such as patios or gardens, where guests can relax and enjoy the picturesque surroundings.
Are there any family house rentals in Simsbury?
In Simsbury, Connecticut, there are several family-friendly house rentals available, making it a splendid choice for those travelling with children. The neighbourhoods around the town centre and near Talcott Mountain State Park offer spacious homes that often feature inviting living areas, fully equipped kitchens, and ample outdoor space for kids to enjoy.

These properties typically include modern amenities such as Wi-Fi and laundry facilities, which make family stays more convenient. Visitors can explore the scenic beauty of the nearby Farmington River or take advantage of local parks that provide playgrounds and picnic areas, superb for family outings.
Can I find long-stay holiday rentals in Simsbury?
A long-stay holiday rental in Simsbury 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any remote work holiday rentals in Simsbury?
In Simsbury, Connecticut, there are several remote work holiday rentals available, suiting those who need a productive environment away from home. Many of these properties are equipped with essential amenities such as high-speed Wi-Fi, dedicated desks, comfortable desk chairs, and office spaces, ensuring a conducive atmosphere for working remotely. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Simsbury holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Simsbury 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 on Vrbo 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.
What are popular rental amenities in Simsbury?
In Simsbury, popular rental amenities typically include fully equipped kitchens, which are essential for guests looking to prepare their own meals. Many properties feature coffee makers, cookware, dishware, and utensils, making it convenient for travellers to enjoy home-cooked meals. Additionally, some rentals come with dishwashers for easy clean-up after dining. For those seeking a compact option, there are also rentals with kitchenettes available, providing a smaller cooking space while still offering the basics for meal preparation.
When is the best time to visit Simsbury for a holiday rental?
The best time to visit Simsbury for a holiday rental is during the peak season, which runs from July to September. This summer period entices travellers with its vibrant community events, lush landscapes, and an array of outdoor activities. Visitors can enjoy the picturesque Farmington River, great for kayaking or leisurely hikes, all while basking in the warm sunshine.

July stands out as the most popular month, drawing travellers. With temperatures typically ranging from 20 to 30 degrees Celsius, it's ideal for exploring local parks, cycling along scenic trails, or simply enjoying a picnic with breathtaking views of the Connecticut countryside. The charming town also hosts various festivals and fairs during this time, creating a lively atmosphere that enhances the overall experience.

For those seeking a more budget-friendly option, consider visiting in November. This month offers a unique charm with the onset of fall, as the leaves transition into a stunning palette of orange and gold. While the tourist crowds have thinned, you can still enjoy the serene beauty of Simsbury's historic sites and outdoor spaces, making it a peaceful retreat.
How early should I book a Simsbury holiday rental?
Book your Simsbury holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Simsbury?
In Simsbury, visitors can enjoy a variety of attractions that showcase the town's natural beauty and historical significance. The Simsbury Historic District offers charming historic architecture and sites like the Simsbury Free Library and the old Drake Hill Flower Bridge, a picturesque spot for photos.

For those interested in outdoor activities, Talcott Mountain State Park is a popular destination, featuring hiking trails with stunning views of the Farmington Valley and the iconic Heublein Tower. Additionally, the Farmington River is superb for kayaking and fishing, providing a serene escape into nature.
Can I change or cancel my Simsbury home rental booking on Vrbo?
To find Simsbury holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Simsbury holiday rental prices shown on Vrbo?
Vrbo 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.

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