Simsbury holiday rentals

We found 212 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:18 Dec - 25 Dec

Property grounds
Property grounds
Interior
Exterior
Wonderful
(12 reviews)

Cozy Lake Garda Home-Baby/Kid/Pet Friendly

Burlington

8% off
AU$3,846
for 7 nights, 1 home
AU$549 per night
includes taxes & fees
Cozy Lake Garda Home-Baby/Kid/Pet Friendly
Private kitchen
Dining
Interior
Terrace/patio
Exceptional
(5 reviews)

Modern Family Retreat w/ Office & Fast WiFi

East Hartford

7% off
AU$5,993
for 7 nights, 1 home
AU$856 per night
includes taxes & fees
Modern Family Retreat w/ Office & Fast WiFi
Private kitchen
Exterior
Living area
Room
Exceptional
(20 reviews)

Charming 2-bedroom house centrally located in Bristol

Bristol

8% off
AU$1,816
for 7 nights, 1 home
AU$259 per night
includes taxes & fees
Charming 2-bedroom house centrally located in Bristol
Living area
Private kitchen
Dining
Interior
Exceptional
(11 reviews)

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

Windsor Locks

16% off
AU$3,450
for 7 nights, 1 home
AU$493 per night
includes taxes & fees
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Games room
Private kitchen
Property grounds
Outdoor dining
Exceptional
(78 reviews)

Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table

Suffield

8% off
AU$2,660
for 7 nights, 1 apartment
AU$380 per night
includes taxes & fees
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table
Interior
Terrace/patio
Room
Dining
Exceptional
(10 reviews)

WeHa Penthouse w/ Private Deck

West Hartford

8% off
AU$1,730
for 7 nights, 1 home
AU$247 per night
includes taxes & fees
WeHa Penthouse w/ Private Deck

  • 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

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:

  • Flamig Farm (2.6 mi / 4.2 km)
  • Talcott Mountain State Park (3.2 mi / 5.1 km)
  • Ski Sundown (6.6 mi / 10.5 km)
  • East Hartford Golf Course (12.8 mi / 20.6 km)
  • Cabela's (12.9 mi / 20.8 km)
  • Connecticut Valley Winery (13.1 mi / 21.1 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:

  • Sperry Park (4.3 mi / 6.9 km)
  • Farmington River (4.8 mi / 7.7 km)
  • Northwest Park (6.1 mi / 9.8 km)
  • Elizabeth Park (8.5 mi / 13.6 km)
  • West Hartford Reservoir (9.4 mi / 15.1 km)
  • Bushnell Park (10.3 mi / 16.6 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 Springfield Union Station (ZSF), which is 19.6 mi (31.6 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 is the charming centre of Simsbury itself. This picturesque neighbourhood offers a delightful blend of historical charm and modern convenience. Here, you can explore the stunning Simsbury Town Forest, which features a network of beautiful trails great for hiking and nature walks. Additionally, the iconic Old Drake Hill Flower Bridge, adorned with vibrant blooms, is a lovely spot for a leisurely stroll and makes for fantastic photographs.Another appealing area is the nearby Tariffville, which is known for its scenic views and proximity to the Farmington River. This neighbourhood is great for those who enjoy outdoor activities such as kayaking or fishing. The Tariffville Gorge is a popular attraction, providing a serene environment for picnics and relaxation.In terms of holiday rentals, Simsbury offers a diverse selection of properties, ranging from quaint cottages to spacious family homes. This variety ensures that visitors can find accommodation that suits their preferences and needs, all while being surrounded by the area's natural beauty and rich history.
What is the most popular type of holiday rental accomodation in Simsbury?
In Simsbury, 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 private outdoor spaces for relaxation. Many properties are situated in quiet neighbourhoods, providing a peaceful retreat while still being conveniently located near local attractions such as the historic Simsbury Centre and the picturesque Farmington River.
Are there any family house rentals in Simsbury?
In Simsbury, Connecticut, there are several family-friendly house rentals available, making it an ideal spot for those looking to enjoy a getaway with loved ones. The town features charming neighbourhoods with easy access to parks and recreational activities. Many of these homes offer spacious living areas, fully equipped kitchens, and outdoor spaces where children can play safely.Visitors can also explore local attractions such as the picturesque Simsbury Farms, which includes a swimming pool, golf course, and hiking trails. The nearby Talcott Mountain State Park provides beautiful scenery and opportunities for family-friendly hikes.
Are there pet-friendly house rentals in Simsbury?
In Simsbury, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these holiday homes feature spacious layouts, modern kitchens, and comfortable living areas, ensuring a relaxing stay. Some properties also include outdoor spaces such as gardens or patios, great for pets to enjoy.The town is known for its picturesque landscapes and outdoor activities, making it an excellent choice for pet owners. Nearby, you can explore the scenic Simsbury Land Trust trails, which offer beautiful walking routes where you can take your pets for a stroll. Additionally, the picturesque Farmington River provides opportunities for leisurely walks and enjoying nature with your four-legged friends.
Are there any remote work holiday rentals in Simsbury?
In Simsbury, Connecticut, there are several holiday rentals that cater to remote work needs. Many of these properties come equipped with high-speed Wi-Fi, dedicated workspaces or desks, and some even feature inviting living areas that make it easier to balance work and relaxation. The amenities provided ensure a comfortable environment for productivity, including access to free internet and quiet surroundings.Simsbury itself is a picturesque town with a rich history and beautiful landscapes, superb for those looking to unwind after a day of work. Nearby, you can explore local parks, hiking trails, and historical sites, which add to the appeal of working remotely in this charming area. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Simsbury?
In Simsbury, popular rental amenities include fireplaces, which add a warm and inviting touch to accommodations, especially during the colder months. Many properties also feature fitness facilities, suiting those who wish to maintain their workout routines while away. Expect kitchens in most rentals, allowing guests the convenience of preparing their own meals. Onsite parking is another common amenity, making it easy for visitors to explore the area without concern for vehicle safety. Additionally, accessible parking is available for those with mobility needs, ensuring a welcoming stay for everyone.
When is the best time to visit Simsbury for a holiday rental?
July marks the peak season for visiting Simsbury, Connecticut, where vibrant summer days invite travellers to explore the scenic beauty and rich history of the area. This month is particularly popular for families and outdoor enthusiasts, as the warm temperatures, typically ranging from 20 to 30 degrees Celsius, create an ideal setting for hiking, biking, and enjoying local festivals.During the summer months from July to September, Simsbury bustles with activity. Visitors can partake in various outdoor events, including concerts in the park and farmers' markets, all while appreciating the stunning landscapes that define this charming New England town. The lush greenery and picturesque views make it a lovely time to engage in leisurely sightseeing or simply relax in a holiday rental.For those seeking a more budget-friendly option, November offers a quieter experience with fewer crowds. This month is great for enjoying the crisp autumn air and witnessing the beauty of fall foliage without the hustle and bustle of peak season. You can embrace the tranquillity of Simsbury's parks and take in the serene atmosphere, all while finding great value in your accommodation choices.Ultimately, the best time to visit Simsbury depends on your travel preferences.
What are the top attractions in Simsbury?
In Simsbury, visitors can explore a variety of attractions that highlight the area's natural beauty and historical significance. One of the main draws is the Simsbury Historical Society, where guests can learn about the town's rich heritage. The picturesque Talcott Mountain State Park offers stunning views and hiking trails, superb for outdoor enthusiasts. Additionally, the iconic Heublein Tower, perched atop Talcott Mountain, provides panoramic vistas of the Farmington Valley.Simsbury Farms, with its golf course and recreational facilities, is another popular spot for families and sports lovers. The local arts scene can be enjoyed at the Simsbury Centre, which hosts various events and festivals throughout the year. For those interested in a scenic stroll, the Farmington River Trail offers a beautiful pathway for walking, biking, and enjoying the serene surroundings.
Are all fees included in the Simsbury 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 Simsbury holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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 Simsbury holiday homes?
You can find great discounts on holiday homes in Simsbury 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 Simsbury holiday home booking on Stayz?
To find Simsbury 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 Simsbury?
A long-stay holiday home 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 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 Simsbury holiday home?
Book your Simsbury 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 Simsbury?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Simsbury 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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