Photo by Patricia Mari

Sherman holiday rentals

We found 146 holiday rentals — enter your dates for availability
Discover a selection of 9 homes and other holiday rentals in Sherman that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as parking and a TV. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

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Choose a holiday rental for your Sherman getaway

Learn about the unique charm of Sherman with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Sherman

Are you hoping to discover attractions to see during your stay? Venture out of your cosy holiday rental and experience everything that makes Sherman a one-of-a-kind holiday spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Thunder Ridge Ski Resort (6.5 mi / 10.4 km)
  • Hopkins Vineyard (11.5 mi / 18.4 km)
  • The Christmas Shop (15.4 mi / 24.8 km)
  • Quassy Amusement Park (18.3 mi / 29.4 km)
  • Putnam County Golf Course (18.9 mi / 30.4 km)
  • Mohawk Mountain Ski Area (20.2 mi / 32.5 km)

Exploring the natural features in Sherman

Whether you're looking for adventure or just want to take in the scenery, Sherman is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Candlewood Lake (6.3 mi / 10.1 km)
  • Whaley Lake (8.7 mi / 13.9 km)
  • Bear Mountain Reservation (9.3 mi / 14.9 km)
  • Lake Waramaug State Park (10.8 mi / 17.4 km)
  • Lake Waramaug (10.9 mi / 17.5 km)
  • Tymor Park (11.7 mi / 18.8 km)

How to get to and around Sherman

Fly into Danbury, CT (DXR-Danbury Municipal), the closest airport, located 14.2 mi (22.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Oxford, CT (OXC-Waterbury - Oxford), which is 19.8 mi (31.9 km) away.

Frequently asked questions

What is the best area to stay in Sherman when booking a holiday rental?
When considering a holiday rental in Sherman, Connecticut, a popular area to stay in is the charming neighbourhood surrounding the town centre. This area boasts a lovely blend of historic character and natural beauty, making it an ideal spot for visitors. With a selection of approximately 50 holiday rental properties available, you'll find a variety of options that cater to different preferences and budgets.Staying near the town centre allows easy access to local attractions such as the picturesque Lake Candlewood, which is superb for boating, fishing, or simply relaxing by the water. Additionally, the nearby Sherman Historical Society offers insights into the town's rich heritage, showcasing various exhibits and events throughout the year.Another delightful aspect of this neighbourhood is its proximity to the scenic hiking trails in the surrounding woods, providing ample opportunities for outdoor enthusiasts to explore the natural landscape.
What is the most popular type of holiday rental accomodation in Sherman?
In Sherman, holiday houses and cottages are the most popular types of holiday rentals, with several available throughout the area. These accommodations typically offer a comfortable and homey atmosphere, with amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces for relaxation. Many properties are situated near the scenic Candlewood Lake, providing a superb backdrop for outdoor activities like boating and fishing. Additionally, these rentals are often found in tranquil neighbourhoods, making them ideal for families or groups looking to escape the hustle and bustle.
Are there any family house rentals in Sherman?
In Sherman, Connecticut, there are several family-friendly house rentals available. This charming area offers a variety of properties suitable for larger groups, with many featuring spacious living areas, multiple bedrooms, and outdoor spaces for children to enjoy. Families can expect amenities such as fully equipped kitchens, where home-cooked meals can be easily prepared, and comfortable lounges for relaxation after a day of activities.The locale is known for its scenic beauty, including nearby Candlewood Lake, which is superb for swimming, fishing, or picnicking. Additionally, visitors can explore the surrounding parks and nature reserves, providing ample opportunities for hiking and outdoor adventures.
Can I rent a holiday home with a pool or hot tub in Sherman?
In Sherman, Connecticut, there are several holiday homes available for rent that feature pools and hot tubs. This picturesque town, located in the scenic landscapes of the Candlewood Lake area, provides a tranquil setting for relaxation and outdoor activities. Travellers can expect amenities such as private pools, hot tubs, spacious outdoor areas for entertaining, and fully equipped kitchens ideal for family gatherings. Many properties also offer comfortable living spaces and easy access to local attractions, ensuring a delightful stay.
Are there pet-friendly house rentals in Sherman?
In Sherman, Connecticut, there are several pet-friendly house rentals available, offering a great opportunity for travellers with pets. Many of these properties come equipped with amenities such as spacious backyards, allowing for plenty of room for pets to play, as well as well-appointed kitchens and comfortable living areas for relaxation after a day of exploring.The town is situated near scenic areas, including the beautiful Lake Candlewood, which provides opportunities for outdoor activities such as hiking and boating. This can be a delightful experience for pet owners, as the lake area features walking trails and picnic spots that are pet-friendly.
Are there any remote work holiday rentals in Sherman?
In Sherman, Connecticut, there are several remote work holiday rentals available, making it a great choice for those looking to combine work and leisure. Properties in the area typically offer amenities such as free Wi-Fi, dedicated workspaces with desks and chairs, and sometimes additional features like computer monitors to facilitate a comfortable remote work environment.Beyond the work-friendly setups, Sherman is known for its picturesque landscapes, providing a tranquil setting for breaks. Nearby, you can explore scenic spots such as Lake Candlewood, superb for outdoor activities like hiking and boating, ensuring a balanced experience of productivity and relaxation during your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Sherman?
In Sherman, holiday rentals commonly feature a variety of amenities that enhance the comfort and convenience of guests. Most properties come equipped with kitchens, allowing travellers to prepare their own meals, along with coffee and tea makers for that essential morning brew. Onsite parking is typically available, making it easy for visitors to explore the surrounding areas. Many rentals also include dining areas, providing a welcoming space to enjoy meals together. Some properties may offer additional amenities such as blenders for those who enjoy smoothies or cooking.
When is the best time to visit Sherman for a holiday rental?
The best time to book a holiday rental in Sherman is during the peak summer months of June to August, particularly in July when the weather is at its finest. This vibrant period attracts families and outdoor enthusiasts alike, offering a lot of activities including hiking, boating, and exploring the stunning natural beauty of Candlewood Lake. The warm temperatures, typically ranging from 20 to 30 degrees Celsius, create the great environment for enjoying the outdoors.July is especially popular for its lively option, as visitors flock to local events and festivals. You'll find a welcoming community eager to share the charm of Sherman, making it an ideal time for those seeking both adventure and relaxation. The abundance of outdoor spaces allows for easy exploration, whether you're picnicking by the lake or wandering through the picturesque town centre.If you're looking for a more budget-friendly option, consider visiting in December. While this is the low season, it presents a unique opportunity to experience Sherman's tranquil winter landscape and holiday festivities. The town's serene charm during this time offers a peaceful retreat, great for cozy getaways.Ultimately, your choice will depend on whether you prefer the lively summer activities or the quiet, reflective atmosphere of winter.
What are the top attractions in Sherman?
In Sherman, Connecticut, visitors can enjoy a serene escape with a variety of attractions that highlight the area's natural beauty. One of the main draws is Lake Candlewood, where guests can partake in activities such as swimming, fishing, and boating, all while taking in the picturesque waterfront views. The surrounding parks, like the scenic Squantz Pond State Park, offer hiking trails and picnic spots, making it an ideal location for outdoor enthusiasts.The town also boasts charming local shops and eateries, particularly around the historic town centre, which showcases New England architecture and provides a quaint atmosphere for leisurely strolls. For those interested in local history, the Sherman Historical Society offers insights into the town's past and its development over the years.
Are all fees included in the Sherman 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 Sherman holiday homes with parking?
Stayz offers a wide selection of holiday homes in Sherman 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 Sherman holiday homes?
You can find great discounts on holiday homes in Sherman 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 Sherman holiday home booking on Stayz?
To find Sherman 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 Sherman?
A long-stay holiday home in Sherman 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 Sherman holiday home?
Book your Sherman 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 Sherman?
Prices for holiday homes in Sherman 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 Sherman 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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