Roxbury vacation rentals

We found 295 vacation rentals — enter your dates for availability

Welcome to Roxbury, where enchanting parks, serene lakes, and friendly neighborhoods come together to create the perfect getaway for nature lovers and families alike. Explore the breathtaking trails of Steep Rock Preserve, unwind at the picturesque Candlewood Lake, or enjoy thrilling rides at Quassy Amusement Park. With a diverse selection of cozy homes, stylish apartments, and charming cottages, you’ll find the ideal base for creating unforgettable memories, all while enjoying the comfort and convenience of a vacation rental.

Holiday rentals with weekly discounts - Roxbury

Showing deals for:Sep 25 - Oct 2

Image gallery for Nature & Luxury @Lavender Lake Est (Kosher optional)

Pool
10 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

Nature & Luxury @Lavender Lake Est (Kosher optional)

Roxbury

9% off
Price is $1,248
$8,735 for 7 nights
All fees included
Nature & Luxury @Lavender Lake Est (Kosher optional)

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Roxbury

Why visit Roxbury

  • Outdoor Adventures: Roxbury is perfect for nature lovers, offering stunning parks, serene lakes, and inviting urban green spaces.
  • Charming Neighborhoods: Explore friendly neighborhoods filled with rich history and picturesque scenery.
  • Family-Friendly Activities: The area boasts a variety of attractions suitable for all ages, ensuring fun for the whole family.
  • Local Culture: Enjoy delightful shopping destinations and cultural experiences that reflect the essence of Roxbury.
  • Variety of Accommodations: Choose from cozy homes, stylish apartments, and charming cottages to suit every traveler's needs.

Popular types of accommodation in Roxbury

Planning your getaway to Roxbury? The next step is selecting the perfect place to stay. Discover a variety of vacation rental options, including cozy private homes, stylish apartments, and charming cottages. Whether you're looking for a spacious bedroom home or a pet-friendly retreat, Roxbury has something to suit every traveler's needs. Explore your options and make your trip unforgettable.

  • Houses: The top choice for travelers in Roxbury, these homes offer spacious accommodations perfect for families, friends, or couples seeking a home-away-from-home experience.
  • Apartments: A popular second option, apartments provide convenient and comfortable living spaces ideal for those who want a more urban feel during their stay.
  • Cottages: These quaint and charming options are perfect for a cozy getaway, making them a favored third choice among visitors.
  • Cabins: Offering a rustic atmosphere, cabins are a beloved fourth option for nature enthusiasts looking to relax in serenity.
  • Villas: As the fifth choice, villas provide luxurious accommodations, perfect for those wanting an upscale experience in Roxbury.**

Top attractions near Roxbury

Roxbury, Connecticut is perfect for outdoor enthusiasts and those seeking romantic getaways. Visitors can explore stunning national and state parks, serene lakes, and inviting urban parks. The area's attractions cater to a variety of interests, offering opportunities for cultural experiences and family-friendly activities. Whether you're looking to relax in nature or enjoy local attractions, Roxbury is an ideal destination for your vacation.

  • Candlewood Lake: Nestled 8 miles from Roxbury, Candlewood Lake offers a serene escape with stunning scenery and romantic vibes. Enjoy outdoor activities like swimming, kayaking, or simply relaxing on the beach, surrounded by natural beauty.
  • Quassy Amusement Park: Also 8 miles away, Quassy Amusement Park is perfect for family adventures. Experience thrilling rides, classic games, and water attractions, all set in a picturesque outdoor environment.
  • Steep Rock Preserve: Just 5 miles from Roxbury, Steep Rock Preserve is a tranquil haven for families and nature lovers. Explore scenic trails, relax by the river, and immerse yourself in the area's rich cultural history.

Things to do recommended for couples

For a romantic getaway in Roxbury, explore the scenic hiking trails at the Roxbury Land Trust, or enjoy a cozy picnic at the picturesque Lake Lillinonah. Don't miss a wine tasting at a local vineyard, perfect for a delightful afternoon together.

Things to do recommended for families

Families visiting Roxbury, Connecticut can explore the beautiful nature trails at the Roxbury Land Trust, enjoy hands-on activities at the nearby Steep Rock Association, and visit local farms for fun seasonal events. Don't miss the charming small-town atmosphere and family-friendly restaurants to complete your experience.

Things to do recommended for groups

Explore the scenic beauty of Roxbury by hiking the trails at the Roxbury Land Trust or enjoy a group wine tasting at the nearby Haight-Brown Vineyard. Don't miss the charming local shops and eateries for a taste of New England hospitality.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, family, or pets, or if you're considering longer stays, be sure to use the appropriate filters to prioritize your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Roxbury with a group: Think about how many bedrooms you'll require, as well as any features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Roxbury with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with providing age-appropriate amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Roxbury: For many families, a trip isn't truly fulfilling without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties offer amenities like feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Roxbury: If you're seeking vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Roxbury

Roxbury, Connecticut, offers a charming blend of outdoor adventures and picturesque scenery, perfect for a romantic getaway or family vacation. Explore the friendly neighborhoods, rich history, and beautiful landscapes that define this quaint town. Nearby attractions include delightful shopping destinations and historical sites, ensuring a memorable experience. Whether you're looking to unwind in nature or indulge in local culture, Roxbury is the perfect base for your Connecticut adventures.

  • Waterbury: Located 14 miles from Roxbury, Waterbury is a vibrant city that offers a rich blend of family-friendly activities and outdoor adventures. Visitors can enjoy attractions like the local amusement park and waterpark, perfect for creating memorable experiences. The city is also home to event conference venues, making it a hub for gatherings and entertainment. Whether you're exploring educational institutions or spending a day in the park, Waterbury provides a lively urban atmosphere with plenty of options for relaxation and fun.
  • Danbury: Just 13 miles from Roxbury, Danbury is known for its stunning scenery and outdoor experiences, making it ideal for a romantic getaway. The city features a variety of shopping centers and malls, offering ample retail therapy. Nature enthusiasts can explore nearby lakes and scenic areas, while the event conference venue adds a touch of sophistication for those looking to attend or host events. Danbury’s blend of urban convenience and natural beauty provides a delightful escape for travelers.
  • New Milford: A mere 6 miles away from Roxbury, New Milford is a charming city that emphasizes outdoor activities and picturesque landscapes. Visitors can stroll through local markets and recreational areas, soaking in the serene environment. With attractions like a national state park and a beautiful beach nearby, New Milford is perfect for those seeking romance and tranquility. The city's scenic charm, combined with its welcoming atmosphere, makes it an ideal destination for a peaceful retreat.

Best time to go to Roxbury

If you're planning a trip to Roxbury, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from May to July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.2°F (-2.1°C)Light RainMostly SunnySlightly LowSlightly Low
February29.8°F (-1.2°C)Light RainMostly CloudyAverageAverage
March37.2°F (2.9°C)Light RainMostly SunnyAverageSlightly Low
April48.4°F (9.1°C)Light RainMostly SunnyAverageSlightly Low
May59.0°F (15.0°C)Light RainMostly SunnySlightly HighAverage
June67.3°F (19.6°C)Light RainMostly SunnySlightly HighSlightly High
July73.9°F (23.3°C)Light RainMostly SunnySlightly HighSlightly High
August72.1°F (22.3°C)Light RainMostly SunnyAverageSlightly High
September65.1°F (18.4°C)Light RainMostly SunnyAverageAverage
October54.3°F (12.4°C)Light RainMostly SunnyAverageAverage
November42.3°F (5.7°C)Light RainMostly SunnySlightly LowAverage
December34.3°F (1.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that meets your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a convenient area for you to plan new trips, refine your existing plans, or manage your bookings. Your saved or reserved properties are neatly categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Roxbury getaway

Experience the unique character of Roxbury with a stay in a vacation home rental. There's no shortage of things to see and do in the area.Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in Roxbury

Are you looking for things to do while you're in town? Venture out of your cozy vacation rental and check out everything that makes Roxbury a fun place to get away. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • The Christmas Shop (7.5 mi / 12.1 km)
  • Quassy Amusement Park (8.4 mi / 13.6 km)
  • Hopkins Vineyard (10.5 mi / 16.9 km)
  • Thunder Ridge Ski Resort (14.4 mi / 23.2 km)
  • Richter Park Golf Course (14.7 mi / 23.6 km)
  • DiGrazia Winery (6.9 mi / 11 km)

Exploring the natural landscape of Roxbury

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

  • Steep Rock Preserve (4.6 mi / 7.4 km)
  • Bellamy-Ferriday House and Garden (7.8 mi / 12.5 km)
  • Candlewood Lake (8.5 mi / 13.7 km)
  • Lake Waramaug (10.2 mi / 16.4 km)
  • Bear Mountain Reservation (10.8 mi / 17.4 km)
  • Bantam Lake (11.2 mi / 18 km)

Traveling to and around Roxbury

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 10.3 mi (16.6 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 15.7 mi (25.2 km) away.

Frequently asked questions

What is the best area to stay in Roxbury, Connecticut, United States of America when booking a vacation rental?
When considering a vacation rental in Roxbury, Connecticut, the charming neighborhoods of Roxbury Center and Southbury are excellent options. Roxbury Center exudes a quaint, small-town vibe with its picturesque landscapes and historic architecture, making it a delightful place to explore. Nearby, you can enjoy the scenic beauty of the Roxbury Land Trust, which features serene walking trails and abundant opportunities for outdoor activities.

In Southbury, just a short drive away, you can visit the beautiful Lake Quassapaug, great for swimming, fishing, or simply relaxing by the water. The area also offers a variety of dining options and local shops that add to its appeal. While the exact number of vacation rental properties can vary, both neighborhoods provide a range of accommodations that suit different preferences and budgets.
How much does it cost to rent a vacation home in Roxbury?
Prices for vacation rentals in Roxbury 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 Roxbury 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 Roxbury vacation house rentals?
You can find great discounts on house rentals in Roxbury 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.
Where are the best Roxbury ski resort rentals?
For ski resort rentals near Roxbury, travelers can consider the nearby area of New Hartford, which is home to the Ski Sundown resort. This ski area is just a short drive away and offers a variety of slopes for different skill levels. In New Hartford, you can find cozy cabins and chalets that provide convenient access to the ski resort. Many of these properties come equipped with amenities such as fireplaces, full kitchens, and outdoor spaces for relaxing after a day on the slopes.

Additionally, the charming town of Litchfield, located a bit further but still within reach of Ski Sundown, offers a selection of vacation rentals, including historic homes and modern lodges. These accommodations often feature amenities like spacious living areas, hot tubs, and proximity to local dining options, making them ideal for families or groups seeking comfort and convenience.

The surrounding areas also present opportunities for winter activities beyond skiing, such as snowshoeing and cross-country skiing, with beautiful trails in the nearby state parks.
What is the most popular type of vacation rental accomodation in Roxbury?
In Roxbury, vacation houses are the most common type of rental, with about 14 available throughout the area. These houses typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups seeking a cozy feel. Many properties also include outdoor spaces, such as decks or gardens, where guests can relax and enjoy the surrounding natural beauty. Additionally, there are several cabins and apartments, which offer alternative accommodations for those looking for a different experience.
Are there any family house rentals in Roxbury?
In Roxbury, Connecticut, there are some available family-friendly house rentals that cater to groups seeking a comfortable stay. This picturesque town is known for its charming rural atmosphere and beautiful landscapes. Many of the homes in the area offer spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and explore.

Visitors will find that Roxbury is surrounded by scenic nature, with nearby attractions such as Lake Waramaug State Park, superb for picnicking and water activities. Other local highlights include hiking trails and serene views, making it an ideal spot for families looking to enjoy the outdoors together.
Can I rent a vacation home with a pool or hot tub in Roxbury?
In Roxbury, Connecticut, there are approximately 10 vacation homes available for rent that feature pools or hot tubs, making it a great choice for travelers seeking relaxation. This picturesque town offers a serene environment, with properties often situated on spacious lots that provide privacy and beautiful views of the surrounding landscape. Many of these rentals come with amenities such as private pools, inviting hot tubs, outdoor patios, and fully equipped kitchens, superb for family gatherings or quiet retreats.
Can I find long-stay vacation rentals in Roxbury?
A long-stay vacation rental in Roxbury is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Roxbury?
In Roxbury, Connecticut, there are several pet-friendly house rentals available, offering a welcoming environment for travelers with pets. Visitors can expect amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, providing comfort for both humans and their furry companions. These rentals often come with outdoor spaces where pets can play and explore, making them an excellent choice for families or groups traveling with pets.

The surrounding area features beautiful landscapes, with nearby parks and outdoor spaces that are superb for walking and enjoying nature with pets. While Roxbury itself is a charming small town, it is also conveniently located near larger towns where additional amenities and services can be found. See all pet-friendly rentals in Roxbury.
Are there any remote work vacation rentals in Roxbury?
In Roxbury, Connecticut, there are several remote work-friendly vacation rentals available, with around 16 options to choose from. This picturesque town offers a peaceful setting ideal for productivity, surrounded by beautiful natural landscapes. Many properties come equipped with essential amenities for remote work, such as reliable Wi-Fi, comfortable workspaces, and in some cases, even computer monitors and printers available for use.

Travelers can expect a mix of cozy cabins and spacious homes, often featuring serene outdoor spaces to take breaks or enjoy the fresh air. The area is also known for its charming rural character, making it a great choice for those looking to balance work and relaxation. Additionally, the nearby parks and scenic trails provide opportunities for outdoor activities during downtime, ensuring a refreshing work-life balance. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Roxbury vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Roxbury with parking available—perfect for families or travelers 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 Roxbury?
In Roxbury, popular vacation rental amenities include spacious decks or patios, great for enjoying the serene surroundings. Many rentals come equipped with fully functional kitchens, allowing guests to prepare their own meals. A cozy fireplace is often featured, providing warmth and ambiance during cooler evenings. Additionally, many properties include a blender for those who enjoy making smoothies or cocktails. For travelers with furry companions, pet-friendly options are available, making it easy to bring pets along for the stay.
When is the best time to visit Roxbury for a vacation rental?
The most popular time to visit Roxbury is during the peak season from May to July, with June standing out as a particularly vibrant month. This is when the charming town comes alive, welcoming travelers eager to experience its beautiful countryside and outdoor activities. With temperatures typically ranging from the mid-50s to the low 80s Fahrenheit, the weather is great for hiking, biking, and enjoying the serene landscapes that surround this quaint Connecticut town.

During the summer, visitors can partake in various local events and festivals, fostering a sense of community and offering opportunities to mingle with fellow travelers. The lush greenery and blooming flowers make this season ideal for picturesque walks through Roxbury, where you can explore historical sites and enjoy the scenic beauty of the area.

If you're looking for a more budget-friendly option, consider visiting in December. While the winter months may be quieter, Roxbury transforms into a cozy wonderland, great for those who appreciate a peaceful atmosphere. This time of year is excellent for enjoying winter activities, such as snowshoeing or simply relaxing by a warm fireplace in your rental.
How early should I book a Roxbury vacation rental?
Book your Roxbury vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Roxbury, Connecticut, United States of America?
In Roxbury, visitors can enjoy a blend of natural beauty and cultural attractions. The Roxbury Land Trust offers numerous scenic trails for hiking and nature walks, allowing travelers to immerse themselves in the picturesque landscapes of rural Connecticut. The historic Roxbury Museum showcases the town's rich history and heritage, making it a worthwhile stop for those interested in local culture.

Nearby, the scenic Lake Lillinonah provides opportunities for outdoor activities such as fishing and kayaking, while the charming town center features quaint shops and local eateries that reflect the area's small-town charm.
Can I change or cancel my Roxbury home rental booking on Vrbo?
To find Roxbury vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Roxbury vacation 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

More Vacation Ideas