Choose from 17 vacation rentals located in Roxbury, Connecticut. Top filters in Roxbury include Air conditioner, Internet / Wifi, and Kitchen / Kitchenette. Prices range from $80 to $1,246 per night. Our most popular vacation rental types near Roxbury are Hotel and RV.

Top vacation rentals in Roxbury

Moosehorn High Ceiling Colonial, Best Neighborhood - Actors, Writers, Artists
5.0
Outstanding(10 Reviews)
House
 in Roxbury
100% ROXBURY! PoshPadsCT "MOOSEHORN" 2HrsNYC, Mint 6-BR, Pool, Ski, BBQ, Bikes
12 guests · 6 bedrooms · 5 baths
Garden · Pool · Pets allowed

Business stays, family stays, couples stay, getaway vacation, and rental in Roxbury at 100% ROXBURY! PoshPadsCT "MOOSEHORN" 2HrsNYC, Mint 6-BR, Pool, Ski, BBQ, Bikes for $1,024 for your next trip.

$$$$
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Mint Antique Reproduction 6-Bedroom 
Please see the VIDEO in the navigation bar
4.8
Outstanding(4 Reviews)
House
 in Roxbury
100% ROXBURY! PoshPadsCT "SENTRY HILL" 1.5Hrs NYC,Mint 6BR, Pool, Ski, Bike, BBQ
12 guests · 6 bedrooms · 4 baths
Garden · Pool · Pets allowed

Experience vacation in Roxbury with our House, 100% ROXBURY! PoshPadsCT "SENTRY HILL" 1.5Hrs NYC,Mint 6BR, Pool, Ski, Bike, BBQ. Enjoy amenities such as Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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4 Bedrooms, 4 Bath Heated Pool, Best Roxbury Location, Mint Restoration
4.7
Outstanding(8 Reviews)
House
 in Roxbury
BEST TOWN ROXBURY! PoshPadsCT "247 PAINTER" 1.5Hrs NYC, Mint, Ski, Fires, BBQ
10 guests · 4 bedrooms · 4 baths
Garden · Pool · Pets allowed

Experience the best of Roxbury with this House available for $986. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Front entrance with gate for privacy
4.7
Outstanding(32 Reviews)
House
 in Roxbury
Litchfield County Four Season Country Paradise
12 guests · 5 bedrooms · 5 baths
Garden · Pool · Pets allowed

Looking for a House in Roxbury, this House for $945 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

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Search by amenity

Vacation rentals with air conditioning in Roxbury

Painter Ridge Farm House - Best Roxbury Celebrity, Artist, Writer Neighborhood
House
 in Roxbury
ROXBURY BEST LOCATION! PoshPadsCT"PAINTER RIDGE"Mint3BR,Pool,BBQ,Bike,1.5HrsNYC
8 guests · 3 bedrooms · 3 baths
Garden · Pool · Pets allowed

When traveling to Roxbury, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $843 per night.

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Spectacular Pool House with salt Water Heated Poo, Gas BBQ, Gardens, Fire Pit
House
 in Roxbury
BEST TOWN ROXBURY!1.5Hrs NYC PoshPadsCT "TOPHET POOL BARN" Ski,Pool,BBQ,Magical!
5 guests · 1 bedroom · 1 bath
Garden · Pool · Pets allowed

Soak up the beauty of Roxbury in our House, BEST TOWN ROXBURY!1.5Hrs NYC PoshPadsCT "TOPHET POOL BARN" Ski,Pool,BBQ,Magical!. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.

$$$$
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Painter Hilltop Mint 4 Bedroom Home, Views, Nearby Farms, Walk & Bike Ride
5.0
Outstanding(1 Review)
House
 in Roxbury
BEST LOCATION! PoshPadsCT"PAINTER HILL4BR" Hot Tub Spa, BBQ, Ski,Hike,1.5HrsNYC
10 guests · 4 bedrooms · 3 baths
Garden · Pets allowed · Kitchen / Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Roxbury at BEST LOCATION! PoshPadsCT"PAINTER HILL4BR" Hot Tub Spa, BBQ, Ski,Hike,1.5HrsNYC for $830 for your next trip.

$$$$
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Exterior
Farm Stay
 in Roxbury
Twilight Dreams Farm
6 guests · 3 bedrooms · 2 baths
Ski in / Ski out · Garden · Kitchen / Kitchenette

This inviting Farm Stay in Roxbury can fit your needs for many types of vacations, at $459 per night.

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Roxbury

Roxbury travel guide

Let us help you plan your perfect Roxbury vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Roxbury, and more.

Frequently asked questions

What is the price range for rentals in Roxbury?

Vacation rentals in Roxbury have a price range between $80-$1,246. The average price for rentals in Roxbury is $767 per night.

What are the top things to do in Roxbury, CT?

Roxbury, CT is a great place to explore and discover new things. Here are four of the top things to do in Roxbury:

  • Visit the Roxbury Land Trust for outdoor activities like hiking and mountain biking.
  • Take a tour of the historic Roxbury Iron Works Museum.
  • Explore the nature trails at the White Memorial Conservation Center.
  • Visit the Roxbury Wine Trail for some of the best local wines.

These are just a few of the great things to do in Roxbury, CT. Whether you’re looking for outdoor activities, a bit of history, or a chance to sample some of the local wines, Roxbury has something for everyone!

What are the most popular vacation rental amenities in Roxbury, CT?

The most popular vacation rental amenities in Roxbury, CT include:

  • Modern furnishings
  • Fully-equipped kitchen
  • High-speed internet access
  • Laundry facilities
  • Outdoor recreation areas

These amenities provide guests with a comfortable and enjoyable stay while visiting Roxbury, CT. Many rental properties also offer additional amenities such as a hot tub, private pool, or game room, depending on the size and type of rental.

Where is Roxbury, CT?

Roxbury, Connecticut is a town located in Litchfield County. It is bordered by the towns of Bridgewater, Washington, Woodbury, and Southbury. It is home to the Roxbury Land Trust, which works to preserve the town's natural beauty and resources.

What are the best neighborhoods to visit in Roxbury, CT?

The best neighborhoods to visit in Roxbury, CT are:

  • Dodgingtown
  • Shepaug
  • Booth Hill

Each of these neighborhoods offer something unique, from the historic Dodgingtown, to the quaint Shepaug, to the bustling Booth Hill. There's something for everyone in Roxbury, CT!

What are the popular shopping destinations in Roxbury, CT?

The popular shopping destinations in Roxbury, CT are:

  • The Roxbury Mall
  • The Roxbury Marketplace
  • Roxbury Antiques & Collectibles

Is Roxbury, CT safe to travel to?

Roxbury, CT is generally considered safe to travel to. Here are some tips to ensure a safe and enjoyable visit:

  • Avoid walking alone late at night.
  • Be aware of your surroundings at all times.
  • Keep your valuables secure and out of sight.

What is the culture like in Roxbury, CT?

Roxbury, CT is a small, rural town located in the northwest corner of the state. The culture is heavily influenced by the town’s rural nature and its rural roots.

  • There is a strong sense of community and a focus on family values.
  • Outdoor activities are popular, including hunting, fishing, hiking, and camping.
  • Roxbury is known for its local artisans, including painters, woodworkers, and potters.
  • The town is home to a vibrant music scene, with live music performances in local restaurants and bars.
  • Roxbury is a great place to relax and enjoy the beauty of nature, with plenty of open spaces and beautiful views.

Where can I find affordable accommodation in Roxbury, CT?

Roxbury, CT has a variety of affordable accommodation options. Here are four of the best:

  • The Roxbury Inn: A cozy bed and breakfast located in the heart of the town.
  • The Roxbury Motel: A family-friendly motel with comfortable rooms and amenities.
  • Roxbury Inn & Suites: An affordable hotel with modern amenities and convenient access to local attractions.
  • Roxbury Lodge: A rustic lodge nestled in the woods with a variety of activities for all ages.

How can I get around in Roxbury, CT?

You can get around in Roxbury, CT by:

  • Walking
  • Biking
  • Driving

Additionally, you can access the bus services provided by the Connecticut Department of Transportation. You can also take advantage of the rideshare services offered by Uber and Lyft.

What are the must-visit tourist attractions in Roxbury, CT?

Roxbury, CT is a great place to visit, with many attractions to explore. Here are some of the must-visit tourist attractions in Roxbury, CT:

  • The Roxbury Land Trust
  • The Hodge Preserve
  • The Shepaug River
  • The Hopkins Vineyard

The Roxbury Land Trust is a great place to explore the outdoors, with miles of trails to explore. The Hodge Preserve offers scenic views of the countryside, and the Shepaug River is a great spot for fishing and tubing. Finally, the Hopkins Vineyard is a great place to enjoy a glass of wine while taking in the views.

What do I need to know before visiting Roxbury, CT?

Before visiting Roxbury, CT, it is important to know the following:

  • The town is located in Litchfield County.
  • The town has a population of approximately 2,100.
  • The town is known for its rural beauty and community life.

Roxbury is home to a variety of outdoor attractions, including the Shepaug River, which is a popular spot for fishing and swimming. There are also several hiking trails, parks, and historic sites in the area. Additionally, there are several restaurants, cafes, and shops in the town.

What are the most popular vacation rental amenities in Roxbury?

  • Air conditioner
  • Internet / Wifi
  • Kitchen / Kitchenette

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