Photo by Jennifer Brokaw

Roxbury holiday homes

We found 266 holiday rentals — enter your dates for availability

Discover a selection of 16 homes and other holiday rentals in Roxbury that are perfect for your trip. Holiday rentals provide the best amenities for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • 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

Find the perfect holiday rental for your Roxbury getaway

Learn about the unique charm of Roxbury with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Roxbury

Are you looking for things to do in the city? Venture out of your cosy holiday rental and check out everything that Roxbury has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Haight-Brown Vineyard (14.6 mi / 23.4 km)
  • Richter Park Golf Course (14.7 mi / 23.6 km)

Exploring the natural landscape of Roxbury

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Roxbury is a great place to spend some time outside. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Steep Rock Preserve (4.6 mi / 7.4 km)
  • Lake Lillinonah (5.2 mi / 8.4 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)
  • Lake Zoar (10.9 mi / 17.5 km)

Travelling to and around Roxbury

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 10.3 mi (16.6 km) from the city centre. 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 most popular type of holiday home accommodation in Roxbury?
Houses are the most popular kind of holiday home in Roxbury, according to our data. Even if you have a different idea about what you want, Bookabach has holiday homes in loads of sizes and shapes. Filter our options to find your perfect pad.
How much does it cost to rent a holiday home in Roxbury?
Property type, length of stay and time of year are some factors that can determine the price of a holiday home. Simply add your dates of travel to find your dream escape. From comfy cabins to expansive villas, all Bookabach holiday homes offer terrific value.
How much does it cost to rent a beach house in Roxbury?
When you travel and the style and size of the property will help determine the cost of your beachside stay. Click on your Roxbury travel dates to view your available options on Bookabach. Can’t live without a hot tub, or maybe a private pool? Use our filters to pick the amenities and features you want.
Are there pet-friendly holiday homes in Roxbury?
Happily, yes. Choose from 17 stays that roll out the welcome mat in Roxbury on Bookabach. Our cuddly best friends need a getaway too, so simply use our search function for pet-friendly holiday homes to find a perfect pad where Fido can get in on the family fun.
Can I rent a house with a pool in Roxbury?
Add a whole new level of fun to your adventure by booking your group into one of the 12 houses with a private pool in Roxbury. Use our search filter to find properties with pools on Bookabach, then spend your days frolicking in a swimming pool that’s just for you.
What are popular home amenities in Roxbury?
When it comes to home amenities that guests prefer in Roxbury, a water view, ski-in/ski-out facilities and a sauna are at the top of the list. With Bookabach holiday homes, there are options to match your style and taste, whether you’re going away with your partner, your family or even pets.
Are there large group holiday homes in Roxbury?
With nine properties that can host 10 or more guests in Roxbury, there’s no need to limit the invite list. From extended family holidays to special events like birthday and Christmas parties, Bookabach can help you find a large group home to suit the occasion.
Are there holiday homes in Roxbury that welcome kids?
With 17 family-friendly holiday homes to choose from in Roxbury, now is a fantastic time to introduce your children to the magic of travel. Check our “Properties good for families” filter box to view stays packed with conveniences ideal for holidaying families, like living rooms, outdoor spaces, entertainment units and bunk beds.
What are the top attractions for families in Roxbury?
There are lots of cool things to do and see with the family in Roxbury, such as:

  • Lovers Leap State Park
  • Elephants Trunk Flea Market
  • Pilgrim Mall Shopping Centre

Are there one-bedroom holiday homes in Roxbury?
You can choose from two one-bedroom homes in Roxbury. Whether you’re looking for an apartment or a cabin, Bookabach’s one-bedroom properties are ideal if you don’t need tons of space. One of the major perks of having your own place? You won’t need to share your holiday with strangers.
Are there holiday homes with WiFi in Roxbury?
There are 12 holiday homes with WiFi in Roxbury. If you want to disconnect from the world on your break, but still need to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Roxbury?
Select your dates and then use the filter tool to view holiday homes with ac in Roxbury on Bookabach. With 16 air-conditioned properties available, you can look forward to a comfortable and cool stay.
How old do you have to be to rent a holiday home in Roxbury?
Age restrictions can vary across properties on Bookabach, so check the rules of the holiday home in Roxbury you want to book. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home in Roxbury for?
It’s really down to the Roxbury property. To see all available options offering extended stays, simply type your dates and number of guests into Bookabach. You can enjoy having the whole place to yourself, along with home comforts like a kitchen, air conditioning and a backyard where the kids can run and play. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.

More Holiday Rentals ideas

San Diego Holiday Rentals
Standard Link for San Diego
Breckenridge Holiday Rentals
Standard Link for Breckenridge
Laguna Beach Holiday Rentals
Standard Link for Laguna Beach
Santa Barbara Holiday Rentals
Standard Link for Santa Barbara
Anaheim Holiday Rentals
Standard Link for Anaheim
Honolulu Holiday Rentals
Standard Link for Honolulu
Beach Haven Holiday Rentals
Standard Link for Beach Haven
Riverside Holiday Rentals
Standard Link for Riverside
Oxford Holiday Rentals
Standard Link for Oxford, CT (OXC-Waterbury - Oxford)
Kailua-Kona Holiday Rentals
Standard Link for Kailua-Kona
Haleiwa Holiday Rentals
Standard Link for Haleiwa
Ocean View Holiday Rentals
Standard Link for Ocean View
Kihei Holiday Rentals
Standard Link for Kihei
The Villages Holiday Rentals
Standard Link for The Villages
Hilo Holiday Rentals
Standard Link for Hilo
Snowmass Village Holiday Rentals
Standard Link for Snowmass Village
Laie Holiday Rentals
Standard Link for Laie
Half Moon Bay Holiday Rentals
Standard Link for Half Moon Bay
Charleston Holiday Rentals
Standard Link for Charleston
Park City Holiday Rentals
Standard Link for Park City
Big Sky Holiday Rentals
Standard Link for Big Sky
Aspen Holiday Rentals
Standard Link for Aspen
Kailua Holiday Rentals
Standard Link for Kailua
Yosemite National Park Holiday Rentals
Standard Link for Yosemite National Park
New Life Christian church Holiday Rentals
Standard Link for New Life Christian church
Mystic Holiday Rentals
Standard Link for Mystic
New Haven Holiday Rentals
Standard Link for New Haven
Palm Springs Holiday Rentals
Standard Link for Palm Springs

People also search for

Honolulu apartments
Standard Link for Honolulu
Yosemite National Park cabins
Standard Link for Yosemite National Park