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Roxbury Holiday Rentals

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Check prices for these dates

In two weeks
21 Nov - 23 Nov
In two months
2 Jan - 4 Jan
In three months
30 Jan - 1 Feb
In four months
27 Feb - 1 Mar

Holiday Rentals in Roxbury

Interior
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
9.8 out of 10, Exceptional, (7)
"The neighborhood is charming, quiet, and safe. The room is filled with amenities and is cleanly. "
United States
Michael A.
The price is HK$692
HK$951 total
includes taxes & fees
18 Nov - 19 Nov
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.4 out of 10, Exceptional, (9)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is HK$658
HK$1,270 total
includes taxes & fees
19 Nov - 20 Nov
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Exterior
New One Bedroom Apartment Centrally Located in Southbury
New One Bedroom Apartment Centrally Located in Southbury
9.8 out of 10, Exceptional, (16)
"Excellent stay !!!! Everything was perfect. Communication was phenomenal.!!!!"
United States
daniellle
The price is HK$754
HK$1,023 total
includes taxes & fees
1 Dec - 2 Dec
New One Bedroom Apartment Centrally Located in Southbury
Interior
Private Apartment in Southbury 101
Private Apartment in Southbury 101
9.4 out of 10, Exceptional, (6)
"Great stay. Clean, open space, easy access, and a nice pond in back to bring the dog. Would come back again."
United States
Rooster D.
The price is HK$917
HK$2,264 total
includes taxes & fees
1 Dec - 2 Dec
Private Apartment in Southbury 101
Interior
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
The price is HK$933
HK$1,530 total
includes taxes & fees
19 Nov - 20 Nov
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Fridge, microwave, oven, stovetop
Private Apartment in Southbury 103
Private Apartment in Southbury 103
10.0 out of 10, Exceptional, (2)
"The host was amazing! We had no problems at all whatsoever. "
United States
Manduella F.
The price is HK$902
HK$2,246 total
includes taxes & fees
12 Nov - 13 Nov
Private Apartment in Southbury 103
Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
9.6 out of 10, Exceptional, (4)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is HK$692
HK$2,119 total
includes taxes & fees
1 Dec - 2 Dec
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Interior
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
The price is HK$1,462
HK$3,313 total
includes taxes & fees
18 Nov - 19 Nov
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Exterior detail
1-bedroom vacation home 22 minutes from Quinnipiac University
1-bedroom vacation home 22 minutes from Quinnipiac University
9.6 out of 10, Exceptional, (4)
"Very clean and the host was great "
United States
David G.
The price is HK$1,166
HK$3,083 total
includes taxes & fees
7 Dec - 8 Dec
1-bedroom vacation home 22 minutes from Quinnipiac University
Fridge, microwave, oven, stovetop
Charming apartment 7 minute walk to downtown
Charming apartment 7 minute walk to downtown
10.0 out of 10, Exceptional, (15)
"We had an amazing stay. The property was very clean and welcoming. Personal touches made us feel at home. A great location close to walking path and downtown. Would highly recommend! "
United States
jennifer b.
The price is HK$1,036
HK$1,922 total
includes taxes & fees
9 Nov - 10 Nov
Charming apartment 7 minute walk to downtown
Games room
Peaceful apartment on 3.5 acres w/ artist studio.
Peaceful apartment on 3.5 acres w/ artist studio.
9.6 out of 10, Exceptional, (19)
"This adorable cottage attached to the main house was fabulous for my wife and I for 4 nights! It has a little kitchen, space heaters everywhere (us southerners can’t handle the New England winters like we used to!) and was very clean! We have never stayed in an attached rental before and I would say we would be open to exploring more because of our experience! "
United States
Mike M.
The price is HK$980
HK$1,506 total
includes taxes & fees
19 Nov - 20 Nov
Peaceful apartment on 3.5 acres w/ artist studio.
Exterior
Cozy Modern Farmhouse Private 2 Bdrm Apartment
Cozy Modern Farmhouse Private 2 Bdrm Apartment
10.0 out of 10, Exceptional, (4)
"We were happy to have a clean and comfortable place to stay while in Torrington visiting family. The hotels in town are nasty so this was a great alternative. There is a park across the street and an Office warehouse on the street behind, so it’s quiet at night which was a plus. Inside is definitely as advertised, cozy but not cramped, the furniture and decor is well appointed. We will definitely stay again."
United States
Kelly Grace G.
The price is HK$941
HK$2,459 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Modern Farmhouse Private 2 Bdrm Apartment
Property grounds
Private Apartment in Southbury 102
Private Apartment in Southbury 102
9.6 out of 10, Exceptional, (4)
"This is a beautiful place to stay. I loved the kitchen, which was well stocked with appliances like a kcup machine and coffee pods and everything was extremely clean. The bed was comfortable and the bathroom was large. Check-in was a little difficult because the door wasn’t labeled the same way the surrounding doors were labeled so I had some trouble finding it but the owner called me that evening to help me find the correct door. The AC was strong and consistent and the couch was comfy. The...
United States
Abigail O.
The price is HK$917
HK$2,264 total
includes taxes & fees
1 Dec - 2 Dec
Private Apartment in Southbury 102
Fridge, microwave, oven, stovetop
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Mid Century Modern Studio w/ Full Kitchen - Newly Built
9.8 out of 10, Exceptional, (6)
"Super cute, clean, and convenient for our quick trip to The Millbrook School."
United States
Carol H.
The price is HK$1,749
HK$2,222 total
includes taxes & fees
7 Dec - 8 Dec
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Property grounds
The Hideaway
The Hideaway
10.0 out of 10, Exceptional, (6)
"Me and my family stayed here for a quick get-away out of the city. Very pretty location, and loved our stay here! Thanks!"
United States
Rick C.
The price is HK$1,205
HK$2,460 total
includes taxes & fees
17 Nov - 18 Nov
The Hideaway
3 bedrooms, iron/ironing board, travel cot, WiFi
"Country outside the city " 3 bedrooms 2 full bathrooms
"Country outside the city " 3 bedrooms 2 full bathrooms
2.0 star property
9.6 out of 10, Exceptional, (4)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is HK$1,910
HK$4,984 total
includes taxes & fees
10 Nov - 11 Nov
"Country outside the city " 3 bedrooms 2 full bathrooms
Terrace/patio
Cozy cute Relaxing home
Cozy cute Relaxing home
8.8 out of 10, Excellent, (6)
"Very nice , in general. Only problem was with downstairs TV, remote wouldn't work"
United States
Nancy K.
The price is HK$1,283
HK$2,455 total
includes taxes & fees
7 Dec - 8 Dec
Cozy cute Relaxing home
Fridge, microwave, oven, stovetop
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
2.0 star property
The price is HK$882
HK$3,173 total
includes taxes & fees
4 Dec - 5 Dec
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
TV, fireplace
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is HK$1,294
HK$2,759 total
includes taxes & fees
17 Nov - 18 Nov
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Outdoor dining
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
10.0 out of 10, Exceptional, (34)
"Cozy 3BR apartment in a perfect location for families with young kids (4 & 1). Kevin and Kim were fantastic hosts, even lending us toys for sledding! The home was wonderful, and our 4-year-old loved the nearby beginner ski lessons—highly recommended!"
United States
Maria Eugenia P.
The price is HK$1,924
HK$3,472 total
includes taxes & fees
10 Nov - 11 Nov
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Roxbury Hotel Reviews

Wyndham Southbury

Wyndham Southbury

10/10 Excellent
"Staff at the desk were very helpful and nice."
Joy 3-night trip
Posted 21 hours ago
Wyndham Southbury

Find out more about Roxbury

Search for holiday rentals in Roxbury on Expedia! You can easily find your home rentals, villas, holiday apartments in Roxbury using one of the methods below:

  • View our selection of featured holiday rentals in Roxbury
  • Use the map to find apartments and other holiday homes in the Roxbury neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Roxbury while they last

Look no further and take a look at our great range of rental properties in Roxbury!

Frequently asked questions

Can I find holiday rentals in Roxbury?

Yes, there are holiday rentals close to the most popular sights in Roxbury, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Roxbury has to offer?

Litchfield County Four Season Country Paradise: This highly rated holiday home rental in Roxbury is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Roxbury?

Choose from 15 Expedia holiday rentals in Roxbury for a memorable holiday.

What’s there to see and do in Roxbury?

Explore the area and family-friendly sights such as The Christmas Shop, or get out into nature at a spot like Lake Lillinonah. In the wider area, you’ll find Steep Rock Preserve and Elephant's Trunk Flea Market.

What’s a holiday rental in Roxbury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Roxbury. Holiday rentals provide amenities such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a family trip.