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Roxbury Holiday Rentals

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Holiday Rentals in Roxbury

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Cheshire
9.2 out of 10, Wonderful, (11)
"Very nice location in a country setting. Saw deer in the backyard every morning. Very clean and accurate description of the property. Friendly hosts who supplied everything we needed. Would stay here again. Highly recommend."
United States
Eileen A.
The price is NZ$287
includes taxes & fees
17 Nov - 18 Nov
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

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 NZ$215
includes taxes & fees
17 Nov - 18 Nov
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Torrington
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 NZ$481
includes taxes & fees
17 Nov - 18 Nov
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Shelton
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 NZ$346
includes taxes & fees
17 Nov - 18 Nov
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Private Apartment in Southbury 101

Southbury
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 NZ$518
includes taxes & fees
1 Dec - 2 Dec
Private Apartment in Southbury 101

#31 - Downtown Terryville- 1 Br

Plymouth
10.0 out of 10, Exceptional, (1)
"In convenient safe area. Os is easy to contact"
United States
Gina P.
The price is NZ$415
includes taxes & fees
22 Nov - 23 Nov
#31 - Downtown Terryville- 1 Br

Cozy Modern Farmhouse Private 2 Bdrm Apartment

Torrington
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 NZ$555
includes taxes & fees
1 Dec - 2 Dec
Cozy Modern Farmhouse Private 2 Bdrm Apartment

New One Bedroom Apartment Centrally Located in Southbury

Southbury
9.8 out of 10, Exceptional, (16)
"Excellent stay !!!! Everything was perfect. Communication was phenomenal.!!!!"
United States
daniellle
The price is NZ$226
includes taxes & fees
23 Nov - 24 Nov
New One Bedroom Apartment Centrally Located in Southbury

Private Apartment in Southbury 102

Southbury
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 NZ$506
includes taxes & fees
17 Nov - 18 Nov
Private Apartment in Southbury 102

Private Apartment in Southbury 103

Southbury
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 NZ$518
includes taxes & fees
1 Dec - 2 Dec
Private Apartment in Southbury 103

Peaceful apartment on 3.5 acres w/ artist studio.

Brookfield
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 NZ$341
includes taxes & fees
17 Nov - 18 Nov
Peaceful apartment on 3.5 acres w/ artist studio.

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

3.0 star property
Oakville
The price is NZ$750
includes taxes & fees
17 Nov - 18 Nov
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Charming apartment 7 minute walk to downtown

Torrington
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 NZ$435
includes taxes & fees
19 Nov - 20 Nov
Charming apartment 7 minute walk to downtown

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Carmel Hamlet
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 NZ$625
includes taxes & fees
17 Nov - 18 Nov
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

The Hideaway

Brewster
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 NZ$557
includes taxes & fees
17 Nov - 18 Nov
The Hideaway

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

2.0 star property
Shelton
The price is NZ$691
includes taxes & fees
17 Nov - 18 Nov
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Cozy cute Relaxing home

Southbury
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 NZ$552
includes taxes & fees
17 Nov - 18 Nov
Cozy cute Relaxing home

1-bedroom vacation home 22 minutes from Quinnipiac University

Wolcott
9.6 out of 10, Exceptional, (4)
"Very clean and the host was great "
United States
David G.
The price is NZ$698
includes taxes & fees
30 Nov - 1 Dec
1-bedroom vacation home 22 minutes from Quinnipiac University

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

New Fairfield
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 NZ$854
includes taxes & fees
1 Dec - 2 Dec
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

#9 - STUNNING*RENOVATED* *4BR HOUSE*

Southington
10.0 out of 10, Exceptional, (1)
"Great property"
United States
MICHAEL S.
The price is NZ$961
includes taxes & fees
29 Nov - 30 Nov
#9 - STUNNING*RENOVATED* *4BR HOUSE*
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

Find out more about Roxbury

Everything you need to know about Roxbury holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Roxbury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Roxbury holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Roxbury holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Roxbury. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Roxbury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Roxbury holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Roxbury rentals

At Expedia, we put the best Roxbury holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Roxbury rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Roxbury holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Roxbury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.