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Roxbury Vacation Rentals

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Nov 17 - Nov 18
Tomorrow
Nov 18 - Nov 19
This weekend
Nov 21 - Nov 23
Next weekend
Nov 28 - Nov 30

Vacation Rentals in Roxbury

Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

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.
$145 nightly
The price is $163
Nov 18 - Nov 19
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
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.

Watertown
9.8 out of 10, Exceptional, (7)
"Great place, friendly people as usual! Love the place! We always enjoy our stay! Thanks again Brian and Laurie "
United States
Laurie P.
$109 nightly
The price is $122
Nov 18 - Nov 19
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Torrington
9.6 out of 10, Exceptional, (4)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
$230 nightly
The price is $274
Nov 18 - Nov 19
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
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,

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.
$174 nightly
The price is $197
Nov 18 - Nov 19
Total with taxes and fees
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Interior
Private Apartment in Southbury 101

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.
$260 nightly
The price is $295
Dec 16 - Dec 17
Total with taxes and fees
Private Apartment in Southbury 101
Interior
#31 - Downtown Terryville- 1 Br

#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.
$221 nightly
The price is $236
Nov 22 - Nov 23
Total with taxes and fees
#31 - Downtown Terryville- 1 Br
Exterior
Cozy Modern Farmhouse Private 2 Bdrm Apartment

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.
$261 nightly
The price is $312
Dec 1 - Dec 2
Total with taxes and fees
Cozy Modern Farmhouse Private 2 Bdrm Apartment
Exterior
New One Bedroom Apartment Centrally Located in Southbury

New One Bedroom Apartment Centrally Located in Southbury

Southbury
9.8 out of 10, Exceptional, (16)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
$115 nightly
The price is $129
Nov 23 - Nov 24
Total with taxes and fees
New One Bedroom Apartment Centrally Located in Southbury
Property grounds
Private Apartment in Southbury 102

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.
$246 nightly
The price is $279
Nov 18 - Nov 19
Total with taxes and fees
Private Apartment in Southbury 102
Fridge, microwave, oven, stovetop
Private Apartment in Southbury 103

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.
$253 nightly
The price is $287
Dec 16 - Dec 17
Total with taxes and fees
Private Apartment in Southbury 103
Game room
Peaceful apartment on 3.5 acres w/ artist studio.

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.
$172 nightly
The price is $195
Nov 18 - Nov 19
Total with taxes and fees
Peaceful apartment on 3.5 acres w/ artist studio.
House (3 Bedrooms) | 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
Oakville
$371 nightly
The price is $426
Nov 18 - Nov 19
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Fridge, microwave, oven, stovetop
Charming apartment 7 minute walk to downtown

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.
$218 nightly
The price is $247
Nov 19 - Nov 20
Total with taxes and fees
Charming apartment 7 minute walk to downtown
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.

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.
$328 nightly
The price is $355
Nov 19 - Nov 20
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Property grounds
The Hideaway

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.
$292 nightly
The price is $316
Nov 18 - Nov 19
Total with taxes and fees
The Hideaway
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
Shelton
$343 nightly
The price is $389
Nov 18 - Nov 19
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Terrace/patio
Cozy cute Relaxing home

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.
$277 nightly
The price is $314
Nov 18 - Nov 19
Total with taxes and fees
Cozy cute Relaxing home
Exterior detail
1-bedroom vacation home 22 minutes from Quinnipiac University

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.
$350 nightly
The price is $397
Nov 30 - Dec 1
Total with taxes and fees
1-bedroom vacation home 22 minutes from Quinnipiac University
Outdoor dining
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

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.
$398 nightly
The price is $450
Dec 1 - Dec 2
Total with taxes and fees
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
Fridge, microwave, oven, stovetop
#9 - STUNNING*RENOVATED* *4BR HOUSE*

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

Southington
10.0 out of 10, Exceptional, (1)
"Great property"
United States
MICHAEL S.
#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

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

10/10 Excellent
"Staff was great. Everything was wonderful!!"
Nuri 2-night trip
Posted 2 days ago
Courtyard by Marriott Waterbury Downtown

Find out more about Roxbury

Everything you need to know about Roxbury vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Roxbury vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Roxbury vacation 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 low season months. For more hustle and bustle, you may prefer to visit Roxbury in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $129 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Roxbury rentals

At Expedia, we put the best Roxbury vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Roxbury?

Yes, you can find vacation rentals near well known sights in Roxbury, or you can select a more remote option if you're looking for relaxation.

What's the top vacation rental that Roxbury has to offer?

Litchfield County Four Season Country Paradise: Visitors like this Roxbury vacation home rental. It is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Roxbury?

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

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 larger area, you’ll find Steep Rock Preserve and Elephant's Trunk Flea Market.

What’s a vacation rental in Roxbury like?

A vacation rental is a private property you can book for a long or short time in Roxbury. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a family getaway.