A waterfall cascading over rocks into a clear river surrounded by lush greenery and trees.

Roxbury Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Roxbury holiday rentals

A modern kitchen with a dining area, large windows, and a TV displaying a streaming service.

1. The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is HK$1,144
HK$1,812 total
includes taxes & fees
18 Oct - 19 Oct
The Perch in the Purchase -- Cozy, unique, and private
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

2. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
10.0 out of 10, Exceptional, (1 review)
"Clean and close to activitys"
United States
randall
The price is HK$643
HK$1,257 total
includes taxes & fees
4 Oct - 5 Oct
Cozy private room in a shared home with a Full-size bed and private bathroom.
A white house with a wooden staircase leading to a porch.

3. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is HK$671
HK$928 total
includes taxes & fees
19 Oct - 20 Oct
Cozy One Bedroom Apartment Centrally Located in Southbury
A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

4. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
New Milford
The price is HK$3,707
HK$6,307 total
includes taxes & fees
6 Oct - 7 Oct
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

5. 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
8.4 out of 10, Very good, (12 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is HK$777
HK$1,050 total
includes taxes & fees
5 Oct - 6 Oct
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A multi-story house with a dock and boats, surrounded by dense forest.

6. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, Exceptional, (9 reviews)
"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"
United States
Ron P.
The price is HK$2,730
HK$9,542 total
includes taxes & fees
14 Oct - 15 Oct
North Cliff House - Private Dock & Sauna
A picnic setup with a checkered blanket, a basket, and two wine glasses on a grassy area with a lake and trees in the background.

7. Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
New Fairfield
8.6 out of 10, Excellent, (36 reviews)
"Very serene location, the host was very responsive and helpful."
United States
Stephen L.
The price is HK$918
HK$2,676 total
includes taxes & fees
18 Oct - 19 Oct
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

8. The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (4 reviews)
"Great location and lots to do despite it raining for half our stay! My dog enjoyed the yard and walks around the neighborhood. My son loved kayaking and having his first ever s’more. Honestly I wished we had booked a longer trip! "
United States
Lyndsey F.
The price is HK$2,349
HK$4,330 total
includes taxes & fees
26 Oct - 27 Oct
The Little Lake Cabin with hot tub
A modern kitchen with white cabinets, stainless steel appliances, and a dining table with chairs.

9. Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
10.0 out of 10, Exceptional, (1 review)
"Pro Unit very clean, check in was easy and host was responsive to issues 24/7.Unit is large with new appliances in full kitchen.It is located in a beautiful rural area of CT. I highly recommend it"
United States
Daniel R.
The price is HK$1,091
HK$2,249 total
includes taxes & fees
6 Oct - 7 Oct
Private Apartment in Southbury 104
A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

10. Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.0 out of 10, Wonderful, (6 reviews)
"Over all a great place. Nice to have everything on one floor. Dogs loved it. Some businesses in the building and everyone is friendly!"
United States
Debbie P.
The price is HK$1,020
HK$2,160 total
includes taxes & fees
2 Nov - 3 Nov
Private Apartment in Southbury 102
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

11. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (18 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is HK$1,687
HK$2,160 total
includes taxes & fees
4 Oct - 5 Oct
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A view through a window with a clear sky and lush greenery outside.

12. Private Apartment in Southbury 101

Private Apartment in Southbury 101
Southbury
9.6 out of 10, Exceptional, (7 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
The price is HK$1,130
HK$2,302 total
includes taxes & fees
2 Nov - 3 Nov
Private Apartment in Southbury 101
A two-story house with a porch, a front door with a wreath, and a small garden area.

13. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (9 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is HK$918
HK$2,578 total
includes taxes & fees
8 Oct - 9 Oct
Bear Retreat - 2-bedroom house in Waterbury
A spacious living room with large windows, a fireplace, and a view of the outdoors.

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

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown
9.0 out of 10, Wonderful, (6 reviews)
"In town to visit our new grandchild. It was just my husband and me. It had more then enough room and was very comfortable."
United States
Elizabeth H.
The price is HK$1,718
HK$4,205 total
includes taxes & fees
7 Oct - 8 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A spacious living room with large windows, a fireplace, and a view of the outdoors.

15. 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
The price is HK$2,142
HK$4,229 total
includes taxes & fees
7 Oct - 8 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A modern hotel room with a large bed, a desk with a chair, a flat-screen TV, and a window with curtains.

16. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Bethel
The price is HK$860
HK$989 total
includes taxes & fees
1 Nov - 2 Nov
1 Queen Bed | Non-Smoking
A modern kitchen with white cabinets, a dining area with a black table and chairs, and a large window with curtains.

17. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
The price is HK$1,114
HK$2,307 total
includes taxes & fees
3 Oct - 4 Oct
Private Apartment in Southbury 105
A living room with a fireplace, two armchairs, a sofa, and a TV.

18. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (24 reviews)
"Very nice, great location in town"
United States
Lisa F.
The price is HK$1,300
HK$1,668 total
includes taxes & fees
5 Oct - 6 Oct
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

19. Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
8.0 out of 10, Very good, (1 review)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
United States
Dirk N.
The price is HK$863
HK$1,149 total
includes taxes & fees
4 Oct - 5 Oct
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A compact kitchen with wooden cabinets, a microwave, a sink, and a chair.

20. Cozy Studio apartment in delightful Waterbury with Central Air

Cozy Studio apartment in delightful Waterbury with Central Air
Waterbury
2.0 out of 10, (1 review)
"The place wasn’t how the pictures were on the app. It was hard to find the room. The keys for the room are very hard to open the room door . It’s like you have to struggle just to get inside . The room is inside of an abandoned building… some staff in the building was telling me that I shouldn’t be staying there or they wouldn’t stay there so it made me feel unsafe… the bed doesn’t match the head board. Everything just doesn’t match the images the host posted.."
United States
zynaisha
The price is HK$530
HK$766 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Studio apartment in delightful Waterbury with Central Air
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

The Abner Hotel

The Abner Hotel

10/10 Excellent
"We loved our stay- the room was so well presented/had everything we could need, and we felt so well looked after by all staff. We enjoyed the breakfast, and drinks on the rooftop bar were definitely a highlight! We had dinner one out of the two nights we were staying, which was also lovely. Highly recommend if you’re in the Litchfield area!"
Jessica 2-night trip
Posted 18 hours ago
The Abner Hotel

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?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Roxbury offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Roxbury?

Choose from 12 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 Lovers Leap State Park.

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.