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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Roxbury holiday rentals

Exterior

1. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (36 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
The price is HK$727
HK$994 total
includes taxes & fees
8 Sept - 9 Sept
Cozy One Bedroom Apartment Centrally Located in Southbury
Outdoor dining

2. 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, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is HK$1,144
HK$1,828 total
includes taxes & fees
25 Aug - 26 Aug
The Perch in the Purchase -- Cozy, unique, and private
Coffee/tea maker, fridge, microwave, oven

3. 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$678
HK$1,743 total
includes taxes & fees
17 Aug - 18 Aug
Private Apartment in Southbury 104
Interior

4. 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$855
HK$1,141 total
includes taxes & fees
8 Sept - 9 Sept
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Coffee/tea maker, fridge, microwave, oven

5. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
10.0 out of 10, Exceptional, (4 reviews)
"Property management team was very quick to respond to any question or issue I had. Excellent location around eateries and activities "
United States
Dominick S.
The price is HK$879
HK$1,997 total
includes taxes & fees
19 Aug - 20 Aug
Private Apartment in Southbury 103
1 bedroom, Internet, bed sheets

6. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (1 review)
"The place is super comfortable and has a great outdoor area for chatting; I would definitely like to come back and stay longer."
United States
Yasmin G.
The price is HK$785
HK$1,463 total
includes taxes & fees
24 Aug - 25 Aug
Welcome to Sweet Abby Rose!
Interior

7. 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$1,138
HK$2,334 total
includes taxes & fees
9 Sept - 10 Sept
Private Apartment in Southbury 101
Interior

8. 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$824
HK$1,926 total
includes taxes & fees
19 Aug - 20 Aug
Private Apartment in Southbury 102
Property grounds

9. Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"The accommodations were wonderful and comfortable."
United States
Chuck S.
The price is HK$863
HK$1,624 total
includes taxes & fees
7 Sept - 8 Sept
Hoppy Hill Farm House
Property grounds

10. Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (9 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
The price is HK$629
HK$1,048 total
includes taxes & fees
17 Aug - 18 Aug
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Interior

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, (14 reviews)
"The property was very clean and inviting and the owner was very welcoming and helpful!"
United States
Sarah
The price is HK$1,687
HK$2,183 total
includes taxes & fees
17 Aug - 18 Aug
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Smart TV, fireplace, books

12. 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, (23 reviews)
"Clean, quiet, well stocked studio with everything we needed for our weekend in Kent. Very convenient to town. Highly recommend!"
United States
Joy P.
The price is HK$1,530
HK$1,940 total
includes taxes & fees
23 Aug - 24 Aug
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Interior

13. 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$1,150 total
includes taxes & fees
8 Sept - 9 Sept
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Exterior

14. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.4 out of 10, Exceptional, (6 reviews)
"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.
The price is HK$667
HK$2,133 total
includes taxes & fees
17 Aug - 18 Aug
Cozy Attic 10 min to Llitchfield
Interior

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$4,230 total
includes taxes & fees
14 Sept - 15 Sept
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Interior

16. 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)
"Everything was good just needed to have a tV in each room trash cans also"
United States
Deborah B.
The price is HK$1,718
HK$4,261 total
includes taxes & fees
15 Sept - 16 Sept
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Dining

17. Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is HK$1,103
HK$3,407 total
includes taxes & fees
17 Aug - 18 Aug
Art House 3 Beds Close to Warner Theater
Exterior

18. Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is HK$1,013
HK$2,645 total
includes taxes & fees
17 Aug - 18 Aug
Cozy Modern Farmhouse Private Apt - 3 Beds
Cookware/dishes/utensils

19. Awesome Lake Home with tons of fun!

Awesome Lake Home with tons of fun!
New Fairfield
9.8 out of 10, Exceptional, (11 reviews)
"Nicole is a wonderful host. We had a fantastic stay at her house. The home was beautifully prepared, and we felt very comfortable throughout our visit. Even though it was a rainy weekend, we were still able to enjoy the huge hot tub and had a great time playing the card games and board games provided. Thank you!!"
United States
W Y.
The price is HK$3,531
HK$6,089 total
includes taxes & fees
23 Aug - 24 Aug
Awesome Lake Home with tons of fun!
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

Comfort Inn & Suites Danbury-Bethel

Comfort Inn & Suites Danbury-Bethel

10/10 Excellent
"The room was very clean and all the staff were very friendly!"
Debra 1-night trip
Posted 1 hour ago
Comfort Inn & Suites Danbury-Bethel

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
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  • 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?

Well laid out 2-bedroom private home in Washington-close to the green and depot: 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. Kitchen amenities include a dishwasher, a stovetop and a microwave. Make the most of garden in this rental home to help you unwind.

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.