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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Roxbury holiday rentals

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

1. 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, (3 reviews)
"I really enjoyed my four night stay here."
United States
Jim B.
The price is AU$207
includes taxes & fees
3 Nov - 4 Nov
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.

2. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (38 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is AU$201
includes taxes & fees
2 Nov - 3 Nov
Cozy One Bedroom Apartment Centrally Located in Southbury
A modern kitchen with a dining area, large windows, and a TV displaying a streaming service.

3. 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, (6 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is AU$344
includes taxes & fees
28 Oct - 29 Oct
The Perch in the Purchase -- Cozy, unique, and private
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

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 AU$205
includes taxes & fees
4 Nov - 5 Nov
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

5. Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.2 out of 10, Wonderful, (7 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 AU$354
includes taxes & fees
25 Oct - 26 Oct
Private Apartment in Southbury 102
A view through a window with a clear sky and lush greenery outside.

6. 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 AU$376
includes taxes & fees
25 Oct - 26 Oct
Private Apartment in Southbury 101
A modern kitchen with white cabinets, stainless steel appliances, and a dining table with chairs.

7. 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.
Private Apartment in Southbury 104
A two-story house with a porch, a front door with a wreath, and a small garden area.

8. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (11 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is AU$469
includes taxes & fees
1 Nov - 2 Nov
Bear Retreat - 2-bedroom house in Waterbury
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

9. 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, (20 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is AU$391
includes taxes & fees
26 Oct - 27 Oct
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A vending machine with various snacks and drinks.

10. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Bethel
The price is AU$187
includes taxes & fees
25 Oct - 26 Oct
1 King Bed | Non-Smoking
A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

11. 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 AU$211
includes taxes & fees
25 Oct - 26 Oct
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

12. Escape to Bantam Lake- With Fireplace and Hot tub!

Escape to Bantam Lake- With Fireplace and Hot tub!
Morris
10.0 out of 10, Exceptional, (6 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
United States
Shannon M.
The price is AU$670
includes taxes & fees
15 Nov - 16 Nov
Escape to Bantam Lake- With Fireplace and Hot tub!
A bedroom with a bed, a dresser, and a window with curtains.

13. 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
10.0 out of 10, Exceptional, (1 review)
"Perfect!!"
United States
Jeni O.
The price is AU$1,237
includes taxes & fees
27 Oct - 28 Oct
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A multi-story house with a dock and boats, surrounded by dense forest.

14. 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 AU$1,784
includes taxes & fees
26 Oct - 27 Oct
North Cliff House - Private Dock & Sauna
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!
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 AU$753
includes taxes & fees
27 Oct - 28 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A modern kitchen with white cabinets, a dining area with a black table and chairs, and a large window with curtains.

16. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
The price is AU$420
includes taxes & fees
17 Nov - 18 Nov
Private Apartment in Southbury 105
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

17. The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (6 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 AU$833
includes taxes & fees
5 Nov - 6 Nov
The Little Lake Cabin with hot tub
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
9.8 out of 10, Exceptional, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
The price is AU$323
includes taxes & fees
3 Nov - 4 Nov
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A hotel room with a bed, a desk with a chair, a television, and a window with curtains.

19. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Bethel
The price is AU$195
includes taxes & fees
25 Oct - 26 Oct
2 Queen Beds | Non-Smoking
A modern hotel room with a large bed, bedside tables, a desk, and a chair.

20. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Bethel
The price is AU$179
includes taxes & fees
25 Oct - 26 Oct
1 Queen Bed | Non-Smoking
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

8/10 Good
"Room was clean but very "sparse" in decor. I felt ww were given less than standard room because of booking it through Expedia. Floors had no carpeting as if was one of the room rented to travelers with pets. Ice machine near room was broken and working one was on other side of property. Also surprise that side door by parking lot did require a key card and was unlocked 24/7. Facility didn't seem to be operating at optimum level."
Christine 1-night trip
Posted 7 hours ago
Wyndham Southbury

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 favourite 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 depend 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 AU$211 per night. Entering your travel dates in the search wizard might find you 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?

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.