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

Roxbury Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Roxbury vacation 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 CA $88
CA $182 total
includes taxes & fees
Nov 9 - Nov 10
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, (39 reviews)
"Charles was super responsive and the bed was amazingly comfortable. Also the shower head great water pressure :-)"
United States
Lisbeth
The price is CA $145
CA $183 total
includes taxes & fees
Dec 1 - Dec 2
Cozy One Bedroom Apartment Centrally Located in Southbury
A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

3. 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 CA $162
CA $347 total
includes taxes & fees
Nov 30 - Dec 1
Private Apartment in Southbury 102
A modern kitchen with white cabinets, stainless steel appliances, and a dining table with chairs.

4. 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 CA $177
CA $366 total
includes taxes & fees
Dec 6 - Dec 7
Private Apartment in Southbury 104
A view through a window with a clear sky and lush greenery outside.

5. 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 CA $183
CA $372 total
includes taxes & fees
Dec 6 - Dec 7
Private Apartment in Southbury 101
A modern hotel room with a bed, bedside table, lamp, desk, and window.

6. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Bethel
10.0 out of 10, Exceptional, (4 reviews)
"Quick check-in and a quiet room made sleeping easy here. Everything felt straightforward without hassle."
United States
Anonymous traveller
The price is CA $153
CA $176 total
includes taxes & fees
Nov 8 - Nov 9
1 Queen Bed | Non-Smoking
A two-story house with a porch, a front door with a wreath, and a small garden area.

7. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (13 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is CA $157
CA $436 total
includes taxes & fees
Nov 7 - Nov 8
Bear Retreat - 2-bedroom house in Waterbury
A modern hotel room with a bed, bedside table, lamp, desk, and window.

8. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Bethel
10.0 out of 10, Exceptional, (3 reviews)
"We found plenty of space for our small group plus pets. Loved having a private bathroom,it made mornings smooth."
United States
Anonymous traveller
The price is CA $160
CA $184 total
includes taxes & fees
Nov 8 - Nov 9
1 King Bed | Non-Smoking
A modern kitchen with white cabinets, a dining area with a black table and chairs, and a large window with curtains.

9. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
The price is CA $177
CA $366 total
includes taxes & fees
Dec 1 - Dec 2
Private Apartment in Southbury 105
A hotel room with two beds, a desk, a chair, and a large window with curtains.

10. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Bethel
10.0 out of 10, Exceptional, (2 reviews)
"Got a good rest before the drive. Place was clean with a refreshing shower and calm enough for sleep."
United States
Anonymous traveller
The price is CA $167
CA $192 total
includes taxes & fees
Nov 8 - Nov 9
2 Queen Beds | Non-Smoking
A modern kitchen with white cabinets, a microwave, stove, and sink. There is a dining area with a table and chairs.

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 CA $154
CA $194 total
includes taxes & fees
Nov 6 - Nov 7
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A living room with a fireplace, two armchairs, a sofa, and a TV.

12. 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 CA $208
CA $257 total
includes taxes & fees
Nov 6 - Nov 7
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

13. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
7.4 out of 10, Good, (3 reviews)
"We had a wonderful experience! The RV was very nice and cozy. Everything was clean and well maintained. The property was beautiful. The host was very helpful and accommodating. Definitely plan on coming back!"
United States
Fernanda
The price is CA $140
CA $245 total
includes taxes & fees
Nov 6 - Nov 7
Welcome to Sweet Abby Rose!
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

14. 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, (21 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is CA $300
CA $372 total
includes taxes & fees
Nov 12 - Nov 13
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A living room with a white sectional sofa, a dining area with a wooden table and chairs, and a staircase leading to an upper level.

15. 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 CA $699
CA $1,155 total
includes taxes & fees
Dec 1 - Dec 2
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

16. 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 CA $342
CA $682 total
includes taxes & fees
Nov 18 - Nov 19
Escape to Bantam Lake- With Fireplace and Hot tub!
A spacious living room with large windows, a fireplace, and a view of the outdoors.

17. 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 CA $306
CA $725 total
includes taxes & fees
Nov 7 - Nov 8
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

18. 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 CA $418
CA $736 total
includes taxes & fees
Nov 10 - Nov 11
The Little Lake Cabin with hot tub
A two-story house with a front porch, a small balcony, and a white picket fence.

19. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.6 out of 10, Exceptional, (7 reviews)
"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 CA $147
CA $478 total
includes taxes & fees
Nov 15 - Nov 16
Cozy Attic 10 min to Llitchfield
A rustic cabin surrounded by a forest with a stream in the foreground.

20. Creek Side Cabin with Wood Fired Hot Tub and Fire Pit

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"Great little house, our favorite part was the gorgeous creek. Absolutely would recommend to pet lovers and those looking for peaceful nature :)"
United States
Kristine W.
The price is CA $363
CA $665 total
includes taxes & fees
Nov 11 - Nov 12
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
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

Hyatt House Shelton

Hyatt House Shelton

8/10 Good
"The rooms were clean and welcoming. Staff welcoming and helpful. Breakfast was great. They were working in the parking lot so not the best. but will not hold that against them as they are flashing it up."
Kevin 2-night trip
Posted less than an hour ago
Hyatt House Shelton

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Roxbury vacation rentals we have selected for you start as low as CA $245 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 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. 

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?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: Visitors like this Roxbury vacation home rental. It offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Roxbury?

Choose from 12 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 Lovers Leap State Park.

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.