Photo by Jennifer Brokaw

Roxbury Holiday Rentals

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Holiday Rentals in Roxbury

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (64)
"The good: We had a great time staying here. The first and second floor are beautiful and very well maintained. Both bathrooms and three bedrooms are very clean and have more than enough bath and beach towels. The fire pit and kayaks are also a great touch. The water is just steps away and the view is excellent. Just be sure to bring your own propane and firewood. What could be better? Communication with the host left a lot to be desired. I’m still not sure who runs the property. There are two...
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
9.4 out of 10, Exceptional, (82)
"Property was clean, well appointed, wish we could have stayed a bit longer to enjoy more of the lake & fire pit! "
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, (7)
"Absolutely loved our stay! The house was cozy, comfortable, and well-equipped. The host was responsive and made sure everything was just right. Highly recommend!!"
The price is AU$1,342
includes taxes & fees
30 Sept - 1 Oct
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (21)
"Great stay for 50th birthday "
Lakeview Estate - Chef's Kitchen - NYC Getaway
Beautiful cozy rooms near hospital and down town area
8.0 out of 10, Very good, (14)
"Overall good experience. Location was great"
The price is AU$363
includes taxes & fees
30 Sept - 1 Oct
Beautiful cozy rooms near hospital and down town area
The Goshen Glass Chalet
9.4 out of 10, Exceptional, (24)
"Everything was clean, and was a very comfortable home for friends and family."
The Goshen Glass Chalet
Newly renovated cottage on the lake!
10.0 out of 10, Exceptional, (18)
"This cabin was perfect for a place to rest and refresh after hiking some of Litchfield area's trails. It was as described by the host and he was very easy to reach with questions. We recommend this cabin as well-located for all that Litchfield county has to offer. "
Newly renovated cottage on the lake!
Lakefront Home, Close to Mt Southington!
10.0 out of 10, Exceptional, (12)
"Staff very much enjoyed the atmosphere after long days of work. Wonderful Ownership. Thank you so much Susan!"
Lakefront Home, Close to Mt Southington!
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
10.0 out of 10, Exceptional, (12)
"The house is huge and is very well equiped. Owners are very responsive to any questions or issues. Wonderful stay for the family."
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, (13)
"Deer Ridge Cabin was wonderful! Very clean with a cozy relaxing atmosphere. Nice accommodations with everything one would need. Its obvious that host Mariana put alot of time and thought into creating a warm inviting environment. I would surely recommend a stay at Deer Ridge Cabin. Thank you, Dana"
Cozy & Chic Cabin by the Lake, with access to private Beach!
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
9.8 out of 10, Exceptional, (23)
"We stayed for 3 weeks it was lovely!"
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
9.8 out of 10, Exceptional, (16)
"Gorgeous home and property, loved being on the lake with the game room cabana, the outdoor areas are so relaxing, and the home is so tastefully decorated. We enjoyed it so much!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, (10)
"Liked outdoor area and fire place "
Candlewood Lake Retreat with year round views
Candlewood Lake Grand Waterfront Oasis: A Luxurious Family Retreat
10.0 out of 10, Exceptional, (39)
"This home is quite lovely and the manager/owners were very responsive throughout booking and during our stay and were very easy to work with. The waterfront area is fantastic, however, it is across the main lake road, and while the speed limit is 25 mph, most cars are going well above that. There are quite a few stairs to get down to the waterfront which is not obvious from the listing photos. This presented a challenge for my 86 year old mother and sister with knee issues. So this is...
Candlewood Lake Grand Waterfront Oasis: A Luxurious Family Retreat
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
10.0 out of 10, Exceptional, (78)
"Very large house just like the photos. Host is present and responsive. We had the entire property to ourselves. Nice yard for some whiffle ball and outdoor activities. Swimming is possible at the public lake access which is about a mile away or so. Overall, a very nice stay at a very nice property. We were 10 adults (friends weekend) and fit just fine. "
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Traveling Nurse or Business Professional
10.0 out of 10, Exceptional, (7)
"The neighborhood was clean, upscale, and beautifully kept. It came with Candlewood Beach access. The second story suite was gorgeous, clean, and well apportioned. The bed was comfortable. The whole house was well maintained and a wonderful,"homey" feel to it. The Hostess was friendly, cheerful, and very accommodating. The house is on the hillside leading to Lake Candlewood. As can be imagined, the views from the windows were outstanding."
Traveling Nurse or Business Professional
Idillic summer getaway in Litchfield Hills, CT.
10.0 out of 10, Exceptional, (12)
"The property was lovely and the property manager was very friendly and accommodating. The space was ample, beds were very comfortable, and the a/c kept us cool in the middle of a heat wave. Only issue was that the house had a very musty smell to it. Also, the coffee pot was filled with old coffee-apparently they forgot to clean it prior to our arrival. Otherwise a great stay!"
Idillic summer getaway in Litchfield Hills, CT.
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, (24)
"This is a really lovely and clean home. The owners were very responsive and clearly take great care with the property and rental process. It was very comfortable for me, my mother and my four year old daughter. The lake view is gorgeous and peaceful, however be advised that CT lakes can sometimes get high bacteria levels so it was not swim friendly when we were there "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT
9.8 out of 10, Exceptional, (10)
"Amenities galore in this well equipped beautiful home! Everyone was happily entertained with the many water play options and many indoor games and activities. The dock and lake were frequently used by all as we also rented a pontoon boat. Wonderful location for our large family to spend time together!"
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT
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Other types of properties in Roxbury you may be interested in

Courtyard by Marriott Waterbury Downtown
3.0 star property
8.2 out of 10, Very good, (1003)
"We live in NY, and were in town for a family funeral. The viewing was about 1 mile away from the Marriott. We were able to check in, freshen up, and make it to the wake and pay our respects to a our military veteran family member. Except for our family loss, the check in, room, parking and travel were all without issue. "
The price is AU$154
includes taxes & fees
13 Oct - 14 Oct
Courtyard by Marriott Waterbury Downtown
Hilton Garden Inn Shelton
3.0 star property
7.6 out of 10, Good, (1003)
"Our room was clean, but overall the property appeared a bit long in the tooth."
The price is AU$190
includes taxes & fees
28 Oct - 29 Oct
Hilton Garden Inn Shelton
Hotel Zero Degrees Danbury
4.0 star property
9.0 out of 10, Wonderful, (1000)
"Only spent a night but the staff was wonderful the moment I walked in. "
The price is AU$290
includes taxes & fees
20 Oct - 21 Oct
Hotel Zero Degrees Danbury
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.

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, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock: This holiday home rental outside of Roxbury is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Roxbury?

Choose from 17 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 Elephant's Trunk Flea Market.

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.