Photo by Jennifer Brokaw

Holiday Rentals in Roxbury

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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, (66)
"My friends and I had a wonderful weekend stay. "
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
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
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!
Beautiful Escape! Hudson Valley LakeHouse. 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 €727
includes taxes & fees
22 Oct - 23 Oct
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
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!
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (21)
"Great stay for 50th birthday "
The price is €808
includes taxes & fees
9 Oct - 10 Oct
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 €229
includes taxes & fees
7 Oct - 8 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
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
10.0 out of 10, Exceptional, (13)
"We had a perfect two night stay at this great house! Exactly as advertised and great views and access to the lake. Our boys loved fishing and kayaking and it’s a nice quiet neighborhood for relaxation. We would definitely go back "
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Tranquil Litchfield Connecticut Retreat".
9.6 out of 10, Exceptional, (5)
"Great property close to all kinds of places to visit and scenic nature!"
The price is €269
includes taxes & fees
8 Oct - 9 Oct
Tranquil Litchfield Connecticut Retreat".
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!
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.
Charming 3BR Hilltop House, Newly Remodeled with Arcade
10.0 out of 10, Exceptional, (18)
"So glad we found this property to accommodate our family of six for the weekend. It was cozy, updated and immaculately clean. The owners seem to have thought of everything and clearly care about providing an exceptional experience. Highly recommend!"
Charming 3BR Hilltop House, Newly Remodeled with Arcade
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...
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
10.0 out of 10, Exceptional, (104)
"Great house! The house is fully stocked with everything which was nice. It had a lot of great areas to sit and relax inside and out. There are a decent amount of steps to the water which was fine for us. The host was very accommodating and responsive. I would recommend this house.we had a great time!"
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
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
Peaceful apartment on 3.5 acres w/ artist studio.
9.2 out of 10, Wonderful, (15)
"We were only here for one night on a whirlwind trip but would gladly have stayed a little longer. Cozy, woodsy and comfy. Nice place to relax and recharge! We really appreciated the excellent (real) coffee! No pods here :) Saleem was great - very helpful!"
The price is €196
includes taxes & fees
6 Oct - 7 Oct
Peaceful apartment on 3.5 acres w/ artist studio.
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!
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Other types of properties in Roxbury you may be interested in

Courtyard by Marriott Waterbury Downtown
3.0 star property
8.4 out of 10, Very good, (1002)
"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 €108
includes taxes & fees
28 Oct - 29 Oct
Courtyard by Marriott Waterbury Downtown
Wyndham Southbury
3.0 star property
8.0 out of 10, Very good, (1002)
"Big. Convenient. Clean. "
The price is €97
includes taxes & fees
3 Nov - 4 Nov
Wyndham Southbury
Microtel Inn & Suites by Wyndham Bethel/Danbury
2.0 star property
8.2 out of 10, Very good, (1001)
"Awesome and micro !! "
The price is €98
includes taxes & fees
3 Nov - 4 Nov
Microtel Inn & Suites by Wyndham Bethel/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 18 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.