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Holiday Rentals in Roxbury

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Holiday Rentals in Roxbury

Litchfield County Four Season Country Paradise

9.6 out of 10, Exceptional, (40)
"Overall rating 5/5. I would recommend this home to other families and would stay again. "
Litchfield County Four Season Country Paradise

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

10.0 out of 10, Exceptional, (15)
"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (13)
"Quick trip"
The price is €284
includes taxes & fees
20 Jul - 21 Jul
Tranquil Litchfield Connecticut Retreat".

Lake Carmel Access: Waterfront Home w/ Deck!

Lake Carmel Access: Waterfront Home w/ Deck!

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

10.0 out of 10, Exceptional, (15)
"Wonderful, comfortable home! Clean, user-friendly with great views!"
The price is €772
includes taxes & fees
25 Jun - 26 Jun
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Quiet 2bd Townhome apt in the heart of Cheshire. Grill in backyard.

10.0 out of 10, Exceptional, (5)
"Overall a positive experience. Property was clean and worked out really well for us as location was close to family we were visiting. We are from Florida, and it was cold in CT and the heat worked great so that was really good. Andrew was responsive to requests. Only criticism was in some of the set up. There are no dressers, so you need to stack your clothes on shelves in closet, which was not terrible. Also, the only mirror in the entire place was in the bathroom downstairs (bedrooms...
The price is €166
includes taxes & fees
29 Jun - 30 Jun
Quiet 2bd Townhome apt in the heart of Cheshire. Grill in backyard.

Connecticut Retreat: Steps to Historic Downtown!

9.6 out of 10, Exceptional, (14)
"Everything was as described and updated we enjoyed our stay. "
Connecticut Retreat: Steps to Historic Downtown!

Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

9.4 out of 10, Exceptional, (91)
"This is a beautiful home even if you live in the area and just want to spend the weekend at the lake, it’s a perfect getaway. We love that it was dog friendly. The host was wonderful and very accommodating. The house came stocked with everything that you would need for a perfect stay. "
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

Cozy Cabin @ Sticks & Stones Farm

8.4 out of 10, Very good, (6)
"Nice clean cabin. Good communication with host."
Cozy Cabin @ Sticks & Stones Farm

Mid-Century Seclusion: An Architectural Marvel w/ Hot Tub

10.0 out of 10, Exceptional, (1)
"peaceful"
Mid-Century Seclusion: An Architectural Marvel w/ Hot Tub

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (41)
"Had an amazing stay. House was stocked with all of the essentials. Fantastic location. Would definitely stay again!"
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

10.0 out of 10, Exceptional, (188)
"The cabin is nestled in a wooded area and the bay window views of the lake while relaxing in front of the fireplace ablaze was perfect! "
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Charming ,affordable, Private 1-bed & 1 ba , safe park. Quiet neighborhood,

9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
The price is €169
includes taxes & fees
21 Jul - 22 Jul
Charming ,affordable, Private 1-bed & 1 ba , safe park. Quiet neighborhood,

Spacious Woodbury Home w/ Pool + Hot Tub!

8.0 out of 10, Very good, (1)
"We rented this place for the first time for a family gathering. The setting was very private and “country-ish”. For the most part everything listed was present at the place and there were enough sleeping options for our crew. Overall - the owners were nice and fairly responsive but there was a level of disappointment to the care of the property and more importantly the preparedness for our arrival. They said the pool and hot tub were cleaned and ready but the pool was still dirty and the hot tub...
Spacious Woodbury Home w/ Pool + Hot Tub!

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (23)
"Clean, Cozy and Comfortable "
Charming 3BR Hilltop House, Newly Remodeled with Arcade

New One Bedroom Apartment Centrally Located in Southbury

9.6 out of 10, Exceptional, (5)
"Excellent place in an excellent location. Charles is a wonderful host. Will be staying there again. "
The price is €116
includes taxes & fees
24 Jun - 25 Jun
New One Bedroom Apartment Centrally Located in Southbury

My favorite place!

2.0 star property
My favorite place!

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

10.0 out of 10, Exceptional, (121)
"My family and I stayed at the Lake House for the holiday. We can not say enough about the amenities, the house & the owners. We look forward to returning to this magical place for our next family reunion."
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

9.6 out of 10, Exceptional, (24)
"Overall it was a great location for a relaxing girls trip. The hot tub and sunroom were great places to hang out. The pictures were very accurate of the house. We did have some issues with cleanliness and pests that we were not expecting. We would recommend it for a relaxing lakefront thing stay."
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

Lake house cozy to relax with a family. 6 bedroom very spacious house.

10.0 out of 10, Exceptional, (1)
"Perfect setting for our family as we celebrated a college graduation locally. Great location. Home has many amenities and you cannot beat lake living! Trying to think about a reason we can return. ;-)"
Lake house cozy to relax with a family. 6 bedroom very spacious house.
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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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?

Litchfield County Four Season Country Paradise: This highly rated holiday home rental in Roxbury is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Roxbury?

Choose from 15 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 Quassy Amusement Park, 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.