Roxbury Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Roxbury vacation rentals

Exterior

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Torrington
9.2 out of 10, Wonderful, (5 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
The price is ￥13,079
￥52,079 total
includes taxes & fees
Jan 26 - Jan 27
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Interior

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
8.6 out of 10, Excellent, (10 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is ￥13,857
￥19,050 total
includes taxes & fees
Jan 26 - Jan 27
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Fridge, microwave, oven, stovetop

Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
10.0 out of 10, Exceptional, (2 reviews)
"Property management team was very quick to respond to any question or issue I had. Excellent location around eateries and activities "
United States
Dominick S.
The price is ￥13,367
￥39,272 total
includes taxes & fees
Jan 26 - Jan 27
Private Apartment in Southbury 103
Smart TV

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.2 out of 10, Wonderful, (15 reviews)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is ￥14,013
￥26,391 total
includes taxes & fees
Jan 26 - Jan 27
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (22 reviews)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is ￥14,324
￥19,587 total
includes taxes & fees
Jan 26 - Jan 27
Cozy One Bedroom Apartment Centrally Located in Southbury
Interior

Private Apartment in Southbury 101

Private Apartment in Southbury 101
Southbury
9.4 out of 10, Exceptional, (6 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
The price is ￥16,504
￥43,035 total
includes taxes & fees
Feb 2 - Feb 3
Private Apartment in Southbury 101
Fridge, microwave, oven, stovetop

Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.2 out of 10, Wonderful, (5 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 ￥14,029
￥40,190 total
includes taxes & fees
Jan 26 - Jan 27
Private Apartment in Southbury 102
Interior

Cozy & Serene Cabin with Fireplace, Ski Nearby!

Cozy & Serene Cabin with Fireplace, Ski Nearby!
Bethlehem
10.0 out of 10, Exceptional, (37 reviews)
"Very comfortable property. The host had thought of everything!"
United States
Jennifer Y.
The price is ￥28,026
￥62,202 total
includes taxes & fees
Feb 2 - Feb 3
Cozy & Serene Cabin with Fireplace, Ski Nearby!
House (3 Bedrooms) | Interior

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is ￥22,888
￥66,296 total
includes taxes & fees
Jan 27 - Jan 28
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Outdoor dining

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, (1 review)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is ￥19,674
￥32,161 total
includes taxes & fees
Feb 2 - Feb 3
The Perch in the Purchase -- Cozy, unique, and private
Dining

Cozy 1-bedroom apartment in lovely Oxford

Cozy 1-bedroom apartment in lovely Oxford
Oxford
The price is ￥17,438
￥24,958 total
includes taxes & fees
Jan 26 - Jan 27
Cozy 1-bedroom apartment in lovely Oxford
TV, fireplace

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (12 reviews)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is ￥25,924
￥55,093 total
includes taxes & fees
Jan 26 - Jan 27
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
1 bedroom, iron/ironing board, free WiFi, bed sheets

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Shelton
9.0 out of 10, Wonderful, (2 reviews)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
The price is ￥18,684
￥30,642 total
includes taxes & fees
Jan 26 - Jan 27
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Exterior

Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is ￥18,801
￥60,558 total
includes taxes & fees
Jan 26 - Jan 27
Cozy Modern Farmhouse Private Apt - 3 Beds
2 bedrooms, desk, free WiFi, bed sheets

Charming apartment 7 minute walk to downtown

Charming apartment 7 minute walk to downtown
Torrington
10.0 out of 10, Exceptional, (16 reviews)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
The price is ￥21,954
￥40,039 total
includes taxes & fees
Feb 2 - Feb 3
Charming apartment 7 minute walk to downtown
Dining

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is ￥18,801
￥60,558 total
includes taxes & fees
Jan 26 - Jan 27
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
1 bedroom, free WiFi, bed sheets

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
New Milford
8.0 out of 10, Very Good, (1 review)
"We camped at Freedom Farm and enjoyed the secluded woods setting for our tent. Everything was clean and well prepared for our stay, and the hosts were friendly and helpful. It is beautifully situated and is a short drive from some excellent hiking and biking in nearby state parks. I think a couple of things, though, could be improved. The tent was set up on an incline, which made sleeping a bit less comfortable than it might have been. I would recommend that the hosts build a level platform...
United States
Eric
The price is ￥23,355
￥29,972 total
includes taxes & fees
Jan 26 - Jan 27
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
Fridge, microwave, oven, stovetop

"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is ￥31,389
￥89,759 total
includes taxes & fees
Jan 26 - Jan 27
"Country outside the city " 3 bedrooms 2 full bathrooms
TV, fireplace, books

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
The price is ￥19,839
￥66,354 total
includes taxes & fees
Feb 1 - Feb 2
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Dining

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
New Fairfield
10.0 out of 10, Exceptional, (18 reviews)
"Great location and condition. Roome enough for everyone."
United States
Christopher H.
The price is ￥24,383
￥71,014 total
includes taxes & fees
Jan 27 - Jan 28
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
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

Hampton Inn Danbury

Hampton Inn Danbury

10/10 Excellent
"What can I say, everything was great down to the hot tub. Besides the pool, it was a bit cold I wosh the pool were a little warmer."
Johanna 2-night trip
Posted 2 days ago
Hampton Inn Danbury

Find out more about Roxbury

Search for holiday rentals in Roxbury on Expedia! You can easily find your home rentals, villas, holiday apartments in Roxbury using one of the methods below:

  • View our selection of featured holiday rentals in Roxbury
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  • Enter your travel dates to view the best deals on holiday rentals in Roxbury while they last

Look no further and take a look at our great range of rental properties in Roxbury!

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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?

Litchfield County Four Season Country Paradise: Visitors like this Roxbury vacation home rental. It is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Roxbury?

Choose from 16 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 Elephant's Trunk Flea Market.

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.