Roxbury Vacation Rentals

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Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for Roxbury vacation rentals

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.
$109 nightly
The price is $122
Feb 20 - Feb 21
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (23 reviews)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
$107 nightly
The price is $121
Feb 19 - Feb 20
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
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.
$290 nightly
The price is $331
Feb 19 - Feb 20
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Interior

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.
$203 nightly
The price is $230
Feb 19 - Feb 20
Total with taxes and fees
Private Apartment in Southbury 102
Smart TV

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.4 out of 10, Exceptional, (16 reviews)
"Great Location - all the amenities you need for a nice restful stay. Did not have to reach-out to the host at all during our stay. "
United States
Robert S.
$149 nightly
The price is $168
Mar 1 - Mar 2
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
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.
$203 nightly
The price is $230
Mar 2 - Mar 3
Total with taxes and fees
Private Apartment in Southbury 103
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.
$174 nightly
The price is $197
Feb 19 - Feb 20
Total with taxes and fees
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Interior

Cozy & Serene Cabin with Fireplace, Ski Nearby!

Cozy & Serene Cabin with Fireplace, Ski Nearby!
Bethlehem
10.0 out of 10, Exceptional, (39 reviews)
"Very comfortable property. The host had thought of everything!"
United States
Jennifer Y.
$372 nightly
The price is $422
Feb 19 - Feb 20
Total with taxes and fees
Cozy & Serene Cabin with Fireplace, Ski Nearby!
Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.6 out of 10, Exceptional, (4 reviews)
"The cabin was perfect. Had everything we needed and clear directions. "
United States
Jocelyn L.
$172 nightly
The price is $195
Feb 19 - Feb 20
Total with taxes and fees
Hoppy Hill Farm House
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
$406 nightly
The price is $467
Feb 19 - Feb 20
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
1 bedroom, desk, iron/ironing board, WiFi

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
$334 nightly
The price is $384
Feb 19 - Feb 20
Total with taxes and fees
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
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.
$331 nightly
The price is $381
Mar 2 - Mar 3
Total with taxes and fees
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
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.
$211 nightly
The price is $240
Mar 1 - Mar 2
Total with taxes and fees
Private Apartment in Southbury 101
Desk, WiFi

#43- Modern Luxury Log Cabin Retreat | Fire Pit

#43- Modern Luxury Log Cabin Retreat | Fire Pit
Prospect
$399 nightly
The price is $426
Feb 19 - Feb 20
Total with taxes and fees
#43- Modern Luxury Log Cabin Retreat | Fire Pit
Outdoor pool

Cozy 1-bedroom apartment in lovely Oxford

Cozy 1-bedroom apartment in lovely Oxford
Oxford
10.0 out of 10, Exceptional, (1 review)
"I made a late reservation, and my host, Jackie, was always accommodating, welcoming, and in regular communication with me. The amenities were just what I needed, right down to the coffee pod and snack selection! The apartment is well laid out, as if I were walking into my own home, convenient to shopping and friends.Thank you, Jackie!"
United States
LIsa G.
$142 nightly
The price is $160
Feb 19 - Feb 20
Total with taxes and fees
Cozy 1-bedroom apartment in lovely Oxford
Fridge, microwave, oven, stovetop

Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
$203 nightly
The price is $230
Mar 2 - Mar 3
Total with taxes and fees
Private Apartment in Southbury 104
Pool

Cozy In-law Garden Suite in Colonial Home

Cozy In-law Garden Suite in Colonial Home
Redding
$148 nightly
The price is $167
Feb 19 - Feb 20
Total with taxes and fees
Cozy In-law Garden Suite in Colonial Home
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
$342 nightly
The price is $389
Feb 28 - Mar 1
Total with taxes and fees
Litchfield Retreat, Wineries, Foliage & Skiing
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, (13 reviews)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
$328 nightly
The price is $355
Feb 19 - Feb 20
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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
$189 nightly
The price is $214
Feb 22 - Feb 23
Total with taxes and fees
The Perch in the Purchase -- Cozy, unique, and private
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

10/10 Excellent
"Everything was great"
Glenn 1-night trip
Posted 1 day 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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Roxbury in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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 Quassy Amusement Park, or get out into nature at a spot like Lake Lillinonah. In the larger area, you’ll find Steep Rock Preserve and Glebe House Museum and The Gertrude Jekyll Garden.

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.