Roxbury Holiday Rentals

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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Roxbury holiday rentals

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 HK$1,723
HK$3,992 total
includes taxes & fees
1 Apr - 2 Apr
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
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 HK$713
HK$977 total
includes taxes & fees
1 May - 2 May
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, (24 reviews)
"Excellent host."
United States
David
The price is HK$729
HK$996 total
includes taxes & fees
4 Apr - 5 Apr
Cozy One Bedroom Apartment Centrally Located in Southbury
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.
The price is HK$1,586
HK$3,119 total
includes taxes & fees
2 Apr - 3 Apr
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is HK$2,044
HK$3,099 total
includes taxes & fees
4 Apr - 5 Apr
Litchfield Retreat, Wineries, Foliage & Skiing
Fridge, microwave, oven, stovetop

Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
10.0 out of 10, Exceptional, (3 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 HK$740
HK$1,774 total
includes taxes & fees
1 Apr - 2 Apr
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
9.4 out of 10, Exceptional, (17 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.
The price is HK$893
HK$1,544 total
includes taxes & fees
19 Apr - 20 Apr
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Smart TV, fireplace, books

Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is HK$1,527
HK$1,937 total
includes taxes & fees
1 Apr - 2 Apr
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Fridge, microwave, oven, stovetop

The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"The place was absolutely spotless and magnificent in every way. Highly recommended."
United States
Robert A.
The price is HK$2,284
HK$2,918 total
includes taxes & fees
2 Apr - 3 Apr
The Jefferson Guest House, Spacious, Special Views
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 HK$1,057
HK$1,688 total
includes taxes & fees
7 Apr - 8 Apr
The Perch in the Purchase -- Cozy, unique, and private
Interior

Dainty New Preston Cottage w/ Dock & Lake Views!

Dainty New Preston Cottage w/ Dock & Lake Views!
3.0 star property
New Preston
The price is HK$1,676
HK$4,049 total
includes taxes & fees
15 Apr - 16 Apr
Dainty New Preston Cottage w/ Dock & Lake Views!
Exterior detail

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
New Fairfield
10.0 out of 10, Exceptional, (35 reviews)
"Stunning property!!"
United States
Samantha
The price is HK$2,154
HK$3,754 total
includes taxes & fees
1 Apr - 2 Apr
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
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 HK$754
HK$1,790 total
includes taxes & fees
1 Apr - 2 Apr
Private Apartment in Southbury 101
Room

Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
The price is HK$840
HK$2,986 total
includes taxes & fees
7 Apr - 8 Apr
Art House 3 Beds Close to Warner Theater
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 HK$1,946
HK$4,965 total
includes taxes & fees
6 Apr - 7 Apr
"Country outside the city " 3 bedrooms 2 full bathrooms
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 HK$707
HK$2,688 total
includes taxes & fees
7 Apr - 8 Apr
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
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 HK$1,012
HK$3,142 total
includes taxes & fees
5 Apr - 6 Apr
Cozy Modern Farmhouse Private Apt - 3 Beds
Cookware/dishes/utensils

Awesome Lake Home with tons of fun!

Awesome Lake Home with tons of fun!
New Fairfield
9.8 out of 10, Exceptional, (7 reviews)
"Great spot "
United States
Mike P.
The price is HK$3,172
HK$5,555 total
includes taxes & fees
6 Apr - 7 Apr
Awesome Lake Home with tons of fun!
Outdoor pool

Cozy 1-bedroom apartment in lovely Oxford

Cozy 1-bedroom apartment in lovely Oxford
Oxford
10.0 out of 10, Exceptional, (4 reviews)
"This was my second time staying here. The apartment was immaculately clean and the owner was both professional and personal! The apartment had all the comforts of home, from coffee and snacks in the kitchen to self-care items (e.g., toothbrush, toothpaste, etc). Truly a hidden gem, close to shopping, restaurants, and highways! "
United States
LIsa G.
The price is HK$877
HK$1,256 total
includes taxes & fees
1 Apr - 2 Apr
Cozy 1-bedroom apartment in lovely Oxford
Smart TV, fireplace, video games, DVD player

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

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Carmel Hamlet
10.0 out of 10, Exceptional, (19 reviews)
"We had a great stay and had everything we needed!"
United States
Maueen Q.
The price is HK$4,222
HK$7,657 total
includes taxes & fees
7 Apr - 8 Apr
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
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

Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

10/10 Excellent
"Slightly expensive but overall good"
Muhammad 1-night trip
Posted 8 hours ago
Hilton Garden Inn Shelton

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!

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 Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Roxbury offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Roxbury?

Choose from 16 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 Lovers Leap State Park.

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.