Roxbury Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Roxbury

Holiday Home in Roxbury

9.6 out of 10, Exceptional, (50)
"As advertised, easy place to hang with friends. "
United States
Matthew H.
Litchfield County Four Season Country Paradise

Holiday Home in Brookfield

9.6 out of 10, Exceptional, (4)
"The host was very kind and welcoming. The home was spacious and the perfect setting for our celebration weekend. Everyone had their own space and we had multiple spaces for group activities. We enjoyed our time and appreciate the hospitality. "
United States
Valerie V.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Holiday Home in Redding

2.0 star property
10.0 out of 10, Exceptional, (2)
"Several of us stayed for one night for our kids soccer tournament. The home was spacious and had all the amenities needed to make our short stay comfortable. The host was very responsive and accommodating. "
United States
Annette H.
The price is AU$1,188
includes taxes & fees
30 Nov - 1 Dec
Peaceful Vintage Home with Private Pond in Redding, CT.

Cabin in Northwest Harwinton

8.6 out of 10, Excellent, (27)
"Love the place.. very clean ..loved the neighbors.. got to catch up on well needed rest.. the neighbors on the right were wonderful than the owners came and they were also wonderful also"
United States
Andrea m.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Holiday Home in New Fairfield

9.2 out of 10, Wonderful, (34)
"Amazing beautiful place!! Everything clean!! Definitely going to come back! "
United States
Andrew E.
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Apartment in Southbury

9.8 out of 10, Exceptional, (19)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is AU$202
includes taxes & fees
4 Dec - 5 Dec
New One Bedroom Apartment Centrally Located in Southbury

Holiday Home in Plymouth

9.8 out of 10, Exceptional, (39)
"Owners were there, helpful, all in all very good"
United States
Walter B.
Cozy Lakefront Bungalow w firepit/dock/kayaks

Cabin in Holmes

10.0 out of 10, Exceptional, (196)
"Great place to get away. Absolutely recommend it. "
United States
Demian B.
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Holiday Home in Danbury

10.0 out of 10, Exceptional, (24)
"We enjoyed a fantastic vacation and the house had amazing views that were fabulous. Plenty of activities for children & adults and the boat rides capped off a perfect week! Sorry to see the week end. "
United States
Jack O.
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Holiday Home in New Fairfield

10.0 out of 10, Exceptional, (80)
"Beautiful fun home, great owner!"
United States
Robin B.
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

Apartment in New Fairfield

10.0 out of 10, Exceptional, (34)
"Beautiful apartment in a beautiful setting. "
United States
Lisa
The price is AU$703
includes taxes & fees
1 Dec - 2 Dec
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Apartment in Cheshire

9.2 out of 10, Wonderful, (11)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is AU$256
includes taxes & fees
3 Dec - 4 Dec
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Holiday Home in Shelton

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."
United States
Alex C.
The price is AU$308
includes taxes & fees
26 Nov - 27 Nov
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Holiday Home in New Fairfield

9.8 out of 10, Exceptional, (35)
"Perfect location, well equipped from decks and dock, kayaks and fire pit. Beautiful well kept landscape. Nice open floor plan for family gatherings."
United States
Brian W.
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Holiday Home in New Fairfield

2.0 star property
9.6 out of 10, Exceptional, (5)
"Great spot "
United States
Mike P.
The price is AU$1,198
includes taxes & fees
30 Nov - 1 Dec
Awesome Lake Home with tons of fun!

Holiday Home in Carmel Hamlet

10.0 out of 10, Exceptional, (17)
"We had a great stay and had everything we needed!"
United States
Maueen Q.
The price is AU$1,530
includes taxes & fees
1 Dec - 2 Dec
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Holiday Home in Goshen

9.6 out of 10, Exceptional, (41)
"The place was very nice met all of our expectations. "
United States
Marie G.
The Goshen Glass Chalet

Cabin in Woodbury

10.0 out of 10, Exceptional, (1)
"My wife and I decided at the last minute to get away this place fit this it is a closed up ski resort the owner is so nice he actually came out went over everything with us the night we arrived the stay was amazing wood stove was the best we made a pallet on floor by the wood stove was just the best Seymour was the best and did everything to make your stay the best"
United States
Edward B.
Cozy 3-bedroom cabin in Woodbury. With Brook and mountain to enjoy.

Holiday Home in Watertown

9.6 out of 10, Exceptional, (16)
"It was a great time. Loved it hear would come back again. Owner was very helpful."
United States
Nosa I.
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

Holiday Home in New Milford

10.0 out of 10, Exceptional, (49)
"Everything was great! Thank you!"
United States
Ari W.
Candlewood Lake Retreat; Dock, Game Room & Firepit
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.

Black Friday Sale

Save up to 40% on select hotels
Save an average of 15% on thousands of hotels when you're signed in

Top Roxbury Hotel Reviews

Find out more about Roxbury

Everything you need to know about Roxbury holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Roxbury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Roxbury holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Roxbury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Roxbury holiday rentals we have selected for you start as low as AU$202 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Roxbury rentals

At Expedia, we put the best Roxbury holiday 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 holiday.

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. 

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 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 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.