Roxbury Vacation Rentals

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In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Roxbury

Outdoor pool, a heated pool
Litchfield County Four Season Country Paradise

Vacation Home in Roxbury

9.6 out of 10, Exceptional, (50)
"Great time for all. Hosts were great."
United States
Ray S.
Litchfield County Four Season Country Paradise
Dining
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Vacation 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
Dining
Peaceful Vintage Home with Private Pond in Redding, CT.

Vacation 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.
$616 nightly
The price is $697
Dec 9 - Dec 10
Total with taxes and fees
Peaceful Vintage Home with Private Pond in Redding, CT.
Outdoor dining
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Vacation 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
Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Apartment in Cheshire

9.2 out of 10, Wonderful, (12)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Dining
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

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!
Property grounds
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Vacation Home in Danbury

10.0 out of 10, Exceptional, (24)
"Beautiful property with amazing lake views and water access."
United States
Sophia C.
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Exterior
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

Vacation 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!
Terrace/patio
Cozy Lakefront Bungalow w firepit/dock/kayaks

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

Cabin in Holmes

10.0 out of 10, Exceptional, (197)
"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!
Terrace/patio
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent

Vacation Home in Cornwall

9.6 out of 10, Exceptional, (53)
"Great house and great stay!"
United States
Timothy P.
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
Interior
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Vacation 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.
$174 nightly
The price is $197
Dec 7 - Dec 8
Total with taxes and fees
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Outdoor dining
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Vacation 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
Outdoor spa tub
Awesome Lake Home with tons of fun!

Vacation Home in New Fairfield

2.0 star property
9.8 out of 10, Exceptional, (7)
"Great spot "
United States
Mike P.
$677 nightly
The price is $767
Dec 9 - Dec 10
Total with taxes and fees
Awesome Lake Home with tons of fun!
Fridge, microwave, oven, stovetop
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Vacation Home in Carmel Hamlet

10.0 out of 10, Exceptional, (17)
"Fabulous property! Everything was as advertised with a great kitchen and grill. Tastefully decorated and comfortable. Great game room! "
United States
Rachel F.
$856 nightly
The price is $928
Dec 27 - Dec 28
Total with taxes and fees
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Outdoor dining
The Goshen Glass Chalet

Vacation 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
Exterior
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

Vacation 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
Outdoor dining
Candlewood Lake Retreat; Dock, Game Room & Firepit

Vacation 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
Pool
Charming 1870 cape cottage in Litchfield

Vacation Home in Litchfield

10.0 out of 10, Exceptional, (66)
"Beautiful home with everything you could possibly need for a vacation. Welcoming and very kind and helpful hosts. Lovely place for a family vacation. "
United States
Susanna Z.
Charming 1870 cape cottage in Litchfield
Exterior
New One Bedroom Apartment Centrally Located in Southbury

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
$110 nightly
The price is $124
Dec 5 - Dec 6
Total with taxes and fees
New One Bedroom Apartment Centrally Located in Southbury
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

Comfort Inn & Suites Danbury-Bethel

Comfort Inn & Suites Danbury-Bethel

10/10 Excellent
"Clean room,staff we great"
Sammie 2-night trip
Posted 2 days ago
Comfort Inn & Suites Danbury-Bethel

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 $124 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 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.