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Roxbury Vacation Rentals

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Vacation Rentals in Roxbury

Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Beach nearby, beach towels
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, 76 reviews
"Perfect weather for a getaway! Great location to get to get around. Cottage was perfect for us. Fire pit was great to hang out at. Went kayaking across the street. Beautiful lake. However, the access to the lake was a wee bit steep but we are in shape to handle it. All in all it was a great time!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
On the beach, sun loungers
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, 59 reviews
"We had a lovely weekend stay for a quick family get-away. The main kitchen and living area has spectacular views onto the lake as does the deck where we spent most of our time. The lake is just across the very quiet street. The kitchen is incredibly well stocked, the host super responsive and the rooms very comfortable. We did not use the well equipped basement work-out and additional TV space but it looked great. Easy to get to grocery store, hikes, local attractions but honestly we just loved...
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Property grounds
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
10.0 out of 10, Exceptional, 170 reviews
"What a great long weekend we had! Being on the lake, looking at the lake, bbq-ing with a view of the lake - it was all lake, all the time, which is exactly what we wanted. Plus we got perfect weather. Cabin is adorable and beds are comfortable, too."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Property grounds
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
9.8 out of 10, Exceptional, 19 reviews
"Our family enjoyed our stay at the Cottage during our recent visit to CT for our son's college graduation. The views of the lake from the living room, the deck and the patio with fire pit are great and very peaceful. The kitchen was nicely outfitted with everything needed to cook and prepare meals. The only drawback was that there were no closets or chest of drawers in the (2) basement bedrooms. There was no place to unpack and hang our clothes for the 4 days we were there; the only closet was...
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
Property grounds
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
10.0 out of 10, Exceptional, 6 reviews
"Great property, very clean and host was quick to reply. We were impressed with the amenities available (most places don’t have detergent, etc) and the view was amazing! We didn’t have time to go to the dock but it looked very nice! Wish we had time to stay longer. We will definitely try to stay there again for our next family event"
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
Spectacular Short Term Vacation Rental in Kent
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, 74 reviews
"For the groomsman it was perfect crazy fun."
Spectacular Short Term Vacation Rental in Kent
Cozy & Chic Cabin by the Lake, with access to private Beach!
Exterior
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, 8 reviews
"We’d go back."
The price is $250
$489 total
includes taxes & fees
Jul 1 - Jul 2
Cozy & Chic Cabin by the Lake, with access to private Beach!
Beautiful cozy rooms near hospital and down town area
Private kitchen | Fridge, microwave, oven, stovetop
Beautiful cozy rooms near hospital and down town area
8.4 out of 10, Very Good, 10 reviews
"People were very nice and welcoming. Area looks questionable but the place itself is very comfortable, clean and enjoyable."
The price is $109
$246 total
includes taxes & fees
Jun 18 - Jun 19
Beautiful cozy rooms near hospital and down town area
Guest Cottage on Country Estate
Property grounds
Guest Cottage on Country Estate
9.2 out of 10, Wonderful, 33 reviews
"My husband and son stayed here for 5 days. They had a fabulous time hiking in the state park nearby. Thanks for a great stay!"
Guest Cottage on Country Estate
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Property grounds
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
9.8 out of 10, Exceptional, 21 reviews
"The property was as described and the living space was perfect for our visit. The deck and views are amazing. If staying at this property, you just need to be aware that it is very difficult getting luggage and groceries into the property. You have to go down a long flight of stairs, walk down a very steep driveway and then go down another flight of stairs. Once you are in, bedroom access requires that you go up or down additional stairs."
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Smart TV, fireplace, table tennis, stereo
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
10.0 out of 10, Exceptional, 11 reviews
"We absolutely loved the house! This was the perfect place to bring my adult children together for a weekend away. The rooms were beautiful, beds were super comfortable, and house nicely decorated. There were spots for smaller groups to sit together and hang out or to come together and chat. The hot tub was appealing to my 20somethings but it was rainy- next time!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Lakeview Estate - Chef's Kitchen - NYC Getaway
Outdoor dining
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, 18 reviews
"Beautiful, spacious property with all the amenities we needed and more. I would recommend and we will certainly return!"
The price is $733
$1,300 total
includes taxes & fees
Jul 2 - Jul 3
Lakeview Estate - Chef's Kitchen - NYC Getaway
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
3 bedrooms, iron/ironing board, WiFi, bed sheets
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, 1 review
"We went to the area to celebrate my husbands 30th birthday with some friends and absolutely loved the home. It was brand new and decorated immaculately. It comfortably fit our group and we thoroughly enjoyed our time there. The hosts were super accommodating and quick to respond. Would absolutely reccomend and go again!"
The price is $499
$916 total
includes taxes & fees
Jun 16 - Jun 17
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Candlewood Lake Retreat with year round views
Property grounds
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, 7 reviews
"We thoroughly enjoyed our time at this wonderful little home. It was pleasantly quiet and secluded, but was just minutes away from some wonderful restaurants and just a short walk to the lake. The hosts were just so responsive and accommodating. We also had one day of rainy weather, which afforded us the opportunity to simply stay in and relax. The kitchen had all of the amenities we could have asked for. The seating area on the deck was spacious and comfortable. We are certainly looking forward...
Candlewood Lake Retreat with year round views
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Exterior
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
10.0 out of 10, Exceptional, 72 reviews
"We stayed here for my friend's low-key bachelorette party. Peter was a great and responsive host, and the property was wonderful. We sang lots of karaoke and enjoyed cocktails on the large deck with beautiful views. Access to the community beach club was a big plus. Everyone had a great time and was really impressed with this property. Highly recommend it!"
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, 20 reviews
"We were in area from Uk visiting friends who live not far away. So this little home was just ideal for us. Weather improved on the day we left so we didnt sit outside by the lake but we did enjoy watching the birds and fish."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Peaceful apartment on 3.5 acres w/ artist studio.
Game room
Peaceful apartment on 3.5 acres w/ artist studio.
10.0 out of 10, Exceptional, 11 reviews
"Cute."
The price is $140
$213 total
includes taxes & fees
Jun 18 - Jun 19
Peaceful apartment on 3.5 acres w/ artist studio.
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Property grounds
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
10.0 out of 10, Exceptional, 17 reviews
"Gorgeous, as advertised!"
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Lakefront Home, Close to Mt Southington!
Fridge, microwave, stovetop, dishwasher
Lakefront Home, Close to Mt Southington!
10.0 out of 10, Exceptional, 7 reviews
"This is a charming house that actually is even better than the photos! Spotless and organized. Kitchen is perfectly stocked. Came with a bag of nice Italian coffee, Kurig and teas with refrigerated creamer. Bed was terrific and large. AC and Heat easy to use. Easy to find and surrounded by everything you need, like food, coffee, bagels, restaurants."
Lakefront Home, Close to Mt Southington!
Traveling Nurse or Business Professional
Exterior
Traveling Nurse or Business Professional
10.0 out of 10, Exceptional, 7 reviews
"The neighborhood was clean, upscale, and beautifully kept. It came with Candlewood Beach access. The second story suite was gorgeous, clean, and well apportioned. The bed was comfortable. The whole house was well maintained and a wonderful,"homey" feel to it. The Hostess was friendly, cheerful, and very accommodating. The house is on the hillside leading to Lake Candlewood. As can be imagined, the views from the windows were outstanding."
Traveling Nurse or Business Professional
Don't see what you're looking for?
See all available properties in Roxbury
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.

Roxbury Vacation Rental Travel Info

Number of vacation rentals
2
Popular accommodation
Roxbury private vacation homes
Known landmarks
Woodbury Ski Area, Lovers Leap State Park and Elephant's Trunk Flea Market
International airport
White Plains, NY (HPN-Westchester County)

Other types of properties in Roxbury you may be interested in

Courtyard by Marriott Waterbury Downtown
Lobby lounge
Courtyard by Marriott Waterbury Downtown
3.0 star property
8.2 out of 10, Very Good, 1,004 reviews
"Wish they had a pool .otherwise everythi g was fine.."
The price is $109
$125 total
includes taxes & fees
Jun 16 - Jun 17
Courtyard by Marriott Waterbury Downtown
Hilton Garden Inn Shelton
Terrace/patio
Hilton Garden Inn Shelton
3.0 star property
7.6 out of 10, Good, 1,007 reviews
"It was clean and our room was service every day. The facility was clean and near shopping center "
The price is $110
$126 total
includes taxes & fees
Jul 1 - Jul 2
Hilton Garden Inn Shelton
Hampton Inn by Hilton Shelton
Indoor pool
Hampton Inn by Hilton Shelton
2.5 star property
8.4 out of 10, Very Good, 1,006 reviews
"Very comfortable, staff is pleasant. Was perfect for a quick business trip."
The price is $113
$130 total
includes taxes & fees
Jun 23 - Jun 24
Hampton Inn by Hilton Shelton
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.

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 $109 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.

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?

Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond: Visitors like this Roxbury vacation home rental. It is located on the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Roxbury?

Choose from 18 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 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.

Recent reviews of Roxbury properties
Expedia verified reviews

Microtel Inn & Suites by Wyndham Bethel/Danbury

Microtel Inn & Suites by Wyndham Bethel/Danbury

5/5 Excellent
"I which this Hotel was Pet free."
A verified traveler stayed at Microtel Inn & Suites by Wyndham Bethel/Danbury
Posted 13 hours ago
Microtel Inn & Suites by Wyndham Bethel/Danbury