Sharon Holiday Rentals

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Holiday Rentals in Sharon

Sharon Country Estate On 300 Acres With 100 Mile Views
9.6 out of 10, Exceptional, (49)
"Beautiful antique home!! Would love to return!"
The price is NZ$799
includes taxes & fees
1 Jun - 2 Jun
Sharon Country Estate On 300 Acres With 100 Mile Views
Idillic summer getaway in Litchfield Hills, CT.
10.0 out of 10, Exceptional, (11)
"Came here for a birthday getaway filled with hiking, and great restaurants! It rained the entire time, but this beautiful cottage was so relaxing, with the windows overlooking the private backyard, we simply sat and read and watched the rain roll by. Lots of room, spacious bedrooms. Great for a family."
Idillic summer getaway in Litchfield Hills, CT.
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, (75)
"We had such an awesome stay! Check in process was easy! Amazing scenery amazing adventure we had with our two furr babies!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
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Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, (58)
"Property manager was very kind and responsive. Greatly enjoyed the views of the pond and the basement pool and ping pong tables. Great time playing these games with mybson as the weather wasn't conducive for water activities."
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, (28)
"For a woodsy getaway close to real highways, here’s your spot. A good home base for local activities. Cute not chic, clean and functional. Chickens and goats on the property added a great farm with no work charm."
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, (8)
"We’d go back."
The price is NZ$748
includes taxes & fees
4 Jun - 5 Jun
Cozy & Chic Cabin by the Lake, with access to private Beach!
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, (70)
"Fantastic, loved everytbing about it"
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (74)
"For the groomsman it was perfect crazy fun."
Spectacular Short Term Vacation Rental in Kent
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is NZ$444
includes taxes & fees
24 Jun - 25 Jun
Perfect Vacation Get Away - Historical New Marlborough
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, (7)
"We had a great stay while skiing for 2 days at nearby Catamount ski resort. The kitchen and house were fully stocked with all essentials. Netflix access enabled us to enjoy a family movie after a long day of skiing. Cozy house and quiet area.......nice to wake up to hear birds chirping!!"
The price is NZ$545
includes taxes & fees
30 Jun - 1 Jul
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
10.0 out of 10, Exceptional, (127)
"We thoroughly enjoyed our stay at Joe and Lisa’s stunning barn. It is rammed full of character and is very well located to explore both the Hudson Valley and the Berkshires, just over the border in MA. Joe left us to enjoy the place in peace but was always on hand to answer any questions. The kids really enjoyed taking a dip in the hot tub and making s’mores over the outdoor fire pit. We will definitely return!"
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
The Long View of Candlewood Lake
9.8 out of 10, Exceptional, (7)
"It was such a nice property and the host was amazing"
The Long View of Candlewood Lake
Waterview Home in the Berkshires: Near Hiking
9.2 out of 10, Wonderful, (14)
"Lovely house and kind owner. We had a great time. The view is amazing."
Waterview Home in the Berkshires: Near Hiking
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, (7)
"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
Peaceful, Post and Beam Loft, Sleeps 9
10.0 out of 10, Exceptional, (8)
"beautifully stay for couples."
Peaceful, Post and Beam Loft, Sleeps 9
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (80)
"We have 20 years experience renting homes for family gatherings and this is the most interesting and amazing property. Gardens galore, plenty of space to congregate or go off by yourself, fully appointed kitchen, and comfortable space. We were a party of ten and everyone loved the experience."
Antique Farmhouse Totally Restored
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
9.4 out of 10, Exceptional, (33)
"Very positive."
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Newly Renovated Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (19)
"The house was perfect for accommodating a large group of friends for a nice, relaxing break froze reality! It gave us space for cooking meals, playing games, and lounge around. The lake was perfect for a refreshing dip! It was overall an amazing experience!"
Newly Renovated Family House On Highland Lake with Dock
The Nest at The Granary
10.0 out of 10, Exceptional, (23)
"The Nest is so close to everything. Walked in and the place is so clean. Like no one has ever stayed there before. Cass was super responsive (within minutes of messaging him I had a response). Checked in with us to ensure we were enjoying our stay. Our next visit to the area, we will be staying there again. Best place in town for sure. Tip: Enter the front door code to the lobby super fast. That thing is a little temperamental. Side note: Check out Theo’s restaurant for breakfast."
The Nest at The Granary
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See all available properties in Sharon
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.

Other types of properties in Sharon you may be interested in

Sharon Country Estate On 300 Acres With 100 Mile Views
9.6 out of 10, Exceptional, (49)
"Beautiful antique home!! Would love to return!"
The price is NZ$799
includes taxes & fees
1 Jun - 2 Jun
Sharon Country Estate On 300 Acres With 100 Mile Views
Idillic summer getaway in Litchfield Hills, CT.
10.0 out of 10, Exceptional, (11)
"Came here for a birthday getaway filled with hiking, and great restaurants! It rained the entire time, but this beautiful cottage was so relaxing, with the windows overlooking the private backyard, we simply sat and read and watched the rain roll by. Lots of room, spacious bedrooms. Great for a family."
Idillic summer getaway in Litchfield Hills, CT.
Rocky River Inn
3.0 star property
8.4 out of 10, Very good, (479)
"This place was very cute and clean. "
The price is NZ$186
includes taxes & fees
1 Jul - 2 Jul
Rocky River Inn
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Sharon holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Sharon. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Sharon. Seeing all the best attractions is bound to make you fall in love with Sharon. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Sharon short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Sharon?

Yes, there are holiday rentals close to the most popular sights in Sharon, or you can select a more secluded option if you're looking for a relaxing stay. Sharon is known for its forests and golf courses.

What are some of the best holiday rentals that Sharon has to offer?

Sharon Country Estate On 300 Acres With 100 Mile Views: This highly rated holiday home rental in Sharon is located on a lake, and offers a garden, air conditioning and laundry facilities 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.

How many holiday rentals will I find in Sharon?

Expedia has 13 holiday rentals for your stay in Sharon.

What’s there to see and do in Sharon?

Enjoy the outdoors at Kent Falls State Park and Housatonic River, or simply take in cultural attractions like TriArts Sharon Playhouse and Bodhi Tree Gallery. While here, Housatonic Meadows State Park and Macedonia Brook State Park are other places worth a visit.

What’s a holiday rental in Sharon like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sharon. Holiday rentals feature extras such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy 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 choice for small groups.

Recent reviews of Sharon properties
Expedia verified reviews