A covered bridge labeled "West Cornwall" with a sign indicating a height restriction of 10-11 inches and a one-lane bridge warning.

Sharon Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Sharon holiday rentals

A living room with a fireplace, two armchairs, a sofa, and a TV.

1. 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, (24 reviews)
"Very nice, great location in town"
United States
Lisa F.
The price is HK$1,300
HK$1,652 total
includes taxes & fees
1 Oct - 2 Oct
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A two-story house with a front porch, a small balcony, and a white picket fence.

2. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.4 out of 10, Exceptional, (6 reviews)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is HK$659
HK$2,560 total
includes taxes & fees
29 Sept - 30 Sept
Cozy Attic 10 min to Llitchfield
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

3. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is HK$1,458
HK$5,011 total
includes taxes & fees
28 Sept - 29 Sept
Chic Barn Style * Fireplace * Near Stissing House
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

4. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (52 reviews)
"Quaint very nice loved the space very cozy the hot tub was a nice touch I did use that a few times helped my sore back LOL everything went as expected I would stay here again"
United States
paul
The price is HK$988
HK$1,835 total
includes taxes & fees
28 Sept - 29 Sept
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A two-story house with a front porch, a small balcony, and a white picket fence.

5. 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$1,013
HK$3,037 total
includes taxes & fees
28 Sept - 29 Sept
Cozy Modern Farmhouse Private Apt - 3 Beds
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

6. Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (6 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is HK$3,005
HK$4,850 total
includes taxes & fees
18 Oct - 19 Oct
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A wooden cabin interior with a bench, a rug, and a hanging plant.

7. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is HK$974
HK$1,728 total
includes taxes & fees
4 Oct - 5 Oct
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

8. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (21 reviews)
"It was great!"
United States
Amanda T.
The price is HK$1,259
HK$2,101 total
includes taxes & fees
28 Sept - 29 Sept
Pristine Cozy Walkable Downtown 2BR Getaway
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

9. Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is HK$1,073
HK$3,174 total
includes taxes & fees
30 Sept - 1 Oct
Art House 3 Beds Close to Warner Theater
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

10. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is HK$3,530
HK$5,129 total
includes taxes & fees
1 Oct - 2 Oct
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A wooden cabin with a porch, a grill, and a flower planter.

11. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
The price is HK$1,569
HK$2,811 total
includes taxes & fees
28 Sept - 29 Sept
Ideal location for summer and winter activities with plenty of outdoor space.
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

12. Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (8 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
The price is HK$1,351
HK$1,723 total
includes taxes & fees
28 Sept - 29 Sept
Hudson Valley Farm Getaway- West/Llama Lover Lane
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

13. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,461
HK$3,245 total
includes taxes & fees
12 Oct - 13 Oct
Cheerful 3-bedroom cottage with woodstove
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

14. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is HK$1,177
HK$1,494 total
includes taxes & fees
28 Sept - 29 Sept
The Brooks Motel: Exceptional Suite
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

15. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (17 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is HK$1,686
HK$2,096 total
includes taxes & fees
28 Sept - 29 Sept
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A white house with a steeply pitched roof and a small tower-like structure.

16. Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
9.8 out of 10, Exceptional, (6 reviews)
"Lovely home in the heart of Millbrook."
United States
Marianne A S.
The price is HK$2,510
HK$3,638 total
includes taxes & fees
28 Sept - 29 Sept
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A rustic cabin surrounded by a forest with a stream in the foreground.

17. Creek Side Cabin with Wood Fired Hot Tub and Fire Pit

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"Great little house, our favorite part was the gorgeous creek. Absolutely would recommend to pet lovers and those looking for peaceful nature :)"
United States
Kristine W.
The price is HK$2,434
HK$4,146 total
includes taxes & fees
29 Sept - 30 Sept
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

18. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
10.0 out of 10, Exceptional, (1 review)
"Clean and close to activitys"
United States
randall
The price is HK$635
HK$1,248 total
includes taxes & fees
13 Oct - 14 Oct
Cozy private room in a shared home with a Full-size bed and private bathroom.
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

19. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (6 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is HK$3,138
HK$6,185 total
includes taxes & fees
4 Oct - 5 Oct
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

20. Escape to Bantam Lake- With Fireplace and Hot tub!

Escape to Bantam Lake- With Fireplace and Hot tub!
Morris
10.0 out of 10, Exceptional, (4 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
United States
Shannon M.
The price is HK$2,275
HK$4,212 total
includes taxes & fees
5 Oct - 6 Oct
Escape to Bantam Lake- With Fireplace and Hot tub!
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 Sharon Hotel Reviews

The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"The personell at the Inn were excellent, couldn't do enough for you. The room was clean and well maintained. The breakfast was great!!"
Kenneth 1-night trip
Posted 8 hours ago
The Litchfield Inn

Find out more about Sharon

Search for holiday rentals in Sharon on Expedia! You can easily find your home rentals, villas, holiday apartments in Sharon using one of the methods below:

  • View our selection of featured holiday rentals in Sharon
  • Use the map to find apartments and other holiday homes in the Sharon neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sharon while they last

Look no further and take a look at our great range of rental properties in Sharon!

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?

Well laid out 2-bedroom private home in Washington-close to the green and depot: This holiday home rental outside of Sharon offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave. Make the most of garden in this rental home to help you unwind.

How many holiday rentals will I find in Sharon?

Expedia has 14 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, Macedonia Brook State Park and Veterans Field 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.