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

Holiday Homes in Sharon

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Sharon holiday homes

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

1. 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, (3 reviews)
"I really enjoyed my four night stay here."
United States
Jim B.
Cozy private room in a shared home with a Full-size bed and private bathroom.
A covered outdoor deck with wicker furniture, a grill, and a view of a lake.

2. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A wooden cabin interior with a bench, a rug, and a hanging plant.

3. 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, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is €173
includes taxes & fees
8 Nov - 9 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A modern kitchen with white cabinets, a large island, and a skylight.

4. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (15 reviews)
"Stayed with a group for Millbrook Horse Trials, we had an amazing weekend at this calm and relaxing home with plenty of beds and amenities! What a treat!"
United States
Marianne R.
The price is €1,245
includes taxes & fees
3 Nov - 4 Nov
A Country Lodge Straight Out of the Pages of a Great Novel
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

5. 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 €593
includes taxes & fees
3 Nov - 4 Nov
Chic Barn Style * Fireplace * Near Stissing House
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

6. The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.8 out of 10, Exceptional, (13 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
The George is an elegant restored home in the Hudson Valley
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

7. 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, (8 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 €659
includes taxes & fees
8 Nov - 9 Nov
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A hot tub in a backyard with a house, trees, and a clear sky.

8. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is €3,141
includes taxes & fees
30 Nov - 1 Dec
Las Flores Villa
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

9. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is €369
includes taxes & fees
3 Nov - 4 Nov
Cheerful 3-bedroom cottage with woodstove
A living room with a white sectional sofa, a dining area with a wooden table and chairs, and a staircase leading to an upper level.

10. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
New Milford
10.0 out of 10, Exceptional, (1 review)
"Perfect!!"
United States
Jeni O.
The price is €740
includes taxes & fees
1 Dec - 2 Dec
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
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

Prospect Berkshires

Prospect Berkshires

10/10 Excellent
"A brief overnight stay for us, so we didn’t get a chance to use the amenities, but the lakeside cabins were very comfortable with a beautiful view. All the members of the staff were very professional and welcoming."
SABELLE 1-night trip
Posted 2 hours ago
Prospect Berkshires

Find out more about Sharon

Sharon Holiday Homes information

Number of reviews
90
Accommodation
269 Holiday Homes
Lowest Price
€173
Highest Price
€3,141