Sharon Vacation Rentals

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Oct 10 - Oct 12
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Vacation Rentals in Sharon

Our top choices for Sharon vacation rentals

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Dining

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

8.8 out of 10, Excellent, (24)
"The cabin was great! Exactly as described and pictured. The kitchen was well stocked with all the basic cooking instruments and utensils. We had a blast and would absolutely come back."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Be in Nature at this Gorgeous Riverfront Cabin
Smart TV, books

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (21)
"An ideal retreat. The modern cabin offered serene surroundings with stunning views of the woods and creek. The property was well-maintained, and the property manager was highly responsive. A perfect choice for a peaceful and refreshing getaway."
Be in Nature at this Gorgeous Riverfront Cabin
Guesthouse Cabin vacation rentals in Berkshire County
Dining

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is ￥54,468
￥101,731 total
includes taxes & fees
Sep 28 - Sep 29
Guesthouse Cabin vacation rentals in Berkshire County
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Fridge, microwave, oven, stovetop

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (55)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"Everything was great...and beautiful!"
The price is ￥29,522
￥59,688 total
includes taxes & fees
Sep 30 - Oct 1
The Blue Elm - A Historic Berkshire Cottage
Whispering Estate Guest House - A Romantic Countryside Getaway
Exterior detail

Whispering Estate Guest House - A Romantic Countryside Getaway

10.0 out of 10, Exceptional, (3)
"Beautiful property and great location. A true retreat. "
The price is ￥118,088
￥172,778 total
includes taxes & fees
Sep 25 - Sep 26
Whispering Estate Guest House - A Romantic Countryside Getaway
Summer Lake Cottage, private beach, Berkshire Hills, small village
Exterior

Summer Lake Cottage, private beach, Berkshire Hills, small village

9.4 out of 10, Exceptional, (82)
"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "
Summer Lake Cottage, private beach, Berkshire Hills, small village
Charming cottage with lake access, wood burning fire place, and WiFi
Smart TV, fireplace

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
9.0 out of 10, Wonderful, (8)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Exterior

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

9.8 out of 10, Exceptional, (20)
"We had a wonderful time, the property is lovely and the house is delightful."
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Stunning Light-Filled Contemporary Home on 7 Acres
Interior

Stunning Light-Filled Contemporary Home on 7 Acres

10.0 out of 10, Exceptional, (25)
"5-stars. Fantastic property, great communication with host. Perfect stay. Thank you!"
Stunning Light-Filled Contemporary Home on 7 Acres
Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (91)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Exterior

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

9.6 out of 10, Exceptional, (14)
"The house is huge with plenty of room and tons of features! Pool and hot tubs were lots of fun and the game room is full of games and tables to keep the kids happy.The location is very secluded and private, with easy access to stores and restaurants right down the street if needed.Brian was very responsive and easy to work with before and during our stay."
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
The Race Mountain House
Pool

The Race Mountain House

2.0 star property
9.2 out of 10, Wonderful, (5)
"I spent my 60th birthday with a few friends at Mountain House and it was even better than I dreamed. The comfort and simplicity of the decor along with the mountain views. A must for those who like simple elegance."
The Race Mountain House
Charming 2-bedroom apartment waterfront with WiFi, lovely New Milford
TV, fireplace

Charming 2-bedroom apartment waterfront with WiFi, lovely New Milford

10.0 out of 10, Exceptional, (4)
"This ground level apartment is comfortable and exceptionally clean, and above all its location in a bucolic setting made our two night stay peaceful and restful. Knowing location of the key made the check-in very easy, and the kitchen facilities met our needs. "
Charming 2-bedroom apartment waterfront with WiFi, lovely New Milford
Litchfield County Four Season Country Paradise
Outdoor pool, a heated pool

Litchfield County Four Season Country Paradise

9.6 out of 10, Exceptional, (50)
"Overall rating 5/5. I would recommend this home to other families and would stay again. "
Litchfield County Four Season Country Paradise
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!
Property grounds

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

10.0 out of 10, Exceptional, (126)
"A delightful place. Having the lake to ourselves with magnificent views plus a property that has plenty to keep everyone active--including the very active 4 year old in our group--was amazing. Do note that the downstairs bathroom has narrow doors so mobility impaired people may not be able to access it without assistance. "
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!
Treehouse With Outdoor Bathtub & Stream!
Exterior

Treehouse With Outdoor Bathtub & Stream!

10.0 out of 10, Exceptional, (2)
"Beautiful stay! Secluded and accommodations were lovely, just like in the pictures. Amazing to wake up with the view of the trees and the birds chirping all around. Would love to stay again. I would recommend planning your itinerary before arriving because the WiFi was a little spotty. "
Treehouse With Outdoor Bathtub & Stream!
Reset and Relax in Luxury Cottage
Property grounds

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (43)
"Perfect private retreat a mile from The Omega Institute. Clean and updated one bedroom, with friendly, helpful hosts!"
Reset and Relax in Luxury Cottage
The Goshen Glass Chalet
Outdoor dining

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (40)
"we couldn't ask for a better place. It had all the conveniences we like. The host did a great job here."
The Goshen Glass Chalet
Family House On Highland Lake with Dock
Fridge, microwave, oven, stovetop

Family House On Highland Lake with Dock

10.0 out of 10, Exceptional, (28)
"Awesome location, plenty of space in the house, clean, and the host was very responsive. Will definitely stay here again when in Connecticut. "
Family House On Highland Lake with Dock
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

it's a good thing

it's a good thing

10/10 Excellent
"Really sweet woman who owns the house. Gave us good recommendations for dinner and things to do. The room was really cozy and fall! "
Caitlin 2-night trip
Posted 3 days ago
it's a good thing

Find out more about Sharon

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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Sharon?

Yes, we have vacation rentals near well known points of interest in Sharon, or you can choose a secluded option if you'd like a relaxing place to stay. Sharon is known for its forests and golf courses.

What are some of the best vacation home rentals in Sharon?

Lakefront Fall Foliage in New England Just 2 Hours From NYC: This highly rated vacation home rental in Sharon is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a private yard and a selection of games.

How many vacation rentals will I find in Sharon?

Expedia has 12 vacation 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 vacation rental in Sharon like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Sharon. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for families.