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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Sharon Vacation Homes

Spacious Home nestled along the Blackberry River in Northwest CT
Enjoy cooking and dining in this well-equipped kitchen with a central island, appliances, and a dining area that opens to a deck with a grill.

Spacious Home nestled along the Blackberry River in Northwest CT

10.0 out of 10, Exceptional, (86)
"The team stayed here for a curling tournament. Great location for that and perfect for 4 non-couple guests"
Spacious Home nestled along the Blackberry River in Northwest CT
Charming cottage with lake access, wood burning fire place, and WiFi
Relax in this inviting living room with a sofa, dresser, and small table.

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

2.0 star property
9.0 out of 10, Wonderful, (7)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi
Lake Oasis with Firepit, Game room and Kayaks
Smart TV, table tennis

Lake Oasis with Firepit, Game room and Kayaks

10.0 out of 10, Exceptional, (1)
"This was our family's first time to Candlewood Lake/Squantz Pond. The area is picturesque and the location of this property is perfect. The porch off of the living area directly overlooks Squantz Pond and mountains. The basement was ideal for teenagers with a projector screen, air hockey/pool, and exercise equipment. The bedroom were spacious and beds comfortable. The kitchen/living area are open concept and the whole family could be together. The owner and his daughter are incredibly kind and...
Lake Oasis with Firepit, Game room and Kayaks
Tranquil Litchfield Connecticut Retreat".
Relax by the fire pit in a serene outdoor seating area surrounded by Adirondack chairs.

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (15)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
The price is CA $310
CA $440 total
includes taxes & fees
Aug 10 - Aug 11
Tranquil Litchfield Connecticut Retreat".
Private Annex/Former Artist Studio
Relax on the deck overlooking a lush garden with a tranquil atmosphere.

Private Annex/Former Artist Studio

10.0 out of 10, Exceptional, (51)
"Great property great location wonderful day"
Private Annex/Former Artist Studio
Taconic Hideaway – Swimming, BBQ Pit, Hiking
Relax on the deck surrounded by trees, with Adirondack chairs and a small table for a peaceful retreat.

Taconic Hideaway – Swimming, BBQ Pit, Hiking

2.0 star property
10.0 out of 10, Exceptional, (6)
"Great stay. The host was great with communicating directions and details for the home and even shared local recommendations. We appreciated their quick response to our questions, too. "
Taconic Hideaway – Swimming, BBQ Pit, Hiking
Relax or be active! The choice is yours in this pet-friendly family home.
Enjoy cooking in this well-equipped kitchen with a central island, stovetop, and ample counter space.

Relax or be active! The choice is yours in this pet-friendly family home.

10.0 out of 10, Exceptional, (13)
"Home was exactly as listed, very comfortable and convenient for my family’s trip. "
Relax or be active! The choice is yours in this pet-friendly family home.
Falls Reach In The Heart of Copake
Property grounds

Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake
Stylish Pine Plains Home Near Parks & Hiking!
Enjoy cooking in this fully equipped kitchen with a range, oven, microwave, and sink.

Stylish Pine Plains Home Near Parks & Hiking!

9.8 out of 10, Exceptional, (15)
"Place looked great in pictures and turned out to be even better! Will definitely stay there again."
Stylish Pine Plains Home Near Parks & Hiking!
Charming 1870 cape cottage in Litchfield
Relax by the pool surrounded by lush greenery and a serene water feature.

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (52)
"Great location and beautiful setting. Was perfect for the two of us."
Charming 1870 cape cottage in Litchfield
Woodland A-Frame
Spacious living area with a high ceiling, stone accent wall, and kitchen island.

Woodland A-Frame

10.0 out of 10, Exceptional, (1)
"Nice, clean place out in the woods. Enjoyed our stay and had no issues. Host responded quickly and check-in/out was refreshingly simple. Our kid enjoyed the supply of children’s books. "
Woodland A-Frame
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Outdoor dining

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

10.0 out of 10, Exceptional, (5)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel range hood, and large window offering a view of the outdoors.

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

10.0 out of 10, Exceptional, (54)
"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!
YOIN: Whispers of Tranquility, a Zen Retreat
Enjoy meals in this stylish dining area with a long table for four, a pendant light, and a vase with a single flower.

YOIN: Whispers of Tranquility, a Zen Retreat

YOIN: Whispers of Tranquility, a Zen Retreat
Stunning Light-Filled Contemporary Home on 7 Acres
Enjoy a serene view from the large windows, with a seating area and brick-patterned floor.

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
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
Enjoy a formal outdoor dining experience surrounded by lush greenery and tall trees.

Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

2.0 star property
10.0 out of 10, Exceptional, (8)
"We met our kids (who live on the east coast) at Natures Nest and really enjoyed our time here. We cooked 2 big meals and the kitchen had everything we needed…even spices & coffee. And Marco left some apples, sweets and wine for us! He was very responsive and helpful anytime we had questions, and gave us great recommendations. Everything was great!"
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
Indulge in an Elegant Upstate Getaway
Cozy living area with a sofa, chairs, and dining table for four, plus a kitchen with modern appliances and a large island.

Indulge in an Elegant Upstate Getaway

10.0 out of 10, Exceptional, (45)
"We loved the area lots to do great restaurants"
Indulge in an Elegant Upstate Getaway
County Seat Colonial
Relax in a serene bedroom with a large bed, chandelier, and a view through the window.

County Seat Colonial

10.0 out of 10, Exceptional, (11)
"This was just what we needed. Thank you for a beautiful home, adorable town and so much to do! Perfect weekend for my family!"
County Seat Colonial
Cottage at Copake Lake
Situated in a wooded area, this cabin offers a natural and serene environment with a porch and a fire pit for relaxation.

Cottage at Copake Lake

10.0 out of 10, Exceptional, (64)
"We had great relaxing stay. The host was very responsive to any questions i had"
Cottage at Copake Lake
Charming Home with Fireplace and Indoor Pool in Sharon, CT
Relax in a serene garden setting with comfortable wicker seating on a spacious deck.

Charming Home with Fireplace and Indoor Pool in Sharon, CT

10.0 out of 10, Exceptional, (1)
"Our family had a wonderful stay at the beautiful, clean, peaceful Hoyt House. There was plenty of space to gather together as well as spread out. The daffodils were beginning to bloom and there is the sight and sound of a running stream behind the home. We were close to fun things to explore like the Audubon, covered bridge, and Kent waterfalls. Great bakery, restaurants, grocery a short drive away. The heated indoor swimming pool was the biggest hit. We hope to have the opportunity to...
Charming Home with Fireplace and Indoor Pool in Sharon, CT
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

Blackberry River Inn

Blackberry River Inn

10/10 Excellent
"Wonderful breakfast with gluten free options. Beautiful spot/property. Pool was perfect. Clean and comfortable."
Diane 1-night trip
Posted 2 days ago
Blackberry River Inn