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Check prices for these dates

Next weekend
26 Sept - 28 Sept
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3 Oct - 5 Oct
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17 Oct - 19 Oct
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14 Nov - 16 Nov

Featured Cottages in Lakeville and around

Our top choices for Lakeville cottages

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 €349
includes taxes & fees
23 Sept - 24 Sept
The Blue Elm - A Historic Berkshire Cottage
Pet-friendly Cottage at Historic Millbrook Farm Estate
Exterior

Pet-friendly Cottage at Historic Millbrook Farm Estate

9.2 out of 10, Wonderful, (14)
"Great location, neat and tidy. Hosts are great, too."
Pet-friendly Cottage at Historic Millbrook Farm Estate
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
Two Bedroom Cottage Close To Town
Exterior

Two Bedroom Cottage Close To Town

9.2 out of 10, Wonderful, (24)
"The house had everything we needed. The full kitchen served us well, the beds were comfortable, and the showers were great!"
Two Bedroom Cottage Close To Town
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Property grounds

The Cottage at Highland Lake, year-round, waterfront with a boat dock

10.0 out of 10, Exceptional, (6)
"Really enjoyed this cute little cottage right on the lake. Brought our 3 year old to visit family. Nice bedrooms. Gorgeous deck. Really good communication from the owner as far as directions and such. Would go back for sure. "
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Idillic summer getaway in Litchfield Hills, CT.
Exterior

Idillic summer getaway in Litchfield Hills, CT.

10.0 out of 10, Exceptional, (13)
"Great spot close to Limerock Raceway - private, cute, and a perfect spot to stay! The owners are so nice and accommodating - I couldn’t say nicer things about this place and will be back!"
Idillic summer getaway in Litchfield Hills, CT.
Lakefront Tranquility/Fishermans Delight
Property grounds

Lakefront Tranquility/Fishermans Delight

9.8 out of 10, Exceptional, (20)
"Great cabin very relaxing"
Lakefront Tranquility/Fishermans Delight
Light-filled cottage
Exterior

Light-filled cottage

10.0 out of 10, Exceptional, (1)
"Beautiful, well-designed home deserves a 10 out of 10 for aesthetics. Very glad Jing (the host) and her family are sharing this jewel of a home with the rest of us. Jing was a quick, kind and cordial communicator. The house location was quiet and tranquil. Nearby lake was within walking distance and delightful."
Light-filled cottage
Creekside Cottage The Fitz House Red Hook NY
Exterior

Creekside Cottage The Fitz House Red Hook NY

10.0 out of 10, Exceptional, (5)
"We had a wonderful stay. Communication with host was excellent. Highly recommend the location for a couple."
Creekside Cottage The Fitz House Red Hook NY
Stylish Pine Plains Home Near Parks & Hiking!
House (1 Bedroom) | Interior

Stylish Pine Plains Home Near Parks & Hiking!

3.0 star property
10.0 out of 10, Exceptional, (1)
Stylish Pine Plains Home Near Parks & Hiking!
Charming 3bdr Magnolia cottage with heated saltwater pool, AC and WiFi in Amenia
Exterior

Charming 3bdr Magnolia cottage with heated saltwater pool, AC and WiFi in Amenia

10.0 out of 10, Exceptional, (4)
"This was the perfect size cottage for 5 of us, with two rooms with queen size beds and one small room with a twin. The setting was very pretty, and the salt water heated pool was a good size and my grandchildren enjoyed swimming in it. We were within walking distance of the small town, and I would recommend staying there."
Charming 3bdr Magnolia cottage with heated saltwater pool, AC and WiFi in Amenia
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
Outdoor dining

Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake

10.0 out of 10, Exceptional, (7)
"Very cozy, very nice views, tranquil, serene. "
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
Cozy 2-bedroom Cottage with Access to Bantam Lake
Property grounds

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (18)
"Even with horrible weather, we had a wonderful stay!"
Cozy 2-bedroom Cottage with Access to Bantam Lake
Reset and Relax in Luxury Cottage
Property grounds

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (42)
"Amazing floors, bathroom showers (wow!), and an awesome kitchen."
Reset and Relax in Luxury Cottage
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Exterior

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.4 out of 10, Exceptional, (15)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Charming & Great Location!
Exterior

Charming & Great Location!

10.0 out of 10, Exceptional, (1)
"The property is amazing. The house is beautiful and very inviting and comfortable. It was easy to locate. Even though the property was older with loads of charm it was updated with many modern conveniences. The owner stayed in contact to make sure we had everything we needed. We would stay again. "
Charming & Great Location!
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!
House (4 Bedrooms) | Interior

Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

3.0 star property
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!
Perfect Vacation Get Away - Historical New Marlborough
Exterior

Perfect Vacation Get Away - Historical New Marlborough

9.2 out of 10, Wonderful, (57)
"Had a great time. If you love to get away from the cities and relax this is it. Bring what you need as theres no stores close."
Perfect Vacation Get Away - Historical New Marlborough
Our Cottage - Small in size, Big in character, On beautiful Highland Lake
Exterior

Our Cottage - Small in size, Big in character, On beautiful Highland Lake

10.0 out of 10, Exceptional, (45)
"Excellent place with modern decor inside and beautiful view of lake from very nice deck. Will definitely stay again! "
Our Cottage - Small in size, Big in character, On beautiful Highland Lake
Peaceful Goshen Cottage w/ Screened Porch & Views!
Cottage (3 Bedrooms) | Interior

Peaceful Goshen Cottage w/ Screened Porch & Views!

3.0 star property
Peaceful Goshen Cottage w/ Screened Porch & Views!
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 Lakeville Hotel Reviews

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent
"Otto couldn’t have been more helpful at checkin. Great recommendations for hotels and places to go."
Mary 1-night trip
Posted 3 days ago
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Find out more about Lakeville

Find out more about Lakeville

Lakeville Cottages information

Number of reviews
325
Accommodation
84 Cottages
Lowest Price
€349
Highest Price
€349

Frequently asked questions

Why book your cottage in Lakeville with Expedia?
Booking a cottage in Lakeville is as easy as deciding on your travel dates and choosing your ideal place for outdoor fun and relaxation. From ritzy retreats to low-cost stays and cottages that offer perks like a pool, Expedia has something for all tastes and styles. As for epic deals? We've got your back!
How can I find cheap cottages in Lakeville?
Expedia is here to help you look for cheap cottages in Lakeville. To find a terrific stay in a couple of clicks, try out our convenient filter tool to refine your search results by budget, star rating and amenities.
What is there to do in Lakeville near my cottage?
The best travel accessory is a well-thought-out travel plan. Lime Rock Park is a wonderful place to start your exploration of Lakeville.

Explore a world of travel with Expedia

Explore a world of travel with Expedia