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Compare 297 Vacation Homes in Lakeville with updated reviews, rates, and availability.

Front entrance of the home
Luxury Rhinebeck NY Home on 5 Acres w/ NEW Hot Tub. Great for Families & Groups
10.0 out of 10, Exceptional, (85)
"As we drove up the long driveway to this house we quickly felt it was a home for the next few days we stayed there. The space was inviting, comfortable, clean and the decor was beautiful. Our daughter absolutely loved celebrating her 13th birthday at this beautiful home. It was instant relaxation as the surroundings are beautiful and quiet. Gretchen was a lovely host who was very easy to communicate with and provided such helpful information for us during our stay. A few weeks later and we are...
Luxury Rhinebeck NY Home on 5 Acres w/ NEW Hot Tub. Great for Families & Groups
Front of home
Newly Renovated Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (18)
"The property was perfect for our needs. Instructions for everything was provided fabulous rental. "
Newly Renovated Family House On Highland Lake with Dock
Outdoor dining
Charming 1870 cape cottage in Litchfield
10.0 out of 10, Exceptional, (21)
"The cottage house had a warm, welcoming vibe to it. It was very well maintained. The grounds were beautiful. The home had everything available that you could possibly want. It was very cozy. We had relatives from Italy with us and they absolutely loved it. I would definitely go back and I highly recommend it. Congratulations to the owners, because they have done a wonderful job with it."
Charming 1870 cape cottage in Litchfield
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Exterior
Litchfield County Getaway
10.0 out of 10, Exceptional, (35)
"Very nicely renovated house. Clean and comfortable. Well equipped kitchen. Large comfy living and dining room. Very responsive hosts. Only suggestion would be to provide a few more hooks in the bathrooms for guests to hang personal things (night clothes, used towels, etc.). I would highly recommended this place."
Litchfield County Getaway
Exterior
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
10.0 out of 10, Exceptional, (10)
"We had a lovely weekend at this updated farm house. The house is a great combination of old comfortable farm house and updated and clean kitchens and bathrooms. We loved having Artie, the kitty, as our welcoming party."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Dining
Sweet Cozy Victorian in Housatonic. Close to everything.
The price is SAR 563
SAR 976 total
includes taxes & fees
29 Jum. I - 30 Jum. I
Sweet Cozy Victorian in Housatonic. Close to everything.
Renovated 9-BR 1800s Inn 8-Min to Catamount
Renovated 9-BR 1800s Inn 8-Min to Catamount
Kitchen and dining room
Hudson Valley and The Berkshires getaway
10.0 out of 10, Exceptional, (1)
"Overnight golf trip with cousins and father. Perfect accommodations not far from the copake country club. Great time"
Hudson Valley and The Berkshires getaway
Room
Private Annex/Former Artist Studio
10.0 out of 10, Exceptional, (38)
"This charming 2-bedroom New Preston apartment was the perfect escape! Cozy rooms welcomed us with peace and comfort, melting away city stress. Host Melanie's warm smile and delicious homemade cookies added a personal touch that made our stay truly heartwarming. Reconnecting with nature was easy - breathtaking scenery, quiet streets, and a nearby lake offered peaceful beauty. This wasn't just a place to stay, it was an experience we'll treasure. Highly recommend! ⭐⭐⭐⭐⭐ P.S. too bad I forgot...
Private Annex/Former Artist Studio
Breathtaking Mountain Views.
Mountain View Getaway
10.0 out of 10, Exceptional, (36)
"Couldn’t ask for better hosts! The house is impeccable and the views are amazing!"
Mountain View Getaway
Peaceful, Post and Beam Loft, Sleeps 9
10.0 out of 10, Exceptional, (8)
"beautifully stay for couples."
Peaceful, Post and Beam Loft, Sleeps 9
Sunrise lights up the front of the house. Moon sets over the mountain.
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (79)
"There were 6 adults and 2 infants in our party, we were in town for our 25 year high school reunion. The house was incredible and the host went above and beyond to make sure we were well taken care of. This place is a hidden gem and deserves all of the praise."
Antique Farmhouse Totally Restored
Great Barrington Get Away
9.6 out of 10, Exceptional, (17)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
Great Barrington Get Away
Amazing Entertainment Space
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
10.0 out of 10, Exceptional, (126)
"Great time, beautiful property, host very responsive and helpful. Awesome sound system bring your CDs."
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
Living area
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, (7)
"We had a great stay while skiing for 2 days at nearby Catamount ski resort. The kitchen and house were fully stocked with all essentials. Netflix access enabled us to enjoy a family movie after a long day of skiing. Cozy house and quiet area.......nice to wake up to hear birds chirping!!"
The price is SAR 596
SAR 1,228 total
includes taxes & fees
27 Jum. I - 28 Jum. I
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior
Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.
10.0 out of 10, Exceptional, (2)
"We absolutely loved the place! Tons of space, all new appliances, fire pit and the gorgeous master bathroom were all highlights of our stay. Super convenient location within a few minutes of the Stop and Shop as well as other stores. Andrea was very friendly and attentive. She was there to quickly answer any questions we had and made sure we had everything we needed. Highly recommend!"
Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.
Aerial view
Remodeled Lakefront retreat with beautiful dock, lakeside firepit and more!!!
Remodeled Lakefront retreat with beautiful dock, lakeside firepit and more!!!
Sheffield Vacation Rental | 3BR | 2BA | 2,262 Sq Ft | 2 Steps to Enter
Waterview Home in the Berkshires: Near Hiking
9.2 out of 10, Wonderful, (14)
"Lovely house and kind owner. We had a great time. The view is amazing."
Waterview Home in the Berkshires: Near Hiking
Hillsdale Vacation Rental | 6BR | 2.5BA | 3,600 Sq Ft | Stairs Required
Waterfalls and Trails at 'The Mills At Green Hole'
10.0 out of 10, Exceptional, (10)
"Corporate retreat for annual planning"
Waterfalls and Trails at 'The Mills At Green Hole'
Quiet and peaceful gray cape cod located on rural lake setting!
Indulge in an Elegant Upstate Getaway
10.0 out of 10, Exceptional, (41)
"Love this property, so quiet and beaviews. Tastefully decorated. Felt like home."
Indulge in an Elegant Upstate Getaway
Don't see what you're looking for?
See all available properties in Lakeville
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.

Other property types in Lakeville

Welcome to The Freeman Berkshires
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Front of home
Newly Renovated Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (18)
"The property was perfect for our needs. Instructions for everything was provided fabulous rental. "
Newly Renovated 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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