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Our top choices for Lakeville vacation homes

1. 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 AED 651
AED 1,503 total
includes taxes & fees
18 Nov - 19 Nov
Cheerful 3-bedroom cottage with woodstove

2. 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, (6 reviews)
The price is AED 364
AED 673 total
includes taxes & fees
22 Nov - 23 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester

3. NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
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 AED 665
AED 2,593 total
includes taxes & fees
15 Dec - 16 Dec
NEW: Chic Modern Barn Style Home in Fun Area

4. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is AED 1,653
AED 2,402 total
includes taxes & fees
16 Nov - 17 Nov
Chic Lakeside Oasis|Near Rhinebeck & Millbrook

5. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is AED 735
AED 1,112 total
includes taxes & fees
13 Dec - 14 Dec
Home in Great Barrington

6. 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 AED 2,877
AED 4,663 total
includes taxes & fees
17 Nov - 18 Nov
A Country Lodge Straight Out of the Pages of a Great Novel

7. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is AED 1,172
AED 1,407 total
includes taxes & fees
16 Dec - 17 Dec
rural, serene + sophisticated space

8. 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, (15 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

9. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is AED 1,396
AED 2,258 total
includes taxes & fees
16 Nov - 17 Nov
Fantastic 2-bedroom house with AC in quaint Hillsdale.

10. 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 AED 1,469
AED 2,796 total
includes taxes & fees
23 Nov - 24 Nov
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

11. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (10 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is AED 2,033
AED 4,367 total
includes taxes & fees
20 Nov - 21 Nov
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

12. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is AED 1,502
AED 2,490 total
includes taxes & fees
16 Nov - 17 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.

13. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is AED 3,289
AED 5,252 total
includes taxes & fees
16 Nov - 17 Nov
Las Flores Villa

14. A Cozy Berkshire Escape l Close to the Slopes

A Cozy Berkshire Escape l Close to the Slopes
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is AED 744
AED 1,102 total
includes taxes & fees
16 Nov - 17 Nov
A Cozy Berkshire Escape l Close to the Slopes

15. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is AED 646
AED 1,120 total
includes taxes & fees
16 Nov - 17 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.

16. Lockwood Manor: Autumn Escape on Six Private Acres with Heated Pool

Lockwood Manor: Autumn Escape on Six Private Acres with Heated Pool
Hillsdale
Lockwood Manor: Autumn Escape on Six Private Acres with Heated Pool
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

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