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Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Lakeville vacation homes

Property grounds

1. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 907
AED 1,908 total
includes taxes & fees
22 Sep - 23 Sep
Cheerful 3-bedroom cottage with woodstove
2 bedrooms, WiFi (free), bed sheets

2. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is AED 456
AED 828 total
includes taxes & fees
13 Sep - 14 Sep
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Miscellaneous

3. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is AED 1,653
AED 2,547 total
includes taxes & fees
9 Sep - 10 Sep
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
TV, fireplace, books

4. 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 990
AED 2,878 total
includes taxes & fees
22 Sep - 23 Sep
NEW: Chic Modern Barn Style Home in Fun Area
Coffee/tea maker, fridge, microwave, oven

5. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is AED 876
AED 1,352 total
includes taxes & fees
7 Sep - 8 Sep
Home in Great Barrington
Interior

6. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AED 744
AED 1,163 total
includes taxes & fees
8 Sep - 9 Sep
Cozy Riverside Berkshires Retreat
Interior

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 1,502 total
includes taxes & fees
8 Sep - 9 Sep
rural, serene + sophisticated space
Exterior

8. Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam
Hillsdale
8.4 out of 10, Very Good, (5 reviews)
"Overall a very pleasant stay. It is a cool old house with all its charm and quirks. Very spacious, comfortable. Decent kitchen. Location very accessible for mountains and tooling around. Just right for a getaway"
United States
Annetta D.
The price is AED 683
AED 1,963 total
includes taxes & fees
13 Sep - 14 Sep
Perfect House In Hillsdale, Brings Friends & Fam
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is AED 643
AED 1,173 total
includes taxes & fees
3 Sep - 4 Sep
Sweet Cozy Victorian in Housatonic. Close to everything.
Smart TV, books

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

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is AED 1,483
AED 2,484 total
includes taxes & fees
2 Sep - 3 Sep
Fantastic 2-bedroom house with AC in quaint Hillsdale.
Coffee/tea maker, fridge, microwave, oven

11. 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)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is AED 3,269
AED 5,393 total
includes taxes & fees
8 Sep - 9 Sep
A Country Lodge Straight Out of the Pages of a Great Novel
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 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 1,165
AED 2,036 total
includes taxes & fees
14 Sep - 15 Sep
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Dining

13. The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.6 out of 10, Exceptional, (9 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 price is AED 2,645
AED 4,109 total
includes taxes & fees
2 Sep - 3 Sep
The George is an elegant restored home in the Hudson Valley
Interior

14. 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, (6 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 3,083 total
includes taxes & fees
6 Sep - 7 Sep
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
TV, fireplace, printers

15. 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, (7 reviews)
"Beautiful house with great amenities in a convenient location. We loved the open concept that provided a great space for cooking, hanging out and playing games together while enjoying a beautiful view. The gameroom was so much fun, and we’d love to visit again when the sauna is finished. Our family of 6 and family dog loved it!"
United States
Rebecca K.
The price is AED 2,089
AED 4,869 total
includes taxes & fees
2 Sep - 3 Sep
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Exterior

16. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is AED 9,917
AED 12,874 total
includes taxes & fees
1 Oct - 2 Oct
Las Flores Villa
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

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

10/10 Excellent
"This was such a charming B&B. Clean rooms and bathrooms. The property was gorgeous!"
Amanda 2-night trip
Posted 1 hour ago
Locust Tree Bed and Breakfast LLC

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