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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Lakeville holiday homes

TV, fireplace, books

1. 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, (2 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 £562
includes taxes & fees
17 Aug - 18 Aug
NEW: Chic Modern Barn Style Home in Fun Area
2 bedrooms, free WiFi, 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 £178
includes taxes & fees
30 Aug - 31 Aug
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Coffee/tea maker, fridge, microwave, oven

3. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (37 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is £299
includes taxes & fees
12 Aug - 13 Aug
Home in Great Barrington
Interior

4. 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 £237
includes taxes & fees
19 Aug - 20 Aug
Cozy Riverside Berkshires Retreat
Interior

5. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is £282
includes taxes & fees
30 Aug - 31 Aug
rural, serene + sophisticated space
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 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 £236
includes taxes & fees
1 Sept - 2 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
TV, fireplace, DVD player, books

7. Mtn-View Retreat in Huson Valley: Great for Groups

Mtn-View Retreat in Huson Valley: Great for Groups
Claverack
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful rental - spacious, beautiful views, and gorgeous home!"
United States
Samantha A.
The price is £560
includes taxes & fees
9 Aug - 10 Aug
Mtn-View Retreat in Huson Valley: Great for Groups
Coffee/tea maker, fridge, microwave, oven

8. 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 £1,092
includes taxes & fees
17 Aug - 18 Aug
A Country Lodge Straight Out of the Pages of a Great Novel
Living area

9. Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County

Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Red Hook
10.0 out of 10, Exceptional, (25 reviews)
"It was pet friendly, even for a dog, was comfortable for the entire family and is a great location with easy access to surrounding villages."
United States
Susan T.
The price is £358
includes taxes & fees
23 Aug - 24 Aug
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Dining

10. 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, (8 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 £824
includes taxes & fees
9 Aug - 10 Aug
The George is an elegant restored home in the Hudson Valley
3 bedrooms, iron/ironing board, WiFi, bed sheets

11. 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 £503
includes taxes & fees
8 Sept - 9 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Interior

12. 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 £631
includes taxes & fees
23 Aug - 24 Aug
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
TV, fireplace, printers

13. 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)
"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 £973
includes taxes & fees
19 Aug - 20 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"The breakfast area was small, so no seats available when it was crowded. But that's the only criticism."
Joseph 7-night trip
Posted 2 hours ago
Quality Inn Great Barrington

Find out more about Lakeville

Lakeville Holiday Homes information

Number of reviews
4,619
Accommodation
339 Holiday Homes
Lowest Price
£65
Highest Price
£483