
Search Vacation Homes in Lakeville
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Lakeville vacation homes

1. Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstoveSheffield
10.0 out of 10, Exceptional, (46 reviews)
The price is AED 651
AED 1,503 total
includes taxes & fees
18 Nov - 19 Nov

2. Peaceful and cozy 1 bed 1 bath in quaint Winchester
Peaceful and cozy 1 bed 1 bath in quaint WinchesterWinchester
10.0 out of 10, Exceptional, (6 reviews)
The price is AED 364
AED 673 total
includes taxes & fees
22 Nov - 23 Nov

3. NEW: Chic Modern Barn Style Home in Fun Area
NEW: Chic Modern Barn Style Home in Fun AreaPine Plains
10.0 out of 10, Exceptional, (3 reviews)
The price is AED 665
AED 2,593 total
includes taxes & fees
15 Dec - 16 Dec

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

5. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (42 reviews)
The price is AED 735
AED 1,112 total
includes taxes & fees
13 Dec - 14 Dec

6. A Country Lodge Straight Out of the Pages of a Great Novel
A Country Lodge Straight Out of the Pages of a Great NovelPine Plains
10.0 out of 10, Exceptional, (15 reviews)
The price is AED 2,877
AED 4,663 total
includes taxes & fees
17 Nov - 18 Nov

7. rural, serene + sophisticated space
rural, serene + sophisticated spaceRed Hook
10.0 out of 10, Exceptional, (9 reviews)
The price is AED 1,172
AED 1,407 total
includes taxes & fees
16 Dec - 17 Dec

8. The George is an elegant restored home in the Hudson Valley
The George is an elegant restored home in the Hudson ValleyStanfordville
9.8 out of 10, Exceptional, (15 reviews)

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

10. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Steps to the Delightful Village of Millbrook ☆ Fun Family GetawayMillbrook
10.0 out of 10, Exceptional, (8 reviews)
The price is AED 1,469
AED 2,796 total
includes taxes & fees
23 Nov - 24 Nov

11. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness roomGreat Barrington
10.0 out of 10, Exceptional, (10 reviews)
The price is AED 2,033
AED 4,367 total
includes taxes & fees
20 Nov - 21 Nov

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 price is AED 1,502
AED 2,490 total
includes taxes & fees
16 Nov - 17 Nov

13. Las Flores Villa
Las Flores VillaNew 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

14. A Cozy Berkshire Escape l Close to the Slopes
A Cozy Berkshire Escape l Close to the SlopesGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
The price is AED 744
AED 1,102 total
includes taxes & fees
16 Nov - 17 Nov

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)
The price is AED 646
AED 1,120 total
includes taxes & fees
16 Nov - 17 Nov

16. Lockwood Manor: Autumn Escape on Six Private Acres with Heated Pool
Lockwood Manor: Autumn Escape on Six Private Acres with Heated PoolHillsdale
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.
Find vacation rentals that suit your style
Apartments
Private vacation homes
Save an average of 15% on thousands of hotels when you're signed in
Top Lakeville Hotel Reviews

Quality Inn Great Barrington
8/10 Good
Explore a world of travel with Expedia
- Winery Hotels in Litchfield
- Farmstay in Milton Center Historic District
- Hotels near Hotchkiss-Fyler House Museum
- Condo Rentals in Norfolk
- Condo Rentals in Sharon
- Lodges in Torrington
- Villas in South Kent
- Chalets in Colebrook
- Vacation Homes in Winsted
- Wyndham Hotels in Sharon
- Wyndham Hotels in Lakeville
- Hilton Hotels in Milton Center Historic District
- Cabin Rentals in Kent
- 2 Star Hotels in West Cornwall
- La Quinta Inn & Suites Hotels in New Preston
- Cabin Rentals in Lime Rock
- Hilton Hotels in New Preston
- Condo Rentals in South Kent
- Apartments in Lime Rock
- Rv Parks in Lakeville
- Beach Hotels in Kent
- Condo Rentals in New Preston
- Relais & Chateaux Hotels in Milton Center Historic District
- Hotels near Winchester Historical Society
- Condo Rentals in Salisbury
- Business Hotels in Colebrook
- 5 Star Hotels in Lakeville
- Marriott Hotels & Resorts in Goshen
- Relais & Chateaux Hotels in Cornwall Bridge
- Cabin Rentals in Torrington
- Hilton Hotels in Winsted
- 5 Star Hotels in Salisbury
- 3 Star Hotels in Salisbury
- Hilton Hotels in Goshen
- Wyndham Hotels in Norfolk
- Independent Hotels in Litchfield Historic District
- Rv Parks in Salisbury
- 4 Star Hotels in Cornwall Bridge
- Rv Parks in West Cornwall
- Hotels with a Pool in Cornwall Bridge
- 4 Star Hotels in Falls Village
- Relais & Chateaux Hotels in Kent
- 4 Star Hotels in Winsted
- 5 Star Hotels in Kent
- 4 Star Hotels in Goshen
- Hotels with WiFi in Salisbury
- Wyndham Hotels in Colebrook
- 4 Star Hotels in Kent
- 3 Star Hotels in Colebrook
- 5 Star Hotels in West Cornwall
- 2 Star Hotels in New Preston
- 5 Star Hotels in Litchfield
- Wyndham Hotels in Goshen
- B&B in East Canaan
- Inns in Kent
- Villas in Goshen
- 5 Star Hotels in Sharon
- Wyndham Hotels in Milton Center Historic District
- Chalets in Canann Village Historic District
- Cottages in New Preston
- Adventure Hotels in Colebrook
- B&B in Lime Rock
- Wyndham Hotels in Salisbury
- 3 Star Hotels in Milton Center Historic District
- B&B in Torrington
- Rv Parks in Warren
- Guest Houses in Kent
- Inns in West Cornwall
- 3 Star Hotels in Weatogue
- Wyndham Hotels in Winsted
- Historic Hotels in Sharon
- Wyndham Hotels in Warren
- 2 Star Hotels in Sharon
- B&B in Winsted
- Cabin Rentals in Goshen
- Wyndham Hotels in Lime Rock
- Marriott Hotels & Resorts in Norfolk
- 3 Star Hotels in Bantam
- Apartments in Cornwall Bridge
- Relais & Chateaux Hotels in Goshen
- Marriott Hotels & Resorts in Colebrook
- Flights from Salisbury
- Flights to Cornwall Bridge
- Flights from Lakeville
- Flights from Falls Village
- Flights from South Kent
- Flights from Goshen
- Flights from Colebrook
- Flights from Norfolk
- Flights from East Canaan
- Flights from Bantam
- Flights from Milton Center Historic District
- Flights from West Cornwall
- Flights from New Preston
- Flights from Weatogue

















































