Book Guest Houses in Lakeville, CT

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Top Guest Houses in Lakeville

9 Academy

9 Academy St Salisbury CT

$469 nightly

$540 total

Dec 17 - Dec 18

Total with taxes and fees

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, express check-in, and express check-out are also on offer.

Parking included

Free WiFi

Hudson valley and The Berkshires Cottage

Hillsdale NY

$294 nightly

$298 total

Dec 15 - Dec 16

Total with taxes and fees

This guesthouse includes a garden and laundry facilities.

Pet friendly

Free WiFi

Renovated Private Guest House by Evergreen Home

Great Barrington MA

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This guesthouse features a garden, laundry facilities, and barbecue grills.

Pet friendly

Free WiFi

1805 House Bed and Breakfast

775 Snydertown Road Craryville NY

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This guesthouse features free self parking and a terrace. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.

Breakfast included

Parking included

Vanderbilt Lakeside

161 Main St Philmont NY

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This guesthouse features free WiFi in public areas, wedding services, and free self parking. Enjoy the free continental breakfast each morning. A terrace, a garden, and a communal living room are also on offer.

Breakfast included

Parking included

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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.

Top hotels in Lakeville

Prospect Berkshires

50 Prospect Lake Rd Egremont MA

$272 nightly

$304 total

Jan 13 - Jan 14, 2026

Total with taxes and fees

9.4/10 Exceptional! (15 reviews)

Lakeville Guest Houses essential information

Accommodation	5 Guest Houses
Lowest Price	$85
Highest Price	$540
Popular accommodation	9 Academy , Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, 1805 House Bed and Breakfast , Vanderbilt Lakeside