Compare Winery Hotels in Lenox

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Featured Lenox Winery Hotels

Chesapeake Inn of Lenox

Chesapeake Inn of Lenox

3 out of 5
210 West Street Lenox MA
Stay at this golf B&B in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Tanglewood Music Center and Frelinghuysen Morris House ...
Opens in a new windowChesapeake Inn of Lenox
Garden Gables Inn

Garden Gables Inn

4 out of 5
135 Main St Lenox MA
Stay at this hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions The Bookstore and Lenox Library are located nearby.
Opens in a new windowGarden Gables Inn
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
203 Main St Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$333 per night from 21 Dec to 22 Dec
NZ$333
21 Dec - 22 Dec
includes taxes & fees
Stay at this B&B in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the comfy rooms in their reviews. Popular ...
Opens in a new windowThe Cornell Inn, Lenox & The Berkshires
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Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

3.5 out of 5
5 Greenwood Street Lenox MA
Stay at this B&B in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions The Bookstore and Lenox Library are located nearby.
Opens in a new windowWhistler's Inn Bed & Breakfast
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$178 per night from 1 Jan to 2 Jan
NZ$178
1 Jan - 2 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
Opens in a new windowThe Yankee, Trademark Collection by Wyndham
The Dewey

The Dewey

3.5 out of 5
7 Hubbard Street Lenox MA
Stay at this guesthouse in Lenox. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the breakfast in their reviews. Popular attractions ...
Opens in a new windowThe Dewey
Gateways Inn & Restaurant

Gateways Inn & Restaurant

3 out of 5
51 Walker St Lenox MA
The price is NZ$338 per night from 18 Jan to 19 Jan
NZ$338
18 Jan - 19 Jan 2026
includes taxes & fees
Stay at this hotel in Lenox. Enjoy free Wi-Fi, free parking and a business centre. Popular attractions Lenox Library and The Bookstore are located nearby.
Opens in a new windowGateways Inn & Restaurant
Kemble Inn

Kemble Inn

3.5 out of 5
2 Kemble Street Lenox MA
Stay at this boutique inn in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Tanglewood Music Center and Ventfort Hall Mansion ...
Opens in a new windowKemble Inn
Hampton Terrace Inn

Hampton Terrace Inn

4 out of 5
91 Walker Street Lenox MA
The price is NZ$424 per night from 1 Jan to 2 Jan
NZ$424
1 Jan - 2 Jan 2026
includes taxes & fees
Stay at this hotel in Lenox. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Ventfort Hall Mansion and Gilded Age Museum and The Bookstore ...
Opens in a new windowHampton Terrace Inn
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Lenox hotels essential information

Accommodation
1,399 hotels
Lowest Price
NZ$178
Highest Price
NZ$424
Popular hotels
Chesapeake Inn of Lenox, Garden Gables Inn, The Cornell Inn, Lenox & The Berkshires, Whistler's Inn Bed & Breakfast, The Yankee, Trademark Collection by Wyndham, The Dewey, Gateways Inn & Restaurant, Kemble Inn, Hampton Terrace Inn

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