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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, P.O. Box 1920, Lenox, MA
Stay at this 3-star golf B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Frelinghuysen Morris ...
Chesapeake Inn of Lenox
Garden Gables Inn
Garden Gables Inn
4 out of 5
135 Main St, Lenox, MA
Stay at this 4-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and The Bookstore are located ...
Garden Gables Inn
The Cornell Inn, Lenox
The Cornell Inn, Lenox
3 out of 5
203 Main St, Lenox, MA
Stay at this 3-star B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. ...
The Cornell Inn, Lenox
Whistler's Inn Bed & Breakfast
Whistler's Inn Bed & Breakfast
3.5 out of 5
5 Greenwood Street, Lenox, MA
Stay at this 3.5-star B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and The Bookstore are located ...
Whistler'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
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Yankee, Trademark Collection by Wyndham
Gateways Inn & Restaurant
Gateways Inn & Restaurant
3 out of 5
51 Walker St, Lenox, MA
Stay at this 3-star hotel in Lenox. Enjoy free WiFi, free parking, and a business center. Popular attractions Tanglewood Music Center and Lenox Library are located ...
Gateways Inn & Restaurant
Kemble Inn
Kemble Inn
3.5 out of 5
2 Kemble Street, Lenox, MA
Stay at this 3.5-star boutique inn in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Ventfort Hall ...
Kemble Inn
Hampton Terrace Inn
Hampton Terrace Inn
4 out of 5
91 Walker Street, Lenox, MA
Stay at this 4-star hotel in Lenox. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tanglewood Music Center and Ventfort Hall Mansion ...
Hampton Terrace Inn
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
2.5 out of 5
445 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hampton Inn & Suites Berkshires-Lenox
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox
2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Fully refundableReserve now, pay when you stay
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Howard Johnson by Wyndham Lenox
Wagon Wheel Inn
Wagon Wheel Inn
2 out of 5
484 Pittsfield Rd, PO Box 808, Lenox, MA
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Guido's ...
Wagon Wheel Inn
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.

Lenox Winery Hotels

Looking for a glass (more than) half full kind of experience on your last-minute getaway to Lenox? You can’t get more cup runneth over than booking a sip-filled stay at winery hotels. The only thing left to do? Get ready to pop bottles on bubbly good times.

Cheers to Good Deals

When it comes to the best places to stay in Lenox, winery hotels definitely come out on top. And while you may think you’ll have to blow stacks of cash on your perfect place to un-wine-d, you don’t have to dip into your vino budget for an amazing spot to stay. Thanks to Hotwire Hot Rate Lenox winery hotels deals, you can secure a top-shelf hotel for cheap Lenox hotels prices.

Drinking in the Good Times in Lenox

The ultimate in vacay bliss? You, relaxing in your Lenox winery hotel after a fantastic day of wine tasting and vineyard strolling. This doesn’t have to be pinned away on your “one day” bucket list—booking a Hotwire Hot Rate hotel deal can make this primo daydream a reality. And for way less than you expected. The biggest dilemma you’ll have to face on your Lenox getaway is red, white, or rosé?

Frequently Asked Questions About Winery Hotels

How to get last-minute deals on winery hotels in Lenox?

Scoring a fantastic Lenox winery hotel deal is as easy and breezy as a glass of Riesling on a summer’s day when you book a Hotwire Hot Rate hotel deal, even if you wait until the last minute. Because you could save up to 60% off versus booking a listed rate two weeks earlier with Hotwire’s last-minute deals. And with hotels as low as $77, you don’t have to worry about the cost of your stay sipping into your bottle budget. Cheers to the very best deals on Lenox winery hotels.

How many winery hotels are in Lenox?

With 1,308 Lenox winery hotels to choose from, you’re sure to find a spot to please your picky palate. Especially when you can count on finding some of the best places to stay in Lenox ready for the picking with Hotwire Hot Rate deals. Four-star hotels at 2-star prices? That calls for a celebration. Good thing there’s sure to be something sparkling nearby.

How to find cheap winery hotels in Lenox?

Booking cheap winery hotels in Lenox is a simple task. Check out all of the best and bubbly deals available, and then choose which spot best suits your tastes. When you pick a Hotwire Hot Rate hotel deal you won’t know the exact hotel name until after you’ve booked, but know that you’ll soon be toasting to your impeccable money-saving skills and the sweet spot you just scored.

Is it safe to travel to Lenox during the coronavirus (COVID-19) crisis?

With the most recent COVID-19 closures and reopenings, you may be wondering is it safe to travel to Lenox right now. When booking your last-minute getaway to Lenox winery hotels, make sure to check out the latest information on safety measures, closures, and up-to-date guidance on traveling during the coronavirus.