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Winery Hotels in Western Massachusetts

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Featured Western Massachusetts Winery Hotels

The Old Inn On The Green
The Old Inn On The Green
4 out of 5
134 Hartsville-New Marlborough Rd, New Marlborough, Great Barrington, MA
Stay at this 4-star inn in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Questing and New Marlborough Town Library ...
The Old Inn On The Green
Shaker Mill Inn
Shaker Mill Inn
2.5 out of 5
2 Oak Street, West Stockbridge, MA
Stay at this B&B in West Stockbridge. Enjoy free breakfast, free parking, and daily housekeeping. Popular attractions Tanglewood Music Center and Ebenezer II ...
Shaker Mill Inn
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Best Western Plus Berkshire Hills Inn & Suites
Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge
2 out of 5
42 Stockbridge Rd, West Stockbridge, MA
Fully refundableReserve now, pay when you stay
Stay at this motel in West Stockbridge. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
Pleasant Valley Motel West Stockbridge
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
Monument Mountain Motel
Monument Mountain Motel
2.5 out of 5
247 Stockbridge Rd, Great Barrington, MA
Fully refundableReserve now, pay when you stay
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Monument Mountain Motel
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
Fully refundableReserve now, pay when you stay
Book a stay at this family-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Quality Inn
Quality Inn
2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Quality Inn
Lantern House Motel
Lantern House Motel
2.5 out of 5
256 Stockbridge Road, Great Barrington, MA
Stay at this motel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Housatonic River and Lake Mansfield Park are located ...
Lantern House Motel
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
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.

Western Massachusetts Winery Hotels

Looking for a glass (more than) half full kind of experience on your last-minute getaway to Western Massachusetts? 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 Western Massachusetts, 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 Western Massachusetts winery hotels deals, you can secure a top-shelf hotel for cheap Western Massachusetts hotels prices.

Drinking in the Good Times in Western Massachusetts

The ultimate in vacay bliss? You, relaxing in your Western Massachusetts 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 Western Massachusetts getaway is red, white, or rosé?

Frequently Asked Questions About Winery Hotels

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

Scoring a fantastic Western Massachusetts 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 $70, you don’t have to worry about the cost of your stay sipping into your bottle budget. Cheers to the very best deals on Western Massachusetts winery hotels.

How many winery hotels are in Western Massachusetts?

With 1,337 Western Massachusetts 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 Western Massachusetts 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 Western Massachusetts?

Booking cheap winery hotels in Western Massachusetts 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 Western Massachusetts 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 Western Massachusetts right now. When booking your last-minute getaway to Western Massachusetts winery hotels, make sure to check out the latest information on safety measures, closures, and up-to-date guidance on traveling during the coronavirus.