Winery Hotels in Western Massachusetts, MA
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Featured Western Massachusetts Winery Hotels

The Old Inn On The Green
134 Hartsville-New Marlborough Rd Great Barrington MA
$319 nightly
The price is $350 total per night
$350 total
Nov 5 - Nov 6
Total with taxes and fees
The Old Inn On The Green features free WiFi in public areas, a seasonal outdoor pool, and a meeting room. If you drive, take advantage of free parking. Additional amenities include a terrace and a garden.
Pool
Breakfast included

Shaker Mill Inn
2 Oak Street West Stockbridge MA
$145 nightly
The price is $159 total per night
$159 total
Nov 5 - Nov 6
Total with taxes and fees
Shaker Mill Inn features free WiFi in public areas and a library. There's free parking if you drive.
Parking included
Free WiFi

Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $104 total per night
$104 total
Dec 1 - Dec 2
Total with taxes and fees
Guests of Best Western Plus Berkshire Hills Inn & Suites enjoy a gym, free WiFi in public areas, and conference space. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to assist with securing valuables, luggage storage, and tours or tickets. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a 24-hour business center, coffee/tea in a common area, and a computer station.
Breakfast included
Pet friendly

Pleasant Valley Motel West Stockbridge
42 Stockbridge Rd West Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $78 total per night
$78 total
Nov 5 - Nov 6
Total with taxes and fees
Guests of Pleasant Valley Motel West Stockbridge enjoy features like free WiFi in public areas. If you drive, put free parking to good use. Staff members can help with accommodation requests, and provide front-desk service during limited hours.
Parking included
Free WiFi

Chesapeake Inn of Lenox
210 West Street Lenox MA
At Chesapeake Inn of Lenox, guests have access to an outdoor pool, free WiFi in public areas, and an outdoor tennis court. You can take advantage of free parking, along with a free area shuttle. Front-desk staff can answer questions 24/7, and assist with dry cleaning/laundry, luggage storage, and tours or tickets. Other amenities at this adults-only bed & breakfast include a business center, a meeting room, and free newspapers.
Pool
Breakfast included

Monument Mountain Motel
247 Stockbridge Rd Great Barrington MA
Free Cancellation
Reserve now, pay when you stay
$67 nightly
The price is $74 total per night
$74 total
Nov 5 - Nov 6
Total with taxes and fees
Monument Mountain Motel features free WiFi in public areas and barbecue grills. If you decide to drive, there's free parking. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. This smoke-free motel also has a picnic area.
Parking included
Free WiFi

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
249 Stockbridge Rd Great Barrington MA
Free Cancellation
Reserve now, pay when you stay
$161 nightly
The price is $179 total per night
$179 total
Nov 9 - Nov 10
Total with taxes and fees
Guests staying at Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. If you drive, put free parking to good use. The front desk is staffed 24 hours a day to help with dry cleaning/laundry and securing valuables. Additional amenities include a business center, coffee/tea in a common area, and a meeting room.
Pool
Breakfast included

Quality Inn Great Barrington
372 Main Street Great Barrington MA
Free Cancellation
$76 nightly
The price is $85 total per night
$85 total
Nov 25 - Nov 26
Total with taxes and fees
Guests of Quality Inn Great Barrington enjoy a gym, free WiFi in public areas, and coffee in a common area. You can put free parking to good use if you drive. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include a microwave in a common area, free newspapers, and a water dispenser.
Breakfast included
Parking included

Lantern House Motel
256 Stockbridge Road Great Barrington MA
Guests of Lantern House Motel enjoy free WiFi in public areas, a seasonal outdoor pool, and a picnic area. If you decide to drive, there's free parking. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. This motel also has a garden.
Pool
Breakfast included

The Cornell Inn, Lenox & The Berkshires
203 Main St Lenox MA
Free Cancellation
Reserve now, pay when you stay
$178 nightly
The price is $198 total per night
$198 total
Nov 8 - Nov 9
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires features free WiFi in public areas, coffee in a common area, and microwave in a common area. If you drive, put free parking to good use. The 24-hour front desk has staff standing by to help with luggage storage and concierge services. Additional amenities include a refrigerator in a common area, a computer station, and a library.
Breakfast included
Parking included

Whistler's Inn Bed & Breakfast
5 Greenwood Street Lenox MA
$126 nightly
The price is $141 total per night
$141 total
Nov 6 - Nov 7
Total with taxes and fees
Whistler's Inn Bed & Breakfast features free WiFi in public areas, coffee in a common area, and a meeting room. Free parking is included with your stay. The front desk has multilingual staff that can help with luggage storage, and offer advice about sights and eateries nearby. Additional amenities include a library, a terrace, and a TV in a common area.
Breakfast included
Pet friendly

The Yankee Inn
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $120 total per night
$120 total
Nov 5 - Nov 6
Total with taxes and fees
The Yankee Inn features an indoor pool, an outdoor pool, and a 24-hour gym. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Additional amenities include free WiFi in public areas, a hot tub, and a seasonal outdoor pool.
Pool
Hot Tub

The Dewey
7 Hubbard Street Lenox MA
At The Dewey, guests have access to free WiFi in public areas, a meeting room, and a library. If you plan to drive, free parking is available. Staff members can help with accommodation requests, and provide concierge services. Additional amenities include express check-out, free newspapers, and a terrace.
Parking included
Free WiFi

Gateways Inn & Restaurant
51 Walker St Lenox MA
$244 nightly
The price is $272 total per night
$272 total
Nov 8 - Nov 9
Total with taxes and fees
Gateways Inn & Restaurant features free WiFi in public areas, conference space, and a business center. If you drive, put free parking to good use. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. Additional amenities include a terrace, wedding services, and a TV in a common area.
Parking included
Free WiFi
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See all available properties in Western Massachusetts
View all propertiesLowest 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 hotels essential information
Accommodation | 1,509 hotels |
|---|---|
Lowest Price | $74 |
Highest Price | $350 |
Popular hotels | The Old Inn On The Green, Shaker Mill Inn, Best Western Plus Berkshire Hills Inn & Suites, Pleasant Valley Motel West Stockbridge, Chesapeake Inn of Lenox, Monument Mountain Motel, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, Quality Inn Great Barrington, Lantern House Motel, The Cornell Inn, Lenox & The Berkshires, Whistler's Inn Bed & Breakfast, The Yankee Inn, The Dewey, Gateways Inn & Restaurant |
Recent Winery Hotels Reviews

MGM Springfield
5/5 Excellent
"Not really a gambler, but the casino activity on the main floor brought a little excitement to the lobby which was nice."
A verified traveler stayed at MGM Springfield
Posted 1 day ago
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