Wedding Venue Hotels in The Berkshires, MA
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Featured The Berkshires Hotels with a Wedding Venue

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

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $99 total per night
$99 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
Guests of Holiday Inn & Suites Pittsfield-Berkshires by IHG have access to an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The 24-hour front desk has multilingual staff ready to assist with securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include a conference center, a 24-hour business center, and a computer station.
Pool
Pet friendly

Eastgate Inn B&B
207 West Street Lenox MA
Guests staying at Eastgate Inn B&B enjoy free WiFi in public areas, a library, and a TV in a common area. You can take advantage of free parking, along with an area shuttle. Additional amenities include a garden, wedding services, and barbecue grills.
Breakfast included
Parking included

Gateways Inn & Restaurant
51 Walker St Lenox MA
$167 nightly
The price is $186 total per night
$186 total
Jan 5 - Jan 6, 2026
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 library, a terrace, and wedding services.
Parking included
Free WiFi

Harbour House Inn
725 North State Road Cheshire MA
$194 nightly
The price is $206 total per night
$206 total
Jan 19 - Jan 20, 2026
Total with taxes and fees
At Harbour House Inn, guests have access to free WiFi in public areas, coffee in a common area, and a library. A stay here includes free parking. Additional amenities include express check-in, express check-out, and a communal living room.
Breakfast included
Parking included

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
$414 nightly
The price is $462 total per night
$462 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Guests of The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood enjoy access to free WiFi in public areas, conference space, and a seasonal outdoor pool. Free parking is included with your stay. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. Other amenities at this luxury bed & breakfast include coffee/tea in a common area, a computer station, and a library.
Pool
Breakfast included

1896 House Country Inn & Motels
910 Cold Spring Road Williamstown MA
$99 nightly
The price is $111 total per night
$111 total
Dec 30 - Dec 31
Total with taxes and fees
1896 House Country Inn & Motels features free WiFi in public areas, conference space, and a business center. Free parking is included with your stay. Staff members are on hand to provide tour or ticket assistance and luggage storage. Additional amenities include a computer station, a terrace, and wedding services.
Pet friendly
Parking included

The Orchards Hotel
222 Adams Rd Williamstown MA
Guests of The Orchards Hotel enjoy a gym, free WiFi in public areas, and meeting rooms. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help with securing valuables, dry cleaning/laundry, and concierge services. Additional amenities include conference space, a business center, and a seasonal outdoor pool.
Pool
Breakfast included

The Red Lion Inn
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
$177 nightly
The price is $198 total per night
$198 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
Guests of The Red Lion Inn have access to an outdoor pool, a gym, and free WiFi in public areas. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, luggage storage, and dry cleaning/laundry. Other amenities at this historic hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa

Whistler's Inn Bed & Breakfast
5 Greenwood Street Lenox MA
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

Travelodge by Wyndham Great Barrington Berkshires
400 Stockbridge Rd Great Barrington MA
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $84 total per night
$84 total
Dec 28 - Dec 29
Total with taxes and fees
Guests staying at Travelodge by Wyndham Great Barrington Berkshires enjoy free WiFi in public areas, laundry facilities, and a vending machine. If you decide to drive, there's free parking. The front desk has multilingual staff that can help with dry cleaning/laundry and securing valuables. Additional amenities include barbecue grills, a picnic area, and a garden.
Pet friendly
Parking 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
Jan 1 - Jan 2, 2026
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

Pleasant Valley Motel West Stockbridge
42 Stockbridge Rd West Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
$52 nightly
The price is $57 total per night
$57 total
Jan 1 - Jan 2, 2026
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

Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $141 total per night
$141 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Vacation Village in the Berkshires features an indoor pool, an outdoor pool, and a children's pool. If you decide to drive, there's free parking. The front desk is staffed 24 hours a day to help with access to locker space and concierge services. Other amenities at this family-friendly condo building include a gym, free WiFi in public areas, and a business center.
Pool
Parking included

The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $103 total per night
$103 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests staying at The Yankee, Trademark Collection by Wyndham enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. 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 a hot tub, a seasonal outdoor pool, and coffee/tea in a common area.
Pool
Hot Tub
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.
The Berkshires hotels essential information
Accommodation | 1,084 hotels |
|---|---|
Lowest Price | $57 |
Highest Price | $462 |
Popular hotels | The Dewey, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Eastgate Inn B&B, Gateways Inn & Restaurant, Harbour House Inn, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, 1896 House Country Inn & Motels, The Orchards Hotel, The Red Lion Inn, Whistler's Inn Bed & Breakfast, Travelodge by Wyndham Great Barrington Berkshires, Monument Mountain Motel, Pleasant Valley Motel West Stockbridge, Vacation Village in the Berkshires, The Yankee, Trademark Collection by Wyndham |
Recent Hotels with a Wedding Venue Reviews

The Yankee, Trademark Collection by Wyndham
5/5 Excellent
"The room is so spotless, bathroom is so luxurious! The bed is so soft and sleep very quickly! The staffs are so great! Quick to answer to my questions and my needs. Definitely come back again to stay! "
A verified traveler stayed at The Yankee, Trademark Collection by Wyndham
Posted 5 days ago
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