Romantic Hotels in Stockbridge, MA
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Featured Stockbridge Romantic Getaways & Hotels
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 7 - Jan 8, 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
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
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.
Couples getaways in Stockbridge
Nothing says romance like a spontaneous trip away to someplace stylish. Whether you need a relaxing weekend getaway to escape the ankle biters and regain that passion or you're seeking a gorgeous honeymoon destination, there's bound to be something in Stockbridge for you.
Romantic places to visit in StockbridgeRomance, adventure and glorious memories — it's all there for the taking when you bring your significant other to these alluring attractions:
- Looking to take your love someplace different while you're here? A day out at Berkshire Theatre Festival will surely impress!
- Another attraction well worth noting on your itinerary is Naumkeag. Many starry-eyed couples have enjoyed spending time there.
- Why not take a look around Norman Rockwell Museum while you're out and about in the area? It's a hit with both locals and tourists.
- Finally, if you have some extra time up your sleeve, you and your beloved really ought to stop by Schantz Galleries.
Stockbridge hotels essential information
Accommodation | 1,347 hotels |
|---|---|
Lowest Price | $198 |
Highest Price | $462 |
Popular hotels | The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, The Red Lion Inn |
Recent Romantic Getaways & Hotels 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 3 days ago
