Explore beach hotels in Stockbridge, MA from $96
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Top Stockbridge Beach Resorts & Hotels

The Red Lion Inn
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
$180 nightly
The price is $202 total per night from Nov 6 to Nov 7
$202 total
Nov 6 - Nov 7
Total with taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi ...
8.8/10 Excellent! (1,010 reviews)
"Great place! Food excellent ss well!"
Reviewed on Sep 30, 2025

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183, Stockbridge, MA
$335 nightly
The price is $374 total per night from Oct 20 to Oct 21
$374 total
Oct 20 - Oct 21
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast ...
"Very expensive for a small room. My son and I could barely sleep in this remote quiet place. Staffs were very friendly."
Reviewed on Nov 2, 2024
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.
Beach Condos in Stockbridge

UNIQUE - 1BR Country Condo @ Jiminy Peak
Hancock
$312 nightly
The price is $349 total per night from Oct 7 to Oct 8
$349 total
Oct 7 - Oct 8
Total with taxes and fees
9.8/10 Exceptional! (12 reviews)
Beach Villas in Stockbridge

Serene Farmhouse Villa: Pool + Hot Tub and Grill
Chatham
10/10 Exceptional! (1 review)
Your Stockbridge Beach Hotel Guide
Stockbridge Hotels on the Beach with the Amenities You Want
Stockbridge Beach Hotels with a Pool
- Blackberry River Inn is a 3.00 star hotel and previous guests rate it 3.60 out of 5.
- Hilton Garden Inn Lenox Pittsfield is a 3.00 star hotel and previous guests rate it 4.70 out of 5.
- Eastover Estate & Eco-Village is a 3.50 star hotel and previous guests rate it 3.60 out of 5.
Stockbridge Beach Hotels with Free Breakfast
- Stockbridge Country Inn is a 4.50 star hotel with a guest rating of 4.60 out of 5.
- Federal House Inn is a 3.50 star hotel with a guest rating of 4.80 out of 5.
- Whistler's Inn Bed & Breakfast is a 3.50 star hotel with a guest rating of 4.00 out of 5.
Pet-friendly Beach Hotels in Stockbridge
- Vacation Village in the Berkshires is a 3.00 star hotel with a guest rating of 4.20 out of 5.
- Thornewood Inn is a 3.50 star hotel with a guest rating of 3.60 out of 5.
- Cranwell Spa and Golf Resort is a 3.50 star hotel with a guest rating of 4.20 out of 5.
Stockbridge Beach Hotels with Restaurants
- Hotel On North is a 3.50 star hotel with a guest rating of 4.80 out of 5.
- Inn At Richmond is a 3.00 star hotel with a guest rating of 4.50 out of 5.
- The Old Inn On The Green is a 4.00 star hotel with a guest rating of 4.30 out of 5.
What are the cheapest hotels on the beach in Stockbridge
- Jiminy Peak Mountain Resort - Book Now
- Situated in the mountains, this condominium resort is 6.1 mi (9.8 km) from Mount Greylock State Reservation Visitor Center and within 12 mi (20 km) of Waubeeka Golf Links and New Lebanon Library. Mount Lebanon Shaker Village and Berkshire Athenaeum are also within 12 mi (20 km).
- 3.00 star rating.
- Harbour House Inn - Book Now
- 3.50 star rating.
- Stockbridge Country Inn - Book Now
- Situated in Stockbridge, this luxury bed & breakfast is within 1 mi (2 km) of Chesterwood and Norman Rockwell Museum. Berkshire Botanical Garden and Mission House are also within 2 mi (3 km).
- 4.50 star rating.
What’s better than a beautiful Stockbridge hotel near the beach? Finding that hotel for a deal! Check out our amazing deals on stunning Stockbridge beach hotel properties to find exactly what you’re looking for on your next trip to Stockbridge.
Cheapest Stockbridge Beach Hotels by Star Rating
Cheapest 4 Star Stockbridge Hotels on the Beach
- Yankee Suites Extended Stay: has a guest rating of 4.40 out of 5 stars.
- The Inn at Stockbridge: has a guest rating of 4.80 out of 5 stars.
- 1862 Seasons on Main Bed and Breakfast: has a guest rating of 5.00 out of 5 stars.
Cheapest 3 Star Stockbridge Hotels on the Beach
- Jiminy Peak Mountain Resort: has a guest rating of 4.00 out of 5 stars.
- Applegate Inn: has a guest rating of 4.50 out of 5 stars.
- Blackberry River Inn: has a guest rating of 3.60 out of 5 stars.
Best Oceanfront Hotels in Stockbridge, According to Traveler Reviews
- Book 33 Main, which has a guest rating of 5.00 out of 5 stars.
- Book 1862 Seasons on Main Bed and Breakfast, which has a guest rating of 5.00 out of 5 stars.
- Book Canterbury Farm, which has a guest rating of 5.00 out of 5 stars.
Popular Beach Stays in Stockbridge
Recent Stockbridge Hotel Reviews By Fellow Wanderers

The Black Swan Lee - Lenox, an Ascend Collection Hotel
5 out of 5
Posted 2 days ago
Travelocity Verified Review
"The location off the MA Pike is perfect. The woodwork and hallway carpets are dated but clean. The bedroom was clean and bed very comfortable. The surprise was the restaurant on premise, Mint. Best Indian food we have ever had! "
A verified traveler stayed at The Black Swan Lee - Lenox, an Ascend Collection Hotel
More Ways To Wander Stockbridge
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