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Top Stockbridge hotels

Historic Stockbridge Villa on 25 acres sleeps 23

Historic Stockbridge Villa on 25 acres sleeps 23

Stockbridge MA
This vacation home features an outdoor pool and a sauna. Families will appreciate the playground and barbecue grills. A garden and laundry facilities are also ...
"Great home, warm and welcoming!! Hosts were great! Very attentive, enjoyed meeting Lisa. Plenty of room for our gathering, accommodations were excellent!"

Reviewed on Jan 25, 2026

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Opens in a new windowHistoric Stockbridge Villa on 25 acres sleeps 23
The Inn at Stockbridge

The Inn at Stockbridge

4 out of 5
30 East Street Stockbridge MA
$389 nightly
The price is $435 total per night from Jul 26 to Jul 27
$435 total
Jul 26 - Jul 27
Total with taxes and fees
This bed & breakfast features a 24-hour gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free ...
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."

Reviewed on Nov 24, 2025

Opens in a new windowThe Inn at Stockbridge
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
26 Glendale Road, RR 183 Stockbridge MA
$358 nightly
The price is $399 total per night from Aug 5 to Aug 6
$399 total
Aug 5 - Aug 6
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 ...
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."

Reviewed on Jul 14, 2026

Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $195 total per night from Jul 28 to Jul 29
$195 total
Jul 28 - Jul 29
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. ...
"The Inn is a bit older but well maintained. The outdoor and indoor pools were lovely. The bed was comfortable with adequate bedding. Our bathtub was quite outdated but the rest was updated and fine. I would stay again - Good value and excellent location to Lenox and attractions."

Reviewed on Jul 23, 2026

Opens in a new windowThe Yankee Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $158 total per night from Aug 23 to Aug 24
$158 total
Aug 23 - Aug 24
Total with taxes and fees
This aparthotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self ...
"The floor around the pool was peeling back by about a foot, despite the pictures, paint was peeling off the walls in our bathroom, the fan wasn’t functional in the bathroom either, and the room smelled super musty like it hadn’t been air out in weeks."

Reviewed on Jul 23, 2026

Opens in a new windowBerkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $170 total per night from Aug 23 to Aug 24
$170 total
Aug 23 - Aug 24
Total with taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby ...
"The HVAC unit in our room was loud. We couldn't find a way to quiet it or adjust the thermostat so that it ran less often."

Reviewed on Jul 22, 2026

Opens in a new windowBerkshires Untold
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $150 total per night from Aug 18 to Aug 19
$150 total
Aug 18 - Aug 19
Total with taxes and fees
This aparthotel features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym ...
"Clean room and spacious accommodations."

Reviewed on Jul 22, 2026

Opens in a new windowVacation Village in the Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundable
$118 nightly
The price is $132 total per night from Aug 13 to Aug 14
$132 total
Aug 13 - Aug 14
Total with taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. ...
"We have stayed here every time we go to Tanglewood. The service is always friendly, the price is reasonable and central to everything in Great Barrington. Highly recommend."

Reviewed on Jul 22, 2026

Opens in a new windowQuality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
$223 nightly
The price is $249 total per night from Jul 27 to Jul 28
$249 total
Jul 27 - Jul 28
Total with taxes and fees
This historic hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in ...
Opens in a new windowThe Red Lion Inn
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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.

Stockbridge Hotel & Travel Guide

Stockbridge offers visitors a broad selection of ideal hotel and apartment possibilities to select from. Travelocity's booking page currently is where modern travelers can compare 37 establishments within a 6-mile (10-kilometer) distance of Stockbridge's urban core.

Scouring the internet for a place to lay your head close to the bright lights of inner-city Stockbridge has been made so easy. Our easy to use booking page features the The Cottage B&B and The Red Lion Inn, which await your arrival within a radius of 0.6-mile (1-kilometer) of the urban center.

The Rookwood Inn can be found about 5 miles (8 kilometers) from central Stockbridge. Another place to stay is the Gateways Inn & Restaurant, which is located about 5 miles (8 kilometers) away. Some other hotels include the Hampton Terrace Inn and the Cranwell Spa and Golf Resort.

Once you and your traveling partner have got to know Stockbridge, why not tour a little bit more of the region? The Western Massachusetts region has countless things to offer visitors. Get to know Western Massachusetts's history museums and fall in love with the area's mountains. In this fascinating part of United States of America visitors may also partake in skiing, cross-country skiing and mountain biking.

Lanesborough is 18 miles (29 kilometers) north of Stockbridge and features Mount Greylock State Reservation Visitor Center and Skyline Country Club. The The Weathervane Motel and Lanesborough Country Inn are a few of the Travelocity long and short-stay alternatives in Lanesborough. 25 miles (42 kilometers) north of Stockbridge, you'll reach Williamstown, which is home to the The Spring's Inn and Berkshire Hills Country Inn. If you visit Williamstown, make sure you visit the Williams College and Williams College Museum of Art.

If you think of sport as your life and enjoy watching local matches you and your family could visit Times Union Center, found 35 miles (54 kilometers) to the northwest of Stockbridge. Wise visitors that need to find accommodation options close by can read about the Hilton Albany or the TownePlace Suites by Marriott Albany Downtown/Medical Center.

Albany International Airport is a major entry point for those flying into and leaving Stockbridge. You can find it 40 miles (65 kilometers) from the town center. For travelers who would like to stay close by, check out Albany Marriott or Homewood Suites by Hilton Albany.

Frequently asked questions

What are the top kid-friendly hotels in Stockbridge?
Family getaways are where the best memories are made, but traveling with little ones can be a challenge. These kid-friendly Stockbridge hotels come with perks designed to keep travelers of all ages relaxed and happy: Tanglewood Suites will help make your next trip the best one yet. It comes with a range of nice little touches, such as complimentary breakfast and an outdoor entertainment area. Also consider A Grand property in Historic Stockbridge. It comes with animal viewing activities, a king bed and lots of opportunities to spend time together.
Where can I find cheap hotels in Stockbridge?
At Travelocity you'll find really nice hotels in Stockbridge at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Stockbridge rather than in Stockbridge. We may find you even better rates, too.
How do I find the best Stockbridge hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Stockbridge then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Stockbridge?
The cheapest hotel in Stockbridge is $132. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Stockbridge?
There are 1,339 hotels in Stockbridge on Travelocity.
What are the best hotels in Stockbridge?
Stockbridge has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Stockbridge for you!
When is the best time to visit Stockbridge?
If you want the joy of a fun-filled trip in peak season, visit Stockbridge during February, March and April. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Stockbridge?
Based on historic data is usually the cheapest month to visit Stockbridge. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Stockbridge?
There are multiple hotels in Stockbridge that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Stockbridge. We have plenty of kid-friendly hotels in Stockbridge to choose from on Travelocity!
Why book a hotel in Stockbridge through Travelocity?
Because we have the top hotels in Stockbridge! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Stockbridge on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Stockbridge hotel reviews by fellow wanderers

The Yankee Inn

The Yankee Inn

4 out of 5
Posted 1 hour ago
Travelocity Verified Review
"The Inn is a bit older but well maintained. The outdoor and indoor pools were lovely. The bed was comfortable with adequate bedding. Our bathtub was quite outdated but the rest was updated and fine. I would stay again - Good value and excellent location to Lenox and attractions."
A verified traveler stayed at The Yankee Inn
The Yankee Inn

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