Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

William Keller on trover

Search for Stockbridge Hotels

Filter by

Selecting an option opens a search results page with the selected filter applied
Popular FiltersSelecting an option opens a search results page with the selected filter applied
Star ratingSelecting an option opens a search results page with the selected filter applied
Your BudgetSelecting an option opens a search results page with the selected filter applied
Guest ratingSelecting an option opens a search results page with the selected filter applied
Payment TypeSelecting an option opens a search results page with the selected filter applied
Property TypeSelecting an option opens a search results page with the selected filter applied
AreaSelecting an option opens a search results page with the selected filter applied
Popular LocationsSelecting an option opens a search results page with the selected filter applied
AmenitiesSelecting an option opens a search results page with the selected filter applied
AccessibilitySelecting an option opens a search results page with the selected filter applied
Trip TypeSelecting an option opens a search results page with the selected filter applied
Completely Renovated Historic Home in the Heart of the Berkshires
Get Rates
2.32 km from city centre
5/5Exceptional! (11 reviews)
Loved this home!

"We really enjoyed our too short stay. The home had all the amenities and comfort needed for a wonderful weekend. We will definitely be back!"…"

Reviewed on Jan. 22, 2020

Completely Renovated Historic Home in the Heart of the Berkshires
Greek Revival Style Farmhouse Circa 1820
12 Glendale Road, Stockbridge, MA
Get Rates
2.18 km from city centre
4.9/5Exceptional! (33 reviews)
Wonderful, charming house

"6 of us stayed for 2 nights at this beautiful property. It was immaculate! The owner had coffee and bread waiting for us when we arrived. It was very comfy and cozy and we spent our evenings around the fire playing games and talking. Very quick drive to Stockbridge and W Stockbridge. Don’t miss the ..."…"

Reviewed on Feb. 24, 2020

Greek Revival Style Farmhouse Circa 1820
Beautiful Home in Great Location!- Sleeps 13!
39 Main Street, Stockbridge, MA
Get Rates
0.93 km from city centre
Beautiful Home in Great Location!- Sleeps 13!
  • You could be seeing lower prices

    With member prices, you could save 10% or more right now on thousands of properties.
    Sign up, it's freeSign in
Enchanting Stockbridge House With Heated Pool!
12 Prospect Hill, Stockbridge, MA 01262, Stockbridge, MA
Get Rates
0.65 km from city centre
Enchanting Stockbridge House With Heated Pool!
Holiday in Norman Rockwell's Stockbridge
68 Main St, Stockbridge, MA
Get Rates
1.21 km from city centre
4.6/5Wonderful! (5 reviews)
centrally located

"convenient walkable location to downtown Stockbridge. easy access by car to all Berkshire sites like Jacobs Pillow and Tanglewood."…"

Reviewed on Aug. 27, 2019

Holiday in Norman Rockwell's Stockbridge
General Williams Estate House Lenox/stockbridge
Get Rates
2.64 km from city centre
4.8/5Exceptional! (50 reviews)
Fifth time’s the charm

"Starting coming here five years ago for our fortieth birthday with a group of our closest friends. This was our fifth year of what has become an annual tradition that we all look forward. The house is perfect for hanging out with family and friends. The proximity to shops and restaurants is perfect. ..."…"

Reviewed on Jan. 12, 2020

General Williams Estate House Lenox/stockbridge
Modern New England Farmhouse on Prospect Hill
22 B Prospect Hill Rd, Stockbridge, MA
Get Rates
1.01 km from city centre
Modern New England Farmhouse on Prospect Hill
Pristine 2 Bedroom Suite in Amazing Location!
Get Rates
0.93 km from city centre
Pristine 2 Bedroom Suite in Amazing Location!
A Grand Estate in Historic Stockbridge
18 Main Street, Stockbridge, MA
Get Rates
0.69 km from city centre
4.9/5Exceptional! (39 reviews)
Magnificent Place for a Pandemic Family Weekend Getaway

"Not expecting a pandemic, I reserved The Taggart House to meet my mom and 4 adult kids (plus one significant other) for some family bonding in April. The owners graciously allowed us to reschedule for June, so we stayed this past Friday through Monday. The owner Caitlin welcomed us on our arrival. ..."…"

Reviewed on Jun. 11, 2020

A Grand Estate in Historic Stockbridge
Rabbit Run - in the Heart of Stockbridge
78 E Main St, Stockbridge, MA
Get Rates
1.57 km from city centre
Rabbit Run - in the Heart of Stockbridge
Available for Summer 2020 Stockbridge Home Minutes From Tanglewood
Get Rates
1 km from city centre
5/5Exceptional! (2 reviews)
Heaven in the woods!

"The house/home surpassed expectations! Comfortable, roomy, cozy...and gorgeous woodsy and grassy surroundings! My family loved it, too! A perfect getaway-hideaway gem!!"…"

Reviewed on Sep. 5, 2019

Available for Summer 2020 Stockbridge Home Minutes From Tanglewood
Two Blocks From the Red Lion Inn & Next to Berkshire Theater
Get Rates
1.42 km from city centre
4.7/5Exceptional! (3 reviews)
Peaceful Home

"A wonderful 3-night stay in Joanna and Warren’s light-filled, clean and peaceful barn converted into a wonderful home. We enjoyed every room in the house-comfortable beds, spacious bathrooms, kitchen with everything, sunroom perfect for reading and a dining room table just right for games. When we ..."…"

Reviewed on Jun. 17, 2019

Two Blocks From the Red Lion Inn & Next to Berkshire Theater
Stockbridge One Of The Finest Homes and Best Locations... Walk To Beach
Get Rates
3.44 km from city centre
5/5Exceptional! (41 reviews)
Amazing Stay

"Excellent Host. Very responsive. Beautiful house with all the amenities you could ask for. Great location!!!"…"

Reviewed on Jul. 5, 2020

Stockbridge One Of The Finest Homes and Best Locations... Walk To Beach
Family-friendly Cottage Off Lake in Stockbridge
11 Mahkeenac Heights Road, Stockbridge, MA
Get Rates
4.46 km from city centre
4.9/5Exceptional! (15 reviews)
Nice Cottage

"We had a pleasant stay. The house was very clean. Everything IKEA. Very stylish. Interesting contrast to this quaint rustic summer cottage. Very well stocked. Had to use the space heaters at night but that was expected. The Stockbridge beach was amazingly beautiful! The location of the house is perfect. ..."…"

Reviewed on Oct. 14, 2019

Family-friendly Cottage Off Lake in Stockbridge
PRIVATE_VACATION_HOME
Address Provided by Property Manager, Bouvet Island
Get Rates
4.2 km from city centre
PRIVATE_VACATION_HOME
Don't see what you're looking for?
See all available properties in Stockbridge
View all properties
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 Guide

You will find yourself spoiled for choice when it comes to finding quality hotels in Stockbridge. On Expedia's up-to-the-minute booking pages you can browse 37 accommodation choices within a 0.1-kilometre (0.06-mile) radius of Stockbridge's heart.

Why not book a room close to the heart of Stockbridge? The The Cottage B&B and The Red Lion Inn are conveniently located 1 kilometre (0.6 miles) of the city's downtown.

The Rookwood Inn is located 8 kilometres (5 miles) from the main part of Stockbridge. Alternatively, the Gateways Inn & Restaurant is 8 kilometres (5 miles) away. Some other accommodation options are the Hampton Terrace Inn and the Cranwell Spa and Golf Resort.

50 kilometres (30 miles) to the north of Stockbridge is Williamstown, where you can find Williams College and Williams College Museum of Art. The The Orchards Hotel and House On Main Street are a few of the great hotel and apartment options in Williamstown. Alternatively, you could consider staying at Lee, 6 kilometres (4 miles) to the east of Stockbridge, where you can pick from the Federal House Inn and Black Swan Inn, an Ascend Collection Hotel. Should you choose to stay in Lee, set aside some time to visit the Lee Prime Outlets and Tyringham Cobble.

Why not spend an afternoon cheering along with The Berkshires sports enthusiasts at a local match. You'll find Times Union Center 55 kilometres (33 miles) to the northwest of Stockbridge. Those sports fans wishing to find a room or apartment nearby can make a choice from the Hilton Albany or the TownePlace Suites by Marriott Albany Downtown/Medical Center.

Albany International Airport is a logical airport for flying in and out of Stockbridge. It is 65 kilometres (40 miles) drive away. If you would like to stay nearby, try the Residence Inn by Marriott Albany Airport or The Desmond Hotel Albany.

Frequently asked questions

Where is the best place for a stay in Stockbridge?
The Red Lion Inn is one of the top choices for your stay based on our traveler data. This 3.5-star hotel offers 3 restaurants and an outdoor pool. Other good choices for your stay include Tanglewood Suites and The Inn at Stockbridge.
If I need to cancel my hotel reservation in Stockbridge, will I receive a refund?
Yes! You’ll find that most hotel room reservations are fully refundable as long as you cancel prior to the hotel’s cancellation deadline, which is often 24 or 48 hours before check in. If you have a non-refundable reservation, you might be able to cancel it and get a refund within a 24-hour period of your booking. Enter your dates, click on “Search”, then filter by “free cancellation” to get the best deals available in Stockbridge.
What's the best accommodation for a romantic vacation to Stockbridge?
1862 Seasons on Main Bed and Breakfast is a favorite 4.5-star B&B for couples, and features premium bedding and a restaurant. Other good choices for a stay with your sweetheart include The Red Lion Inn and Stockbridge Country Inn.
What's the best pet-friendly accommodation in Stockbridge?
The Inn at Stockbridge is a top dog-friendly B&B, and offers an outdoor pool and a fitness center for its human guests.
What's the best accommodation for a beach vacation in Stockbridge?
The Red Lion Inn is a top 4.5-star B&B for a beach vacation, and features free breakfast and free WiFi. Other good choices to stay near the beach include Stockbridge Country Inn and The Red Lion Inn. Spend some quality time by the water at Iroquis Waterfront.
What's the best high-end place to stay in Stockbridge?
Stockbridge Country Inn is a 4.5-star B&B with a seasonal outdoor pool and private balconies, and it’s a popular choice for Expedia travelers looking for an elegant place to stay. Another upscale choice for your vacation is 1862 Seasons on Main Bed and Breakfast.
What's the best boutique hotel in Stockbridge?
1862 Seasons on Main Bed and Breakfast is a favorite 4.5-star B&B with Expedia travelers looking for a stylish accommodation, featuring a restaurant and spa services.
What's the best accommodation in Stockbridge to absorb the local history?
Based on our travel expertise, The Red Lion Inn is a top 3.5-star historic hotel bookable on Expedia and it offers 3 restaurants. Other choices close to historic sites include 1862 Seasons on Main Bed and Breakfast and Stockbridge Country Inn. Also notable landmarks to visit include National Shrine of the Divine Mercy, Naumkeag, and Mission House.
What's the best place to stay to stay near the slopes in Stockbridge?
Based on our travel data, Conroy’s B&B is a top 3.5-star B&B for hitting the ski slopes, and features free breakfast and an outdoor pool. Other good choices for your ski trip include Stockbridge Country Inn and The Red Lion Inn. Enjoy the skiing and snowboarding by visiting Ski Butternut or Catamount Ski Area.

Recent Reviews in Stockbridge

More trip options