A nighttime view of a residential area with houses adorned with holiday lights.

Find Family Hotels in Stockbridge, MA from CA $108

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Check availability on Stockbridge Family Hotels

Tonight
Sep 15 - Sep 16
Tomorrow
Sep 16 - Sep 17
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Stockbridge family-friendly hotels

1. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
CA $639
CA $1,189 total
includes taxes & fees
Oct 1 - Oct 2
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

2. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
CA $163
CA $209 total
includes taxes & fees
Sep 21 - Sep 22
Holiday Inn Club Vacations Oak 'n Spruce Resort

3. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
  • Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
CA $174
CA $194 total
includes taxes & fees
Sep 22 - Sep 23
The Black Swan Lee - Lenox, an Ascend Collection Hotel

4. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
Great Barrington
  • Escape with the kids to this quiet, comfortable motel where family stays come with free beds and cribs in immaculately clean rooms.
CA $104
CA $116 total
includes taxes & fees
Sep 17 - Sep 18
Travelodge by Wyndham Great Barrington Berkshires

5. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
Lee
  • Family-friendly budget escape with free miniature golf and breakfast, minutes from Berkshire Botanical Garden.
CA $96
CA $108 total
includes taxes & fees
Sep 22 - Sep 23
Econo Lodge Lee - Great Barrington

6. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
  • Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
CA $154
CA $172 total
includes taxes & fees
Oct 1 - Oct 2
Best Western Plus Berkshire Hills Inn & Suites

7. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
  • Families splash into fun at this Berkshires hotel with indoor pool, game arcade, and cozy rooms—all nestled near Ski Butternut.
CA $271
CA $302 total
includes taxes & fees
Sep 21 - Sep 22
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

8. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
CA $247
CA $276 total
includes taxes & fees
Sep 24 - Sep 25
Element by Marriott Lenox Berkshires

9. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
  • Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Centre.
CA $170
CA $190 total
includes taxes & fees
Sep 17 - Sep 18
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
  • Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
CA $160
CA $179 total
includes taxes & fees
Oct 15 - Oct 16
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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Choose what matters most at family-friendly hotels in Stockbridge

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Stockbridge Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"Bedding and bed were lovely. excellent to have good lighting at sink as well as a magnified mirror! Often lacking in places we have stayed. AC had trouble cooling the room down until we turned it on full blast. too much ambient light from floodlight on property next door and from hall (I finally turned off hallway light which helped. ) Common areas and halls need some brightening up with fresh, lighter paint--seemed dingy. Was terribly frustrating trying to make the Nespresso machine work. We do not own one and there were NO INSTRUCTIONS. You should assume people do not know how to operate any appliances like that and should have a card with directions. We gave up and went to the Tavern where we had lovely coffee and breakfast. Also had a great dinner in Tavern after our arrival. The patch burrata salad was superb. As was our waitress."
Judith 1-night trip
Posted 9 hours ago
The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Beds were comfortable but the pillows not so great but clean and quiet."
Sue 1-night trip
Posted 1 day ago
Quality Inn Great Barrington
Hotel On North

Hotel On North

10/10 Excellent
"Great location, clean room!"
Gayle 1-night trip
Posted 1 day ago
Hotel On North

Frequently asked questions

What are the best family-friendly hotels in Stockbridge?
If you're looking for a fantastic family-friendly hotel in Stockbridge, the Taggart River House is a impressive option that combines modern luxury with stunning natural beauty. With a stellar review rating of 9.8, this spacious property can accommodate up to ten guests, making it superb for larger families. Imagine waking up to breathtaking river views, and enjoying the convenience of onsite parking and a fully equipped kitchen, which is ideal for those family meals. The outdoor deck or patio is a lovely spot to relax while the kids play safely, thanks to amenities like a stair gate and travel crib.Another excellent choice is The Red Lion Inn, a charming 3.5-star hotel that has earned an excellent 8.8 rating from travellers. Nestled in a historic district, it offers a great experience enriched with character. Families will appreciate the connecting rooms and the complimentary crib for little ones. In winter, you can hit the nearby ski slopes or enjoy cross-country skiing lessons, making it a wonderful year-round destination. Guests rave about the comfortable and quiet rooms, along with the friendly service from the staff, not to mention the excellent food options available on-site.
Which area of Stockbridge is best to stay in for families?
For families visiting Stockbridge, the main village area around Main Street is the best place to stay, offering a central location with easy access to attractions and amenities.Staying in the heart of Stockbridge means you're just a short stroll from the Norman Rockwell Museum, which offers a fascinating glimpse into American life through his iconic illustrations – many of which depict scenes that resonate with children. The village green is a lovely spot for a picnic or simply letting the children run around, and you'll find several charming shops to browse.The walkability of this area is a huge plus for families; you can easily explore the village on foot without needing to rely on a car. There are also footpaths and quiet lanes superb for a gentle family walk or a pushchair outing.You'll find a selection of casual eateries along Main Street, many offering kid-friendly options, as well as quaint ice cream parlours for a sweet treat.
How much does a family hotel in Stockbridge cost?
Travellers can find great deals on family-friendly Stockbridge hotels from CA $108 with Expedia. You may find hotels in Stockbridge that let kids stay for free, which can help you save. There are plenty of factors that can impact the price of family hotels, including location, amenities and the time of year. Sort Stockbridge hotels on Expedia by price to see our cheapest prices first.
What are the best Stockbridge family-friendly hotels with a pool?
The Red Lion Inn is a charming 3.5-star hotel that families adore, particularly for its inviting outdoor pool. With a traveller rating of 8.8, guests frequently praise the comfortable and quiet rooms, along with the excellent food and friendly staff. Families appreciate the connecting rooms, making it easy for everyone to stay close while enjoying their own space.Located in a historical district, The Red Lion Inn offers a unique charm that can enhance your family adventure. Its proximity to outdoor activities, including skiing options nearby, adds to its appeal for families seeking a mix of relaxation and adventure. After a day of exploring, you can unwind by the pool, creating lasting memories with your loved ones.
Which cheap kid-friendly hotels in Stockbridge do travelers love?
Taggart River House is a delightful option for families seeking both affordability and comfort in Stockbridge. With its stunning river views, this charming property can accommodate up to ten guests, making it great for larger families.The house is well-equipped with family-friendly amenities, including a Travel Crib and a StairGate to ensure safety for younger children. The spacious kitchen allows you to prepare meals at your convenience, while the inviting deck or patio offers a lovely spot to unwind and enjoy the natural surroundings. Additionally, the onsite golf course provides a fun activity for the whole family.
Which Stockbridge family-friendly hotels welcome pets?
The Red Lion Inn is a charming 3.5-star family-friendly hotel in Stockbridge that warmly welcomes pets, making it a fantastic choice for those travelling with furry companions. With a traveller rating of 8.8, guests often praise the comfortable and quiet rooms, coupled with excellent service from the friendly staff.Located in a historical district, The Red Lion Inn offers connecting rooms and free cribs, ensuring convenience for families with children. For those interested in winter sports, the hotel is perfectly situated near various ski areas, allowing easy access to skiing and cross-country skiing adventures. After a day of exploring or hitting the slopes, families can enjoy the excellent food options available at the hotel, satisfying various palates.
Which family-friendly hotels are in central Stockbridge?
The Red Lion Inn is a charming 3.5-star hotel that perfectly embraces the family-friendly spirit in central Stockbridge. Nestled in a historical district, it offers a range of amenities that cater to families, including connecting rooms and free cribs, making it an ideal choice for those travelling with little ones. Guests consistently rave about the comfortable and quiet rooms, alongside the friendly and attentive staff, giving it an excellent review rating of 8.8.For those seeking a touch of modern luxury amidst nature, the Taggart River House is another fantastic option. With a stellar review rating of 9.8, this unique accommodation sleeps up to ten people and features stunning river views. Families will appreciate amenities like a travel crib, a fully equipped kitchen for convenient meal prep, and a lovely patio area to relax and enjoy the surroundings.Both hotels not only provide excellent service but also position you conveniently to explore the nearby ski areas, great for winter adventures.
Is Stockbridge a family-friendly destination?
Yes, Stockbridge is a wonderfully family-friendly destination, offering a charming mix of natural beauty, activities, and a relaxed atmosphere superb for a family holiday.The village itself is incredibly walkable, with picturesque streets lined with independent shops and lovely cafes. You'll find plenty of spots for a casual bite to eat, many of which are very welcoming to families. For a sweet treat, there are often delightful ice cream parlours.One of the main draws for families is the abundance of outdoor spaces. The River Test, which flows through the village, offers lovely riverside walks that are flat and easy for little legs or pushchairs. There are also several green spaces superb for a picnic or simply letting the children run around and play.Just a short drive away, you'll find the beautiful landscapes of the New Forest National Park, offering endless opportunities for walks, bike rides on designated paths, and exploring the great outdoors.
What family-friendly activities should we do in Stockbridge?
Some of the best family-friendly activities in Stockbridge include exploring the Berkshire Botanical Garden and enjoying the outdoors at the Laura's Tower Trail.The Berkshire Botanical Garden is a delightful place for families to wander and discover the wonders of nature. With various themed gardens, including a children's garden designed for interactive play and learning, it offers a peaceful and engaging experience. Kids will love the open spaces to roam and the colourful displays of plants.For those who enjoy a bit of an adventure, the Laura's Tower Trail offers a lovely walk through nature with a rewarding view at the top. It's a moderately easy hike that families can enjoy together, providing an opportunity for some fresh air and exercise amidst beautiful scenery. Remember to wear comfortable shoes.
How can I save on a family-friendly hotel in Stockbridge with Expedia?
There are plenty of ways to save on a family-friendly hotel in Stockbridge. Join One Key™, our free travel rewards program, to unlock instant discounts with Member Prices across a range of hotels. Typically, booking in advance will help you save on your family hotel booking. If you're feeling spontaneous, be sure to check for last-minute deals.
What are the best family hotels in Stockbridge that have a spa?
The Red Lion Inn is a charming 3.5-star hotel that seamlessly blends family-friendly amenities with a touch of relaxation. With an excellent traveller rating of 8.8, this hotel is a favourite among families looking for comfort and convenience.Guests appreciate the soothing onsite spa, where you can indulge in rejuvenating massages after a day of exploring. The Red Lion Inn also offers connecting rooms, making it easy for families to stay close together. Located in a historical district, it provides an enriching experience, superb for families wanting to learn more about the area's heritage.In addition to its relaxing spa services, the hotel is well situated for outdoor adventures, with nearby ski rentals and lessons, suiting both winter sports enthusiasts and those simply looking to enjoy the beautiful Massachusetts landscape.
Are there any great family hotels in Stockbridge with a gym?
The Red Lion Inn is a charming 3.5-star family-friendly hotel that offers a delightful experience for visitors in Stockbridge. Nestled in a historic district, this hotel not only provides comfortable and quiet rooms but also features excellent dining options that travellers rave about.For families looking to stay active during their holiday, The Red Lion Inn boasts fitness facilities, ensuring you can keep up with your workout routine even while away from home. With a review rating of 8.8, guests frequently compliment the friendly staff and the quality of service they receive, further enhancing the welcoming atmosphere of the hotel.Additionally, the location is ideal for adventurous families, as it's close to various skiing opportunities nearby, superb for winter sports enthusiasts.
Can I cancel my family hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right family-friendly hotel in Stockbridge for you.

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