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

Find Hotels with a Pool in Stockbridge, MA

Check availability on Stockbridge Hotels with a Pool

Tonight
Aug 17 - Aug 18
Tomorrow
Aug 18 - Aug 19
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Stockbridge hotels with a pool

Outdoor pool, sun loungers
Exterior
Exterior
Property grounds

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
$198 nightly
$221 total
Sep 17 - Sep 18
Total with taxes and fees
The Red Lion Inn
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers
Lobby sitting area
Suite, Private Bathroom (Parlour Suite) | Premium bedding, iron/ironing board (on request), WiFi (free)
Free daily continental breakfast

2. 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
Stockbridge
  • Seasonal outdoor pool retreat at this colonial b&b invites lounging amid gardens and historic charm.
$358 nightly
$399 total
Aug 31 - Sep 1
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Seasonal outdoor pool
Front of property
Gilded Stage in the Mainhouse | Bathroom | Designer toiletries, hair dryer, towels, soap
Exterior

3. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
  • Seasonal outdoor pool beckons for refreshing summer dips at this upscale bed and breakfast in Stockbridge.
$396 nightly
$442 total
Sep 13 - Sep 14
Total with taxes and fees
The Inn at Stockbridge
2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers
Grand Villa, 3 Bedrooms | Iron/ironing board, cribs (free), WiFi, bed sheets
Grand Villa, 3 Bedrooms | Iron/ironing board, cribs (free), WiFi, bed sheets
Property amenity

4. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
$135 nightly
$150 total
Sep 8 - Sep 9
Total with taxes and fees
Holiday Inn Club Vacations Oak 'n Spruce Resort
Indoor pool
Lobby lounge
Premium bedding, pillowtop beds, in-room safe, desk
Free daily buffet breakfast

5. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
  • Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
$123 nightly
$137 total
Sep 15 - Sep 16
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior
Exterior
Front of property
Room, 1 Queen Bed, Mobility Accessible | Bathroom | Shower, free toiletries, hair dryer, towels

6. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
$105 nightly
$118 total
Sep 1 - Sep 2
Total with taxes and fees
The Little Lion
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers
Superior Room, 1 King Bed, Jetted Tub | Jetted tub
Superior Room, 1 King Bed, Jetted Tub | Desk, laptop workspace, iron/ironing board, WiFi (free)
View from room

7. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
$158 nightly
$176 total
Sep 14 - Sep 15
Total with taxes and fees
The Yankee Inn
Indoor pool
Exterior
Lobby
Lobby

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$125 nightly
$139 total
Aug 31 - Sep 1
Total with taxes and fees
Berkshire Mountain Lodge
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers
Exterior
Free daily buffet breakfast
One King Bed, Non-Smoking, Accessible Roll in shower | Bathroom shower

9. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
  • Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
$130 nightly
$146 total
Sep 14 - Sep 15
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Seasonal outdoor pool
Deep soaking bathtub
Basic Double Room | Blackout drapes, iron/ironing board (on request), WiFi (free)
Interior

10. Sunset Inn

Sunset Inn
Lee
  • Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
$108 nightly
$120 total
Sep 2 - Sep 3
Total with taxes and fees
Sunset Inn
View all properties

Choose what matters most at hotels with a pool in Stockbridge

Breakfast included
Hot tub
4 stars
Spa
5 stars

Top Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Place was clean and well equipped, pool and amenities were great too !"
Nyra 3-night trip
Posted 8 hours ago
Vacation Village in the Berkshires
The Inn at Stockbridge

The Inn at Stockbridge

10/10 Excellent
"This is an amazing place. A family-run Inn, with beautiful rooms, excellent breakfast food, and a beautifully maintained property with all the amenities I could want. I was particularly impressed with the shower, it had a massaging water flow that I have never seen before. I was also impressed with the lemon ricotta pancake special, the first morning I was there. I will definitely be back!"
Megan 2-night trip
Posted 13 hours ago
The Inn at Stockbridge
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"0nly 1 of 3 elevators was working. It was a 11 story building, and there was a lot of waiting. My room was wonderful, very clean, and with a fabulous view."
Linda 1-night trip
Posted 16 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"Very nice, clean, good breakfast. Only complaint was that it was very expensive because we booked last minute and it the peak season. I would stay again but not at the price we were charged."
Josephine 2-night trip
Posted 17 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Great hotel for a reasonable price. The only drawback is that they didn’t offer shampoos and body wash like most hotels but otherwise a great value."
Sheila 1-night trip
Posted 3 days ago
Howard Johnson by Wyndham Lenox
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Only problem was the stairs. I hadn't realized that there was such a long climb to our condo or I would have asked for something a little friendlier to a 75 year old."
Laura 1-night trip
Posted 4 days ago
Jiminy Peak Mountain Resort
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

10/10 Excellent
"Very lovely beautiful Room and property The outside pool was not available"
John 3-night trip
Posted 3 weeks ago
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Frequently asked questions

What are the best hotels in Stockbridge with outdoor pools?
The Red Lion Inn is a charming 3.5-star hotel that offers an inviting outdoor pool, great for families looking to unwind after a day of adventure in the beautiful Berkshires. Guests rave about the comfortable and quiet rooms, as well as the excellent food and friendly service provided by the staff. Plus, its prime location in a historic district means you're just a stone's throw away from local attractions, including nearby ski areas for winter sports enthusiasts.For a more intimate experience, consider The Stockbridge Country Inn, rated 4.5 stars by travellers. This delightful bed and breakfast not only features an outdoor pool but also provides complimentary full and continental breakfasts, ensuring a great start to your day. With its proximity to the Norman Rockwell Museum and picturesque mountain views, it's an ideal spot for families seeking both relaxation and cultural enrichment. Guests particularly appreciate the peaceful atmosphere and the opportunity for mountain biking right on-site.
How much does a hotel with outdoor pool in Stockbridge cost?
Enjoy staying in a hotel in Stockbridge with an outdoor pool. You can find a great deal from $118 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Is it cheaper to book flights and a Stockbridge hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember 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 hotel in Stockbridge for you.

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