The Best Hotels with a Pool in South Lee, MA from ￥18,132 in 2026

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Our top choices for South Lee hotels with a pool

2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers

1. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.

￥27,029 total

includes taxes & fees

Aug 31 - Sep 1

2. The Red Lion Inn

Stockbridge

Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.

￥39,701 total

includes taxes & fees

Aug 31 - Sep 1

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

Great Barrington

Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.

￥34,703 total

includes taxes & fees

Aug 24 - Aug 25

4. 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.

￥28,526 total

includes taxes & fees

Aug 23 - Aug 24

5. Sunset Inn

Lee

Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.

￥18,132 total

includes taxes & fees

Aug 24 - Aug 25

Superior Room, 1 King Bed, Jetted Tub | Desk, laptop workspace, iron/ironing board, WiFi (free)

6. The Yankee Inn

Lenox

Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.

￥25,352 total

includes taxes & fees

Aug 2 - Aug 3

7. The Little Lion

Great Barrington

Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.

￥22,462 total

includes taxes & fees

Aug 4 - Aug 5

8. Devonfield Inn B&B

Lee

Escape to an elegant countryside retreat with an inviting outdoor pool, premium spa services, and made-to-order gourmet breakfast.

￥72,917 total

includes taxes & fees

Aug 27 - Aug 28

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Choose what matters most at hotels with a pool in South Lee

Breakfast included

4 stars

Top South Lee Hotel Reviews

The Red Lion Inn

8/10 Good

"I gotta admit, I was nervous about staying at the Red Lion Inn. I knew it was popular, but I stayed in their "sister" place (the Little Lion) once because it was the only available hotel room in the area at short notice and that place is a DISASTER. However, now I understand why people who love the Red Lion Inn LOVE the Red Lion Inn. It's not pristine & shiny in a new hotel kinda way. But it's also the exact opposite of a bland, chain hotel with no character or interest. 250y of history pours out of every inch of this place, and in a good way. I didn't get a chance to take advantage of the gym, pool, or other amenities, though did eat in the courtyard one lunchtime and that was good. The staff are very attentive and appear to take real pride in working in such an iconic hotel. My only criticism is that I don't think the cleaning is quite up to scratch. Harder to clean 250yo hotel with rugs over ancient wood floors than a new construction with LVP, but findings long blonde hairs on my hotel room wasn't something I enjoyed (my entire family is either red or brunette). Would I stay there again? Yes. Room prices in the summer are insane, like most places in the Berkshires, but that's when I have to go to the Berkshires, so if they don't get my business in the future, it'll be because there are no rooms available or for some reason a different town is a better choice of location, not because I don't want to stay here. 1 word of warning: have dog? Call to make your reservation."

Vacation Village in the Berkshires

8/10 Good

"While not a top-notch place to stay, for the price it is a good value particularly given that you have more space for less cost than just a good motel room and can do some cooking and meal prep on your own. The check-in is always smooth and the accommodations reasonably comfortable. Setting is very nice, particularly if you get a room/suite that isn't looking onto the parking lot/driveway area. We continue to stay here, even though every stay finds something that wasn't caught in the room clean-up but not really a housekeepers problem - this time it was a failing toaster and a micro-wave that wanted to make a noise all the time."

Jiminy Peak Mountain Resort

10/10 Excellent

"Excellent "get away from it all" vibe on this little mountain resort. The drive and area is wooded and beautiful. The staff is AMAZING! Helpful, friendly, warm and welcoming. The rooms were cute and clean. Maybe a little dated and worn, but for the price they are perfect!! The pool was a bit small, but not crowded and deep. We also really enjoyed the walking trails, tennis court and pickle ball court. The adventure park was excellent for active kids. The ski lift ride was great and the alpine slide and mountain coaster is great for the whole family regardless of age!"

Frequently asked questions

What's it like visiting South Lee?

If lounging by a pool is your idea of the perfect getaway, you may want to consider luxurious South Lee, which has 17 places to stay with pools. During your visit, you can explore sights such as Housatonic River and National Shrine of the Divine Mercy, and then relax and unwind poolside at one of the accommodations in South Lee that guests like for their pools.

What are some accommodations with pools in South Lee?

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Vacation Village in the Berkshires: Offers a sauna, a communal pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Provides a children's pool, an indoor pool, and free self parking. Quality Inn Great Barrington: Features free self parking, an indoor pool, and complimentary wireless internet access. The Yankee Inn: Features a seasonal outdoor pool, an indoor pool, and buffet.

How many pool hotels will I be able to find in South Lee?

Expedia's 17 hotels in South Lee give you a great choice for your poolside getaway.

What is there to see and do in South Lee?

The picturesque setting of Housatonic River showcases the area's natural beauty. Discover sights such as Chesterwood during your stay. You'll also discover lost of options for restaurants and cheese shops in South Lee.

When is the best time to book a hotel with a pool in South Lee?

Taking into account the local weather in South Lee can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in South Lee are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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Check availability on South Lee Hotels with a Pool

Our top choices for South Lee hotels with a pool

1. Holiday Inn Club Vacations Oak 'n Spruce Resort

2. The Red Lion Inn

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

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

5. Sunset Inn

6. The Yankee Inn

7. The Little Lion

8. Devonfield Inn B&B

9. The Inn at Stockbridge

10. Little Cat Lodge

Choose what matters most at hotels with a pool in South Lee

Top South Lee Hotel Reviews

The Red Lion Inn

The Yankee Inn

Vacation Village in the Berkshires

Quality Inn Great Barrington

Jiminy Peak Mountain Resort

Howard Johnson by Wyndham Lenox

Frequently asked questions

Explore a world of travel with Expedia

Find Hotels with a Pool in South Lee, MA

Change your mind

Treat yourself

Be picky

Check availability on South Lee Hotels with a Pool

Our top choices for South Lee hotels with a pool

1. Holiday Inn Club Vacations Oak 'n Spruce Resort

2. The Red Lion Inn

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

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

5. Sunset Inn

6. The Yankee Inn

7. The Little Lion

8. Devonfield Inn B&B

9. The Inn at Stockbridge

10. Little Cat Lodge

Choose what matters most at hotels with a pool in South Lee

Top South Lee Hotel Reviews

The Red Lion Inn

Frequently asked questions

Explore a world of travel with Expedia