South Lee Vacation Rentals from $139: Search Short-Term Rentals

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Our top choices for South Lee vacation rentals

1. Berkshire Mountain Lodge

Pittsfield

Robert

$125 nightly

Aug 31 - Sep 1

Total with taxes and fees

2. stylish Berkshires Retreat

Lee

Donna K.

$362 nightly

Sep 14 - Sep 15

Total with taxes and fees

3. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

$269 nightly

Sep 8 - Sep 9

Total with taxes and fees

4. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Peter S.

$286 nightly

Sep 1 - Sep 2

Total with taxes and fees

Beach nearby, sun loungers, beach towels

5. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Great Barrington

Kristin O.

$241 nightly

Sep 13 - Sep 14

Total with taxes and fees

4 bedrooms, travel crib, WiFi, bed sheets

6. Stylish Mid-century Modern Berkshires Cape

Lee

H B.

$782 nightly

Sep 2 - Sep 3

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

7. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Joanna P.

$245 nightly

Sep 9 - Sep 10

Total with taxes and fees

8. Spacious Central Berkshires Home for Groups

Lee

Beth S.

9. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

$557 nightly

Sep 14 - Sep 15

Total with taxes and fees

10. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

$367 nightly

Sep 9 - Sep 10

Total with taxes and fees

11. Historic Stockbridge Villa on 25 acres

Stockbridge

Amy M.

$975 nightly

Aug 17 - Aug 18

Total with taxes and fees

12. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

$271 nightly

Sep 13 - Sep 14

Total with taxes and fees

13. Home in Great Barrington

Great Barrington

HEATHER G.

$364 nightly

Aug 24 - Aug 25

Total with taxes and fees

14. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

$365 nightly

Aug 19 - Aug 20

Total with taxes and fees

Desk, iron/ironing board, WiFi, bed sheets

15. The Brooks Motel: Exceptional Suite

Hillsdale

Joan

$172 nightly

Aug 17 - Aug 18

Total with taxes and fees

16. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Dalton

Megan A.

$293 nightly

Aug 31 - Sep 1

Total with taxes and fees

17. Vacation Village in the Berkshires

Williamstown

peter

$128 nightly

Aug 31 - Sep 1

Total with taxes and fees

18. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

$241 nightly

Sep 9 - Sep 10

Total with taxes and fees

19. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Hancock

Jen B.

$241 nightly

Aug 19 - Aug 20

Total with taxes and fees

3 bedrooms, iron/ironing board, WiFi, bed sheets

20. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

Mary R.

$599 nightly

Sep 14 - Sep 15

Total with taxes and fees

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Top South Lee Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"The room was clean and the beds comfortable. The bathroom was small but nice. Lots of construction in the parking areas but luckily we got a parking space. Staff was friendly and helpful. We ate at the hotel, the food was good."

The Yankee Inn

10/10 Excellent

"Seamless stay from check in to check out. All the important things like cleanliness and updated bathroom with working faucets, great shower, lots of towels, etc. and unusual amenities like “two” swimming pools as well as hiking (walking) trail and ponds in the rear of the hotel property. Breakfast offerings had a big variety of foods similar to other hotels that offer full breakfast buffets. Located on a business strip with supermarkets and other useful retail stores however the hotel sits back from the road so is fairly quiet especially at night. Our room had a wide covered balcony with Adirondack chairs. Small fire-pit area out in front of the man entrance. Personally, I would have preferred a softer bed but was not uncomfortable and it did not affect my sleep. Linens and pillows were very nice, fluffy, and very clean. No funky hotel odors in the room or halls. The staff was very friendly, polite and helpful. It shows that this facility makes every effort to run a great hotel and please their customers."

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

8/10 Good

"Shower base was very slippery-dangerous. Air-conditioning controls were poor. Thermostat was difficult to adjust and there was no ability to direct the cold air from the fan away from directly blowing on the bed. Had to move furniture to block it. Everything else was fine."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Loved our two-day stay at the Black Swan Inn. We were in the area because we were taking a few programs at the Kripalu Center for one of the days. The room itself was clean, the hall areas could do with better maintenance (which is why I gave that 4 stars) The staff was helpful with any questions. Continental breakfast was decent (though they could do with better coffee). We wished we could have enjoyed the Indian restaurant "Mint" next door, which I hear is really good, but they were closed on Tuesdays, so it was a matter of timing..., but we hope to have a chance next time we are in the area. One of my favorite parts of the property is that it sits by a clean lovely lake, and there are seating areas to enjoy the view anytime of day just to unwind. They also have kayak rentals for those who enjoy the activity. Another wonderful treat- it is near High Lawn Farm, only a 3-min drive from the Inn. It is beautiful there, and cute Jersey cows roam freely, when they are ready they go on their own time into a building where they lay on heated water beds while being milked (I kid you not!). Their dairy products and ice-cream are excellent, worth taking the short drive there. The town center of Lee has some nice restaurants and boutiques within a 5-8 min drive. It was a memorable stay and hope to be back there again soon."

Find out more about South Lee

Everything you need to know about South Lee vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Lee vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Lee vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Lee vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Lee. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit South Lee in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $139 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Lee rentals

At Expedia, we put the best South Lee vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top South Lee rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Lee vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Lee. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Are there vacation rentals in South Lee?

Yes, we have vacation rentals close to popular local attractions in South Lee, or you can go with a more remote option if you'd like a relaxing place to stay. Our travelers say South Lee has a good selection of restaurants and the local cheese shops. Make sure you have time to check out the ski areas and shopping during your trip.

What are some of the best vacation home rentals that South Lee has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental near South Lee is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in South Lee?

Choose from 7 Expedia vacation rentals in South Lee for a memorable vacation.

What’s there to see and do in South Lee?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Housatonic River. Chesterwood and National Shrine of the Divine Mercy are a couple of places you'll find in the larger area.

What’s a vacation rental in South Lee like?

Vacation rentals are private properties you can stay in for a short or long stay in South Lee. Vacation rentals feature extras like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a small group gathering.

Room 1

Check prices for these dates

Our top choices for South Lee vacation rentals

1. Berkshire Mountain Lodge

2. stylish Berkshires Retreat

3. Cozy Riverside Berkshires Retreat

4. Sweet Cozy Victorian in Housatonic. Close to everything.

5. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

6. Stylish Mid-century Modern Berkshires Cape

7. NEW RENO - Chalet-style farm loft near Tanglewood

8. Spacious Central Berkshires Home for Groups

9. Treetop Hideaway in Tyringham

10. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

11. Historic Stockbridge Villa on 25 acres

12. Real Estate: Therapy - Lake, Laundry, Love it

13. Home in Great Barrington

14. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

15. The Brooks Motel: Exceptional Suite

16. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

17. Vacation Village in the Berkshires

18. 1800s Carriage house in Berkshires / Hudson Valley

19. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

20. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Find vacation rentals that suit your style

Top South Lee Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Vacation Village in the Berkshires

The Yankee Inn

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

The Red Lion Inn

Holiday Inn Club Vacations Oak 'n Spruce Resort

Quality Inn Great Barrington

Jiminy Peak Mountain Resort

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about South Lee

Explore a world of travel with Expedia

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