A street lined with historic buildings, including a Morgan House restaurant.

Lee Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Lee holiday rentals

Lobby

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,043 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is HK$982
HK$1,272 total
includes taxes & fees
30 Aug - 31 Aug
Berkshire Mountain Lodge
Smart TV

2. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is HK$1,673
HK$3,542 total
includes taxes & fees
19 Aug - 20 Aug
stylish Berkshires Retreat
4 bedrooms, travel cot, WiFi, bed sheets

3. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is HK$3,988
HK$6,846 total
includes taxes & fees
3 Sept - 4 Sept
Stylish Mid-century Modern Berkshires Cape
Interior

4. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (21 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is HK$1,796
HK$2,733 total
includes taxes & fees
1 Sept - 2 Sept
Cozy Riverside Berkshires Retreat
Outdoor dining

5. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is HK$3,157
HK$4,983 total
includes taxes & fees
30 Aug - 31 Aug
Stockbridge In-town Escape
Smart TV, books

6. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
8.0 out of 10, Very good, (1 review)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is HK$2,541
HK$4,950 total
includes taxes & fees
19 Aug - 20 Aug
Spacious Central Berkshires Home for Groups
Coffee/tea maker, fridge, microwave, oven

7. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (35 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is HK$2,117
HK$3,206 total
includes taxes & fees
12 Aug - 13 Aug
Home in Great Barrington
TV

8. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"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!! "
United States
Samantha G.
The price is HK$2,588
HK$5,024 total
includes taxes & fees
2 Sept - 3 Sept
Treetop Hideaway in Tyringham
Interior

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

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,539
HK$3,436 total
includes taxes & fees
12 Aug - 13 Aug
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is HK$3,427
HK$5,580 total
includes taxes & fees
1 Sept - 2 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Outdoor dining

11. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very good, (9 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is HK$2,463
HK$4,311 total
includes taxes & fees
6 Aug - 7 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Lobby

12. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,503 reviews)
"I have been visiting this property for years and it is always great. Can’t beat it after a few days of adventure in the Berkshires"
United States
Brooks
The price is HK$729
HK$901 total
includes taxes & fees
19 Aug - 20 Aug
Vacation Village in the Berkshires
Exterior

13. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (163 reviews)
"This inn with cabins is a gorgeous setting with a nice vegetable garden, the setting is a bit remote and we like it, very quiet, unfortunately the restaurant was close."
United States
philippe
The price is HK$1,087
HK$1,217 total
includes taxes & fees
10 Aug - 11 Aug
Micosta Leisure Inn
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is HK$2,000
HK$3,303 total
includes taxes & fees
13 Aug - 14 Aug
Sweet Cozy Victorian in Housatonic. Close to everything.
TV, fireplace, printers

15. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is HK$4,030
HK$9,898 total
includes taxes & fees
6 Aug - 7 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Coffee/tea maker, fridge, microwave, oven

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

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (30 reviews)
"Had a fantastic time at Cathy’s place. So clean and everything you need for a great stay. Hope to visit again ! "
United States
Susan M.
The price is HK$1,023
HK$2,545 total
includes taxes & fees
10 Aug - 11 Aug
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Outdoor spa tub

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is HK$1,503
HK$3,396 total
includes taxes & fees
12 Aug - 13 Aug
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Property grounds

18. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (39 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
The price is HK$1,750
HK$3,900 total
includes taxes & fees
6 Aug - 7 Aug
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Room

19. Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (14 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$946
HK$1,056 total
includes taxes & fees
23 Aug - 24 Aug
Huttopia Berkshires
Exterior

20. Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.

Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.
Hinsdale
10.0 out of 10, Exceptional, (9 reviews)
"Kendra was an excellent host! Very nice and welcoming and answered questions promptly. The house was beautiful and the country setting and lake was picturesque. "
United States
Joseph L.
The price is HK$2,314
HK$4,669 total
includes taxes & fees
10 Aug - 11 Aug
Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.
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.
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Top Lee Hotel Reviews

Devonfield Inn B&B

Devonfield Inn B&B

8/10 Good
"The owners are so nice!!! Tha property is beautiful and the people that play the piano and sing during the day is the most relaxing and incredible experience!!!!"
Liliana 2-night trip
Posted 21 hours ago
Devonfield Inn B&B

Find out more about Lee

Search for holiday rentals in Lee on Expedia! You can easily find your home rentals, villas, holiday apartments in Lee using one of the methods below:

  • View our selection of featured holiday rentals in Lee
  • Use the map to find apartments and other holiday homes in the Lee neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Lee while they last

Look no further and take a look at our great range of rental properties in Lee!

Frequently asked questions

Can I find a holiday rental in Lee?

Yes, there are holiday rentals in Lee close to Ashintully Gardens, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and museums in Lee. Leave plenty of time to check out the shops and lakeside during your trip.

What are some of the best holiday rentals that Lee has to offer?

Cozy Riverside Berkshires Retreat: This holiday home rental outside of Lee is located on a river, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and kitchenware, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Lee?

Choose from 44 Expedia holiday rentals in Lee for a memorable holiday.

What can I see and do in Lee?

Cultural attractions include Animagic Museum of Animation and Berkshire Scenic Railway Museum, whereas Goose Pond Reservation and Housatonic River are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Berkshire Mountain Country Store and Lee Premium Outlets.

What are holiday rentals like in Lee?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Lee. Holiday rentals offer amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a family trip.