Falls Village Historic District Holiday Rentals

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Holiday Rentals in Falls Village Historic District

The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Interior

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.8 out of 10, Exceptional, (37)
"Beautiful property located in the woods with plenty of privacy. 3 floors with a lot of elbow room and a tennis court also! Very good communication with the owners with easy check in/check out instructions. "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Spectacular Short Term Vacation Rental in Kent
Exterior

Spectacular Short Term Vacation Rental in Kent

9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Fridge, microwave, oven, stovetop

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

10.0 out of 10, Exceptional, (90)
"Very clean, spacious, and comfortable. Property manager’s information was helpful."
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Idillic summer getaway in Litchfield Hills, CT.
Exterior

Idillic summer getaway in Litchfield Hills, CT.

10.0 out of 10, Exceptional, (13)
"The place was as described and very comfortable. We enjoyed our stay!"
Idillic summer getaway in Litchfield Hills, CT.
Private Estate, Heated YEARROUND Outdoor Pool
Fridge, microwave, oven, stovetop

Private Estate, Heated YEARROUND Outdoor Pool

10.0 out of 10, Exceptional, (13)
"The country setting provided a quiet retreat. The home is well equipped: plenty of beds, multiple gathering places, pool with towels (although it was pretty cold until the pool guy came and provided help). The outdoor grill provides additional cooking space. The home is within easy driving to many places of interest. We had a nice week at this home."
Private Estate, Heated YEARROUND Outdoor Pool
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Smart TV, fireplace, ping pong, stereo

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

9.8 out of 10, Exceptional, (19)
"Gorgeous home and property, loved being on the lake with the game room cabana, the outdoor areas are so relaxing, and the home is so tastefully decorated. We enjoyed it so much!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (18)
"Very nice, as expected! "
The price is AU$577
includes taxes & fees
26 Nov - 27 Nov
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Great Barrington Walkable to Lake and Town!
Fridge, microwave, oven, stovetop

Great Barrington Walkable to Lake and Town!

9.6 out of 10, Exceptional, (5)
"Needed a rental in a hurry, lucked into Lucas’ house. Quiet, comfortable and cozy. Great visit. Thank you for hosting me and Birdie. "
Great Barrington Walkable to Lake and Town!
Cottage at Copake Lake
Property grounds

Cottage at Copake Lake

10.0 out of 10, Exceptional, (61)
"House was very clean and cozy. Has everything you need and we were very comfortable. Really peaceful location. Short walk to dock where they have paddle board, kayak and seating. Highly recommend if you’re looking for a place at Cooke lake."
Cottage at Copake Lake
Perfect Vacation Get Away - Historical New Marlborough
Property grounds

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (54)
"It was a pleasure to find this gem of a cabin available for a night so we could attend a concert at Tanglewood, despite living out of state. The location was lovely, convenient and quiet; the cabin was impeccably appointed (thanks for the fresh flowers in every room and bottle of Riesling!) and very clean with every possible amenity; and the hosts were communicative, friendly and helpful. Overall, this was an idyllic mix of quaint/cute/unique and function/comfort/ease. I will absolutely seek out...
Perfect Vacation Get Away - Historical New Marlborough
Peaceful, Post and Beam Loft, Sleeps 9
1 bedroom, iron/ironing board, WiFi, bed sheets

Peaceful, Post and Beam Loft, Sleeps 9

10.0 out of 10, Exceptional, (14)
"House and grounds are large! Firepit is great! Local hiking and restaurants were fantastic! Enjoyed the large rooms and decor and artworks and prints."
Peaceful, Post and Beam Loft, Sleeps 9
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (30)
"Delightful home in very quiet neighborhood near hiking trails. House had every amenity you might need (except tissues). Less than 20 minutes drive from Sheffield. Great restaurants in town. We very much enjoyed our stay in this house in the country and would highly recommend it to anyone wanting to stay in the area."
The price is AU$789
includes taxes & fees
26 Nov - 27 Nov
Cheerful 3-bedroom cottage with woodstove
Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
7 bedrooms, free WiFi, bed sheets

Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington

10.0 out of 10, Exceptional, (25)
"It was a quirky and interesting house!"
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
Romantic and Secluded Berkshire's Gem
Fridge, microwave, oven, stovetop

Romantic and Secluded Berkshire's Gem

9.8 out of 10, Exceptional, (11)
"We enjoyed our 2 week stay at this cute rustic cabin. The owner and caretakers were super responsive to our needs during our stay. The only thing that was missing was onsite laundry, but the laundromat was nearby so not a huge inconvenience. Overall, great place to relax in the woods."
Romantic and Secluded Berkshire's Gem
Great Barrington Get Away
Fridge, microwave, oven, stovetop

Great Barrington Get Away

9.2 out of 10, Wonderful, (22)
"Well-located home, comfortable home with a well-stocked kitchen and plenty of space. We hope to return! "
The price is AU$790
includes taxes & fees
26 Nov - 27 Nov
Great Barrington Get Away
'The Mill River Cabin’ w/ Fireplace & River View!
TV, streaming services

'The Mill River Cabin’ w/ Fireplace & River View!

9.8 out of 10, Exceptional, (37)
"The Mill River Cabin is the perfect location for a vacation focused on relaxation and communing with nature! We recently enjoyed a beautiful fall week at this property. Highlights included time spent on the deck overlooking the Konkapot River, evening campfires, hiking the large number/variety of trails very nearby, Hancock Shaker Village and the Norman Rockwell Museum. This rustic cabin has everything you need to make for an enjoyable stay. It's a good idea to bring your food and other...
'The Mill River Cabin’ w/ Fireplace & River View!
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Property grounds

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

9.2 out of 10, Wonderful, (37)
"We loved the brilliant use of space and all the amenities in this cozy hideaway. My husband, who owns a Professional Organization business, was very pleased and impressed by the clever use of various storage options. The walkways were attractively and effectively lit up for evening strolls and dog walking. All instructions were clearly communicated and our stay was lovely"
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated
Fridge, microwave, oven, stovetop

Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated

9.8 out of 10, Exceptional, (9)
"We loved our stay! Andrea responded to questions very quickly. The house was very clean and had everything we needed. We appreciated the treat that was left on the island. We were there only 2 nights and wish we stayed longer. We would definitely stay again. "
Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated
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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Other types of properties in Falls Village Historic District you may be interested in

Quality Inn
Standard Room, 2 Queen Beds, Non Smoking

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1054)
"The young man who worked the Saturday evening shift until 11 ,was a true gentleman "
The price is AU$122
includes taxes & fees
9 Dec - 10 Dec
Quality Inn
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Standard Room

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

2.5 star property
8.8 out of 10, Excellent, (564)
"Look clean, great staffs."
The price is AU$203
includes taxes & fees
3 Dec - 4 Dec
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Reception

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.2 out of 10, Wonderful, (672)
"Great hotel with nice staff and facilities. Close to grocery, restaurants and Stockbridge tourist attractions."
The price is AU$261
includes taxes & fees
1 Dec - 2 Dec
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Frequently asked questions

Can I find a holiday rental in Falls Village Historic District?

Yes, there are holiday rentals close to the most popular sights in Falls Village Historic District, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Falls Village Historic District has to offer?

Cheerful 3-bedroom cottage with woodstove: This holiday home rental outside of Falls Village Historic District is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a private garden and a selection of games.

What’s there to see and do in Falls Village Historic District?

Explore the area and family-friendly sights such as Harney and Sons Tea Tasting Room, or get out into nature at a spot like Mount Frissell. Lime Rock Park and Music Mountain are a couple of places you'll find in the wider area.

What’s a holiday rental in Falls Village Historic District like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Falls Village Historic District. Holiday rentals offer extras like WiFi and washers and dryers so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a family trip.