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Falls Village Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Falls Village holiday rentals

A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

1. Sharon Retreat w/ Private Yard

Sharon Retreat w/ Private Yard
Sharon
9.2 out of 10, Wonderful, (37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
The price is NZ$797
includes taxes & fees
2 Nov - 3 Nov
Sharon Retreat w/ Private Yard
A wooden cabin interior with a bench, a rug, and a hanging plant.

2. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is NZ$335
includes taxes & fees
8 Nov - 9 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

3. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is NZ$205
includes taxes & fees
8 Nov - 9 Nov
Cozy 1-bedroom studio in serene Great Barrington with AC
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

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

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (55 reviews)
"It was a nice stay…worked well for the event we attended in town. The host was very nice to work with"
United States
Roberta S.
The price is NZ$361
includes taxes & fees
3 Nov - 4 Nov
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

5. Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (6 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is NZ$1,021
includes taxes & fees
11 Nov - 12 Nov
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A living room with a fireplace, two armchairs, a sofa, and a TV.

6. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
The price is NZ$314
includes taxes & fees
2 Nov - 3 Nov
Mid Century Modern Studio w/ Full Kitchen - Newly Built
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

7. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is NZ$709
includes taxes & fees
2 Nov - 3 Nov
Cheerful 3-bedroom cottage with woodstove
A wooden nightstand with a lamp, a bowl, and a power outlet on the wall.

8. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.6 out of 10, Exceptional, (7 reviews)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is NZ$630
includes taxes & fees
2 Nov - 3 Nov
Cozy Attic 10 min to Llitchfield
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

9. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is NZ$376
includes taxes & fees
2 Nov - 3 Nov
The Brooks Motel: Exceptional Suite
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

10. Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is NZ$752
includes taxes & fees
2 Nov - 3 Nov
Art House 3 Beds Close to Warner Theater
A two-story house with a front porch, a small balcony, and a white picket fence.

11. Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is NZ$723
includes taxes & fees
1 Dec - 2 Dec
Cozy Modern Farmhouse Private Apt - 3 Beds
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

12. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (41 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is NZ$561
includes taxes & fees
9 Nov - 10 Nov
Home in Great Barrington
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

13. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (22 reviews)
"It was great!"
United States
Amanda T.
The price is NZ$494
includes taxes & fees
2 Nov - 3 Nov
Pristine Cozy Walkable Downtown 2BR Getaway
A sandy beach with a lake and forest in the background.

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

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is NZ$571
includes taxes & fees
3 Nov - 4 Nov
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A wooden cabin with a porch, a grill, and a flower planter.

15. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (80 reviews)
"We very much enjoyed our two week stay in July. The cabin suited our needs in every regard. Our lab was also able to fully relax, whether it was napping on the screen porch or sitting by the fire pit. For those looking to explore the region, the location could not be better situated. Hoping to return over Christmas."
United States
Richard M.
The price is NZ$674
includes taxes & fees
2 Nov - 3 Nov
Ideal location for summer and winter activities with plenty of outdoor space.
A modern kitchen with a wooden dining table, blue chairs, and a decorative bowl centerpiece.

16. Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is NZ$1,010
includes taxes & fees
2 Nov - 3 Nov
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

17. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is NZ$1,129
includes taxes & fees
3 Nov - 4 Nov
Chic Barn Style * Fireplace * Near Stissing House
A wooden fence, a potted plant, a wooden bench, and a small garden area with a stone pathway.

18. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
United States
hannah w.
The price is NZ$309
includes taxes & fees
7 Nov - 8 Nov
Cozy Camper tucked into the woods
A modern kitchen with white cabinets, a large island, and a skylight.

19. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (15 reviews)
"Stayed with a group for Millbrook Horse Trials, we had an amazing weekend at this calm and relaxing home with plenty of beds and amenities! What a treat!"
United States
Marianne R.
The price is NZ$2,433
includes taxes & fees
3 Nov - 4 Nov
A Country Lodge Straight Out of the Pages of a Great Novel
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

20. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very good, (8 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is NZ$376
includes taxes & fees
2 Nov - 3 Nov
The Brooks Motel: Exceptional Suite
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 Falls Village Hotel Reviews

Prospect Berkshires

Prospect Berkshires

10/10 Excellent
"Great experience!"
Sunny 3-night trip
Posted 23 hours ago
Prospect Berkshires

Find out more about Falls Village

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Falls Village holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Falls Village. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Falls Village. Seeing all the best attractions is bound to make you fall in love with Falls Village. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Falls Village short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Falls Village?

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

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

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: This holiday home rental outside of Falls Village offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, 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 Falls Village?

Expedia has 3 holiday rentals for your stay in Falls Village.

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

Great Falls and Housatonic River are a couple of scenic spots to enjoy the outdoors, whereas Music Mountain is one of the cultural attractions. In the wider area, you’ll find Great Mountain Forest and Lime Rock Park.

What’s a holiday rental in Falls Village like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Falls Village. Holiday rentals feature extras such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for family trips.