Weatogue Vacation Rentals

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Check prices for these dates

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Weatogue vacation rentals

Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

Vacation Home in Goshen

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is ￥13,817
￥96,917 total
includes taxes & fees
Jan 4 - Jan 5, 2026
CT Gate House Goshen CT, Gate House Goshen CT
Property grounds
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Apartment in winsted

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
9.2 out of 10, Wonderful, (46)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is ￥13,910
￥26,301 total
includes taxes & fees
Dec 30 - Dec 31
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Dining
Guesthouse Cabin vacation rentals in Berkshire County

Cabin in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is ￥61,355
￥105,329 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Guesthouse Cabin vacation rentals in Berkshire County
Outdoor dining
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Vacation Home in Hillsdale

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
10.0 out of 10, Exceptional, (1)
"Beautiful house! It was a big house and we loved all the rooms and how they were decorated! When we first arrived the heat wasn’t working and the host had someone there with the half hour fixing the problem. Beautiful quite area as well "
United States
Gabrielle T.
The price is ￥60,887
￥175,204 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Exterior detail
Whispering Estate Guest House - A Romantic Countryside Getaway

Vacation Home in Goshen

Whispering Estate Guest House - A Romantic Countryside Getaway
10.0 out of 10, Exceptional, (5)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is ￥124,896
￥187,890 total
includes taxes & fees
Dec 25 - Dec 26
Whispering Estate Guest House - A Romantic Countryside Getaway
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Vacation Home in Great Barrington

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (3)
"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 ￥88,801
￥208,008 total
includes taxes & fees
Dec 25 - Dec 26
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
The price is ￥23,605
￥40,143 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Home in Great Barrington
Exterior
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Vacation Home in Goshen

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
2.0 star property
The price is ￥41,372
￥82,822 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
TV, offices
The Brooks Motel: Exceptional Suite

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
7.0 out of 10, Good, (4)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
The price is ￥24,823
￥31,299 total
includes taxes & fees
Dec 27 - Dec 28
The Brooks Motel: Exceptional Suite
Property grounds
Cheerful 3-bedroom cottage with woodstove

Vacation Home in Sheffield

Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥37,000
￥78,298 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Cheerful 3-bedroom cottage with woodstove
Game room
Family Ski Getaway in the Berkshires

Vacation Home in Great Barrington

Family Ski Getaway in the Berkshires
9.4 out of 10, Exceptional, (6)
The price is ￥31,614
￥46,474 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Family Ski Getaway in the Berkshires
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Vacation Home in Great Barrington

Cozy. Clean. Free bagel shop. 3 Fireplaces.
10.0 out of 10, Exceptional, (1)
"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 ￥53,081
￥91,727 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Fridge, microwave, oven, stovetop
Catamount, Zip Line, Private Setting, Book Now!

Vacation Home in Egremont

Catamount, Zip Line, Private Setting, Book Now!
10.0 out of 10, Exceptional, (7)
"This was a very lovely home to stay in for our family, everything you need is in the house (basic things minus food of course) We would definitely book this house again when we visit the Berkshires again."
United States
Jason W.
The price is ￥101,985
￥217,228 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Catamount, Zip Line, Private Setting, Book Now!
Fridge, microwave, oven, stovetop
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Vacation Home in Monterey

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
10.0 out of 10, Exceptional, (1)
"Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."
United States
Kim H.
The price is ￥132,390
￥276,796 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Vacation Home in Great Barrington

Great Barrington Get Away
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is ￥48,397
￥85,799 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Great Barrington Get Away
Fridge, microwave, oven, stovetop
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Apartment in Great Barrington

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
The price is ￥61,964
￥77,932 total
includes taxes & fees
Dec 28 - Dec 29
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
TV, offices
The Brooks Motel: Exceptional Suite

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is ￥24,823
￥31,649 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Brooks Motel: Exceptional Suite
Fridge, microwave, stovetop, coffee/tea maker
Brooks Motel: Perfect Suite, Seasonal Waterviews

Apartment in Hillsdale

Brooks Motel: Perfect Suite, Seasonal Waterviews
6.0 out of 10, (1)
"NO HOT WATER!!! My room had exposed wood not like the photo. Musty smell in living room."
United States
Joan V.
The price is ￥22,481
￥28,676 total
includes taxes & fees
Dec 25 - Dec 26
Brooks Motel: Perfect Suite, Seasonal Waterviews
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 Weatogue Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"The staff is always so helpful & nice, and the rooms are always clean and comfortable. This is my favorite place to stay in Lee!"
Cooper 1-night trip
Posted 4 days ago
Quality Inn

Find out more about Weatogue

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

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

Frequently asked questions

Can I find a vacation rental in Weatogue?

Yes, you can find vacation rentals near top local attractions in Weatogue, or you can select a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Weatogue has to offer?

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: This vacation home rental near Weatogue offers a fireplace, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Weatogue?

Choose from 3 Expedia vacation rentals in Weatogue for a memorable vacation.

What can I see and do in Weatogue?

Explore the area and family-friendly sights such as Harney and Sons Tea Tasting Room, or get out into nature at a spot like Housatonic River. Mount Riga State Park and Great Falls are a couple of places you'll find in the larger area.

What are vacation rentals like in Weatogue?

Vacation rentals are private accommodations you can book for a short or long stay in Weatogue. Vacation rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for families.