Weatogue Vacation Rentals from CA $235: Short-Term Rentals for 2026

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Our top choices for Weatogue vacation rentals

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

1. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

CA $607 total

includes taxes & fees

Nov 2 - Nov 3

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

2. Home in Great Barrington

Great Barrington

Janet G.

CA $494 total

includes taxes & fees

Oct 13 - Oct 14

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Great Barrington

Deborah S.

CA $235 total

includes taxes & fees

Oct 30 - Oct 31

A sandy beach with a lake and forest in the background.

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

Great Barrington

Marc R.

CA $470 total

includes taxes & fees

Oct 13 - Oct 14

A wooden cabin with a porch, a grill, and a flower planter.

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

Hillsdale

Richard M.

CA $564 total

includes taxes & fees

Oct 14 - Oct 15

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Great Barrington

Mark M.

CA $1,002 total

includes taxes & fees

Oct 19 - Oct 20

A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

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

winsted

traci

A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

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

Cornwall

Candice S.

CA $856 total

includes taxes & fees

Nov 11 - Nov 12

A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

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

Great Barrington

Roberta

CA $1,890 total

includes taxes & fees

Oct 13 - Oct 14

A staircase with a wooden handrail and a white wall with a light switch.

10. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

CA $402 total

includes taxes & fees

Oct 26 - Oct 27

A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

11. The Brooks Motel: Exceptional Suite

Hillsdale

CA $271 total

includes taxes & fees

Oct 13 - Oct 14

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Housatonic

Peter S.

CA $502 total

includes taxes & fees

Oct 13 - Oct 14

A modern kitchen with white cabinets, a large island, and a skylight.

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

Pine Plains

stephen r.

CA $1,921 total

includes taxes & fees

Oct 16 - Oct 17

A wooden cabin interior with a bench, a rug, and a hanging plant.

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

Winchester

Thomas C.

CA $303 total

includes taxes & fees

Nov 1 - Nov 2

A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

15. Cozy Cottage-Sunset On The Lake

Otis

Michael S.

CA $831 total

includes taxes & fees

Oct 23 - Oct 24

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

16. 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.

CA $808 total

includes taxes & fees

Nov 9 - Nov 10

A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

17. Cozy Camper tucked into the woods

Sandisfield

"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...

hannah w.

CA $287 total

includes taxes & fees

Oct 14 - Oct 15

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

18. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

CA $991 total

includes taxes & fees

Oct 20 - Oct 21

A two-story house with a balcony, a deck, and a view of the surrounding forest.

19. Gorgeous Mountain Views Retreat: Family & Nature

Hillsdale

Anne S.

CA $921 total

includes taxes & fees

Oct 18 - Oct 19

A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

20. Stylish Mid-century Modern Berkshires Cape

Lee

H B.

CA $1,245 total

includes taxes & fees

Oct 18 - Oct 19

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Top Weatogue Hotel Reviews

Little Cat Lodge

10/10 Excellent

"Beyond amazing, we loved it so much!"

The Red Lion Inn

8/10 Good

"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."

Quality Inn Great Barrington

8/10 Good

"First, this is an absolutely gorgeous place! The outside areas are beautiful with comfy furniture, flowers and fire pits. Inside is a small intimate restaurant and bar, plus sitting area. With books and plants, very nice. We had dinner there which was excellent, and loved cocktails and sunset outside by the fire pits. When we checked in, we were assigned one of their premium rooms, which sounded great. However, it was on the second floor, at the very end of a long outside corridor, accessible only by stairs near the lobby. There is no elevator. We did go to the room, lugging our bags and a cooler. Unpleasant, as we are somewhat older. We concluded that we did not want to be that far from the main area, so asked to be moved, and were accommodated. We found the new room the same, but lacking a luggage rack and a coffee service (those were only available in the premium rooms at the end of the long corridor). We were given a luggage rack, and complimentary coffee was available in the restaurant in the morning, but it seemed odd that those were considered premium in such a nice place. Otherwise we loved the hotel, room was very nice with a comfortable bed and a very updated bath with a walk in shower. The real star of the hotel is the lobby restaurant and outdoor space - that was just perfect!"

Find out more about Weatogue

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . Seeing all the best attractions is bound to make you fall in love with Weatogue. Who knows, you may even be tempted to extend your vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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 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. Ashley House 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.

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Check prices for these dates

Our top choices for Weatogue vacation rentals

1. Cheerful 3-bedroom cottage with woodstove

2. Home in Great Barrington

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

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

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

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

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

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

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

10. Leaf-Peeper Paradise in the Berkshires

11. The Brooks Motel: Exceptional Suite

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

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

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

15. Cozy Cottage-Sunset On The Lake

16. Treetop Hideaway in Tyringham

17. Cozy Camper tucked into the woods

18. Secluded Family Home in Serene Stockbridge Woods

19. Gorgeous Mountain Views Retreat: Family & Nature

20. Stylish Mid-century Modern Berkshires Cape

Find vacation rentals that suit your style

Top Weatogue Hotel Reviews

Little Cat Lodge

the Alander

Monument Mountain Motel

The Red Lion Inn

Quality Inn Great Barrington

The Millerton Inn

Holiday Inn Club Vacations Oak 'n Spruce Resort

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Weatogue

Frequently asked questions

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