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Holiday Rentals in Weatogue

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Weatogue holiday rentals

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

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (9 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 €137
includes taxes & fees
26 Oct - 27 Oct
Cozy 1-bedroom studio in serene Great Barrington with AC
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

2. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is €389
includes taxes & fees
2 Nov - 3 Nov
Cheerful 3-bedroom cottage with woodstove
A wooden cabin interior with a bench, a rug, and a hanging plant.

3. 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 €181
includes taxes & fees
1 Nov - 2 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

4. 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 €175
includes taxes & fees
21 Oct - 22 Oct
The Brooks Motel: Exceptional Suite
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

5. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (40 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is €321
includes taxes & fees
26 Oct - 27 Oct
Home in Great Barrington
A sandy beach with a lake and forest in the background.

6. 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, (6 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 €282
includes taxes & fees
16 Nov - 17 Nov
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A living room with a fireplace, bookshelves, a television, and a comfortable seating area.

7. 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 €387
includes taxes & fees
21 Oct - 22 Oct
Sharon Retreat w/ Private Yard
A staircase with a wooden handrail and a white wall with a light switch.

8. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is €253
includes taxes & fees
26 Oct - 27 Oct
Leaf-Peeper Paradise in the Berkshires
A compact RV interior with a kitchenette, a sofa with patterned upholstery, and a window with a view.

9. 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 €181
includes taxes & fees
21 Oct - 22 Oct
Cozy Camper tucked into the woods
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

10. 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 €185
includes taxes & fees
21 Oct - 22 Oct
The Brooks Motel: Exceptional Suite
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 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 €313
includes taxes & fees
22 Oct - 23 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

12. 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 €587
includes taxes & fees
21 Oct - 22 Oct
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

13. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 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 €503
includes taxes & fees
16 Nov - 17 Nov
Treetop Hideaway in Tyringham
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

14. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (55 reviews)
"Quiet and peaceful"
United States
Michael S.
The price is €505
includes taxes & fees
23 Oct - 24 Oct
Cozy Cottage-Sunset On The Lake
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is €637
includes taxes & fees
21 Oct - 22 Oct
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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.

16. 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, (9 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 €1,181
includes taxes & fees
22 Oct - 23 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A two-story house with a balcony, a deck, and a view of the surrounding forest.

17. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (134 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
Gorgeous Mountain Views Retreat: Family & Nature
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

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is €586
includes taxes & fees
21 Oct - 22 Oct
Secluded Family Home in Serene Stockbridge 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)
"We loved the house and it really added to our upstate experience!!"
United States
stephen r.
The price is €1,294
includes taxes & fees
28 Oct - 29 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

20. 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 €871
includes taxes & fees
21 Oct - 22 Oct
Chic Barn Style * Fireplace * Near Stissing House
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

Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"Very clean!!! Bathroom was bright. Great value!"
c 1-night trip
Posted 3 hours ago
Monument Mountain Motel

Find out more about Weatogue

Everything you need to know about Weatogue holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Weatogue holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Weatogue holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Weatogue holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Weatogue. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Weatogue holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Weatogue holiday rentals we have selected for you start as low as €137 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Weatogue rentals

At Expedia, we put the best Weatogue holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Weatogue rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Weatogue holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Weatogue. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Weatogue?

Yes, there are holiday rentals close to the most popular sights in Weatogue, 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 Weatogue has to offer?

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: This holiday home rental outside of Weatogue 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 Weatogue?

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

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 wider area.

What are holiday rentals like in Weatogue?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Weatogue. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a small group gathering.