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Weatogue Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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

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.
$382 nightly
The price is $427
Nov 2 - Nov 3
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

2. 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, (8 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.
$125 nightly
The price is $140
Oct 18 - Oct 19
Total with taxes and fees
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.

3. 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)
"Clean property, very cute. Also very small. Cable/tv access was challenging, but all on all a good experience"
United States
traci
$210 nightly
The price is $238
Oct 12 - Oct 13
Total with taxes and fees
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
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
$170 nightly
The price is $190
Oct 11 - Oct 12
Total with taxes and fees
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, (39 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
$311 nightly
The price is $348
Oct 13 - Oct 14
Total with taxes and fees
Home in Great Barrington
A wooden cabin interior with a bench, a rug, and a hanging plant.

6. 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, (2 reviews)
"Great place and wonderful host."
United States
Thomas C.
$186 nightly
The price is $211
Nov 1 - Nov 2
Total with taxes and fees
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A sandy beach with a lake and forest in the background.

7. 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)
"Amazing apartment! Clean, large, close walk to downtown Great Barrington. Joseph was an incredible host - accurate description, great communication. Will definitely be back!"
United States
Marc R.
$294 nightly
The price is $328
Oct 12 - Oct 13
Total with taxes and fees
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
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, (28 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.
$275 nightly
The price is $307
Oct 26 - Oct 27
Total with taxes and fees
Leaf-Peeper Paradise in the Berkshires
A wooden cabin with a porch, a grill, and a flower planter.

9. 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, (79 reviews)
"Excellent host!"
United States
Kenny
$350 nightly
The price is $392
Oct 12 - Oct 13
Total with taxes and fees
Ideal location for summer and winter activities with plenty of outdoor space.
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

10. 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.
$314 nightly
The price is $351
Oct 13 - Oct 14
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
A fireplace with a TV above it, a Christmas tree with red ornaments, and a red bow.

11. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (54 reviews)
"Quiet and peaceful"
United States
Michael S.
$505 nightly
The price is $564
Oct 23 - Oct 24
Total with taxes and fees
Cozy Cottage-Sunset On The Lake
A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

12. 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.
$180 nightly
The price is $201
Nov 2 - Nov 3
Total with taxes and fees
Cozy Camper tucked into the woods
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

13. 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.
$178 nightly
The price is $199
Oct 11 - Oct 12
Total with taxes and fees
The Brooks Motel: Exceptional Suite
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

14. 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.
$534 nightly
The price is $564
Nov 9 - Nov 10
Total with taxes and fees
Treetop Hideaway in Tyringham
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, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
$622 nightly
The price is $695
Oct 19 - Oct 20
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

16. 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.
$513 nightly
The price is $583
Nov 10 - Nov 11
Total with taxes and fees
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A two-story house with a front porch, surrounded by lush greenery and trees.

17. Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam
Hillsdale
8.4 out of 10, Very good, (5 reviews)
"Overall a very pleasant stay. It is a cool old house with all its charm and quirks. Very spacious, comfortable. Decent kitchen. Location very accessible for mountains and tooling around. Just right for a getaway"
United States
Annetta D.
$634 nightly
The price is $710
Oct 11 - Oct 12
Total with taxes and fees
Perfect House In Hillsdale, Brings Friends & Fam
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

18. 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.
$672 nightly
The price is $760
Oct 29 - Oct 30
Total with taxes and fees
Chic Barn Style * Fireplace * Near Stissing House
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.

19. 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
$1,189 nightly
The price is $1,328
Oct 12 - Oct 13
Total with taxes and fees
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.

20. 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.
$575 nightly
The price is $643
Oct 18 - Oct 19
Total with taxes and fees
Gorgeous Mountain Views Retreat: Family & Nature
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

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good
"no comment"
Thomas 1-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak 'n Spruce Resort

Find out more about Weatogue

Everything you need to know about Weatogue vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Weatogue vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Weatogue vacation 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 low season months. For more hustle and bustle, you may prefer to visit Weatogue in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $140 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Weatogue rentals

At Expedia, we put the best Weatogue vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.