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Weatogue Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$465 nightly
The price is $519
Sep 22 - Sep 23
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
9.0 out of 10, Wonderful, (2 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
$148 nightly
The price is $165
Sep 2 - Sep 3
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

3. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
$364 nightly
The price is $407
Sep 3 - Sep 4
Total with taxes and fees
Home in Great Barrington
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"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.
$483 nightly
The price is $539
Sep 8 - Sep 9
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A modern interior with a loft-style ceiling, a grey sofa, a wooden coffee table, and a kitchen area with a large TV.

5. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
$605 nightly
The price is $677
Aug 27 - Aug 28
Total with taxes and fees
Fantastic 2-bedroom house with AC in quaint Hillsdale.
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, (3 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
$299 nightly
The price is $334
Sep 13 - Sep 14
Total with taxes and fees
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
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.

7. 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, (7 reviews)
"Beautiful house with great amenities in a convenient location. We loved the open concept that provided a great space for cooking, hanging out and playing games together while enjoying a beautiful view. The gameroom was so much fun, and we’d love to visit again when the sauna is finished. Our family of 6 and family dog loved it!"
United States
Rebecca K.
$1,188 nightly
The price is $1,327
Aug 27 - Aug 28
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

8. 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.
$181 nightly
The price is $203
Aug 27 - Aug 28
Total with taxes and fees
The Brooks Motel: Exceptional Suite
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

9. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
$270 nightly
The price is $302
Sep 1 - Sep 2
Total with taxes and fees
Cozy Riverside Berkshires Retreat
A loft bedroom with a television, wooden shelves, a ladder, and a skylight.

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
$198 nightly
The price is $224
Aug 30 - Aug 31
Total with taxes and fees
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

11. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 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.
$551 nightly
The price is $582
Sep 21 - Sep 22
Total with taxes and fees
Treetop Hideaway in Tyringham
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.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 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.
$286 nightly
The price is $319
Sep 1 - Sep 2
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
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

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (15 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
$1,302 nightly
The price is $1,473
Aug 31 - Sep 1
Total with taxes and fees
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.

14. 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
$172 nightly
The price is $193
Aug 30 - Aug 31
Total with taxes and fees
The Brooks Motel: Exceptional Suite
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

15. 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, (51 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
$212 nightly
The price is $240
Sep 1 - Sep 2
Total with taxes and fees
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

16. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (39 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
$846 nightly
The price is $945
Sep 20 - Sep 21
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A two-story house with a covered porch, a front door, and a driveway.

17. Family home by Polo fields with great yard & game rm. EV charger, pet friendly!

Family home by Polo fields with great yard & game rm. EV charger, pet friendly!
Pine Plains
10.0 out of 10, Exceptional, (7 reviews)
"It felt clean, comfortable, accomodating, and most important, safe. Our family had an amazing time here and we will definitely visit again. Thank you!"
United States
Jon W.
Family home by Polo fields with great yard & game rm. EV charger, pet friendly!
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

18. NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
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.
$689 nightly
The price is $778
Sep 22 - Sep 23
Total with taxes and fees
NEW: Chic Modern Barn Style Home in Fun Area
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

19. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
$781 nightly
The price is $872
Sep 2 - Sep 3
Total with taxes and fees
Stylish Mid-century Modern Berkshires Cape

20. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
$309 nightly
The price is $345
Aug 31 - Sep 1
Total with taxes and fees
Quintessential Berkshire Escape - Artist Home, Tucked Away in 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

the Alander

the Alander

10/10 Excellent
"Whenever I'm in Copake, I stay at the Alander!"
Phil 1-night trip
Posted 10 hours ago
the Alander

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 $165 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?

Cozy Riverside Berkshires Retreat: This vacation home near Weatogue is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, 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.