Weatogue Vacation Rentals from $165: Search Short-Term Rentals

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

The Meadows House @ Otis Ridge w/ 7-person hot tub : This vacation home near Weatogue is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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Our top choices for Weatogue vacation rentals

1. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

$461 nightly

Sep 22 - Sep 23

Total with taxes and fees

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

Great Barrington

Shelly B.

$148 nightly

Sep 10 - Sep 11

Total with taxes and fees

3. Home in Great Barrington

Great Barrington

HEATHER G.

$330 nightly

Sep 8 - Sep 9

Total with taxes and fees

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

Hillsdale

Kenny

$339 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Great Barrington

Kristin O.

$283 nightly

Sep 14 - Sep 15

Total with taxes and fees

6. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

$270 nightly

Sep 15 - Sep 16

Total with taxes and fees

7. The Brooks Motel: Exceptional Suite

Hillsdale

Joan

$170 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Housatonic

Peter S.

$286 nightly

Sep 9 - Sep 10

Total with taxes and fees

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

Great Barrington

Mary R.

$496 nightly

Sep 14 - Sep 15

Total with taxes and fees

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

Winchester

$197 nightly

Sep 13 - Sep 14

Total with taxes and fees

11. Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale

Annetta D.

$471 nightly

Sep 13 - Sep 14

Total with taxes and fees

12. 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.

$546 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Hillsdale

$605 nightly

Sep 6 - Sep 7

Total with taxes and fees

14. Cozy Camper tucked into the woods

Sandisfield

$227 nightly

Sep 14 - Sep 15

Total with taxes and fees

15. The Brooks Motel: Exceptional Suite

Hillsdale

Deidre H.

$179 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Otis

$309 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Great Barrington

Rebecca K.

$1,189 nightly

Sep 6 - Sep 7

Total with taxes and fees

18. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Stanfordville

$609 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Pine Plains

Estefany G.

$620 nightly

Sep 22 - Sep 23

Total with taxes and fees

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

Stockbridge

Anonymous traveler

$766 nightly

Sep 28 - Sep 29

Total with taxes and fees

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Top Weatogue Hotel Reviews

Blackberry River Inn

10/10 Excellent

"Great, quaint country inn. Felt like you were staying a nice, old house. Lovely breakfast. Very convenient to Salisbury School. Nice part of CT and not far from the airport. Will definitely stay there again. Thank you!"

Quality Inn Great Barrington

10/10 Excellent

"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."

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.

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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?

The Meadows House @ Otis Ridge w/ 7-person hot tub: This vacation home near Weatogue is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.

Weatogue Vacation Rentals

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Check prices for these dates

Our top choices for Weatogue vacation rentals

1. Cheerful 3-bedroom cottage with woodstove

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

3. Home in Great Barrington

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

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

6. Cozy Riverside Berkshires Retreat

7. The Brooks Motel: Exceptional Suite

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

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

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

11. Perfect House In Hillsdale, Brings Friends & Fam

12. Treetop Hideaway in Tyringham

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

14. Cozy Camper tucked into the woods

15. The Brooks Motel: Exceptional Suite

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

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

18. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

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

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

Find vacation rentals that suit your style

Top Weatogue Hotel Reviews

Blackberry River Inn

Find out more about Weatogue

Explore a world of travel with Expedia

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