Weatogue Holiday Rentals from NZ$280: Search Short-Term Rentals

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

The Meadows House @ Otis Ridge w/ 7-person hot tub : This holiday home rental outside of Weatogue is located in the mountains, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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Our top choices for Weatogue holiday rentals

1. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

includes taxes & fees

22 Sept - 23 Sept

Coffee/tea maker, fridge, microwave, oven

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

Great Barrington

"Michael’s place in Great Barrington MA was incredible. It was clean, very well appointed, affordable and so quiet. It is also very close to numerous restaurant options and grocery stores. I thought the place was very cozy and so comfortable. This was a stopping off point for me so I unfortunately was not able to stay longer. Next time I am Great Barrington I will definitely look up Michael’s place. Thank you Michael."

Paul J.

includes taxes & fees

9 Sept - 10 Sept

3. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

6 Sept - 7 Sept

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

Hillsdale

Kenny

includes taxes & fees

7 Sept - 8 Sept

Beach nearby, sun-loungers, beach towels

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

Great Barrington

Kristin O.

includes taxes & fees

14 Sept - 15 Sept

6. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

includes taxes & fees

8 Sept - 9 Sept

Desk, iron/ironing board, WiFi, bed sheets

7. The Brooks Motel: Exceptional Suite

Hillsdale

Joan

includes taxes & fees

16 Sept - 17 Sept

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

Housatonic

Peter S.

includes taxes & fees

9 Sept - 10 Sept

3 bedrooms, iron/ironing board, WiFi, bed sheets

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

Great Barrington

Mary R.

includes taxes & fees

14 Sept - 15 Sept

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

Winchester

includes taxes & fees

13 Sept - 14 Sept

11. Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale

Annetta D.

includes taxes & fees

13 Sept - 14 Sept

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.

includes taxes & fees

21 Sept - 22 Sept

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

Hillsdale

includes taxes & fees

6 Sept - 7 Sept

14. Cozy Camper tucked into the woods

Sandisfield

includes taxes & fees

14 Sept - 15 Sept

15. The Brooks Motel: Exceptional Suite

Hillsdale

Deidre H.

includes taxes & fees

16 Sept - 17 Sept

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

Otis

includes taxes & fees

7 Sept - 8 Sept

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

Great Barrington

Rebecca K.

includes taxes & fees

7 Sept - 8 Sept

18. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Stanfordville

includes taxes & fees

4 Sept - 5 Sept

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

Pine Plains

Estefany G.

includes taxes & fees

15 Sept - 16 Sept

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

Stockbridge

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Top Weatogue Hotel Reviews

The Little Lion

10/10 Excellent

"Easy check in. The rooms were clean. Beds comfy."

Blackberry River Inn

8/10 Good

"Historic Inn with great full breakfast. Plenty of parking. Lovely old property. The couple running it were very nice and helpful and the breakfast was fantastic. I took off a star because the property needs some TLC. No central air (window units) our bathroom door kept kept sticking, etc. Just generally doesn't seem like it has had any major work in a decades or two."

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 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, 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 NZ$280 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?

The Meadows House @ Otis Ridge w/ 7-person hot tub: This holiday home rental outside of Weatogue is located in the mountains, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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. Mount Riga State Park 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.

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Check prices for these dates

Our top choices for Weatogue holiday 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 holiday rentals that suit your style

Top Weatogue Hotel Reviews

The Little Lion

Blackberry River Inn

Quality Inn Great Barrington

The Red Lion Inn

Monument Mountain Motel

Locust Tree Bed and Breakfast LLC

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Sunset Inn

the Alander

Find out more about Weatogue

Frequently asked questions

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