Weatogue Holiday Rentals from AU$219: Search Short-Term Rentals

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Our top choices for Weatogue holiday rentals

1. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

includes taxes & fees

12 Oct - 13 Oct

Coffee/tea maker, fridge, microwave, oven

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

Great Barrington

Shelly B.

includes taxes & fees

28 Sept - 29 Sept

3. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

21 Sept - 22 Sept

Beach nearby, sun-loungers, beach towels

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

Great Barrington

Kristin O.

includes taxes & fees

20 Sept - 21 Sept

5. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

winsted

paul

includes taxes & fees

28 Sept - 29 Sept

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

Hillsdale

Kenny

includes taxes & fees

20 Sept - 21 Sept

7. Riverside Retreat in the Berkshires

Great Barrington

Kelly B.

includes taxes & fees

20 Sept - 21 Sept

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

Winchester

includes taxes & fees

4 Oct - 5 Oct

9. Cozy Camper tucked into the woods

Sandisfield

includes taxes & fees

23 Sept - 24 Sept

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

Housatonic

Peter S.

includes taxes & fees

25 Sept - 26 Sept

11. Chic Barn Style * Fireplace * Near Stissing House

Pine Plains

Estefany G.

includes taxes & fees

22 Sept - 23 Sept

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

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

Great Barrington

Mary R.

includes taxes & fees

23 Sept - 24 Sept

13. 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

23 Sept - 24 Sept

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

Otis

includes taxes & fees

28 Sept - 29 Sept

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

Hillsdale

includes taxes & fees

20 Sept - 21 Sept

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

Great Barrington

Rebecca K.

includes taxes & fees

21 Sept - 22 Sept

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

Stockbridge

Anonymous traveller

includes taxes & fees

28 Sept - 29 Sept

18. Gorgeous Mountain Views Retreat: Family & Nature

Hillsdale

Anne S.

includes taxes & fees

18 Oct - 19 Oct

19. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Stanfordville

includes taxes & fees

23 Sept - 24 Sept

4 bedrooms, travel cot, WiFi, bed sheets

20. Stylish Mid-century Modern Berkshires Cape

Lee

H B.

includes taxes & fees

18 Oct - 19 Oct

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Top Weatogue Hotel Reviews

the Alander

8/10 Good

"Lots of good to great here but there still are some things that need attention. This is an old school motel being updated that has a lovely restaurant. The rooms that have been renovated are charming and comfortable but property still has more rooms being renovated. Lots of attention to detail to make your stay comfortable from thoughtful local map, homemade granola from their restaurant with local yogurt to enjoy for breakfast with french press coffee or tea. Nicely stocked items in the room's minibar. Comfortable bed, good sized closet. Also had dinner here with a family member who lives nearby. Lovely meadow at the property. Nice sized fire pits. Charming - but, I feel that a lot of details were overlooked. The bathroom in my room needs attention. The tile is older tile that has been painted and I get that this is a cost saving measure but combined with newer dark fixtures and dark toilet seat that had a worn finishes and a good number of hairs and dirt in the bath and shower I think the cleaning staff needs to be taught to have better eyes for details. A door that I thought might hold additional closet space or perhaps a desk but instead it had a pile of old air conditioners and the door and doorway were scraped up. Seems like this should have been locked. The room was good sized but could use a desk so there was a place to work. Couldn't use the fire pits as there wasn't any wood. Staff was responsive via text and helpful. I would consider coming back."

The Red Lion Inn

8/10 Good

"Bedding and bed were lovely. excellent to have good lighting at sink as well as a magnified mirror! Often lacking in places we have stayed. AC had trouble cooling the room down until we turned it on full blast. too much ambient light from floodlight on property next door and from hall (I finally turned off hallway light which helped. ) Common areas and halls need some brightening up with fresh, lighter paint--seemed dingy. Was terribly frustrating trying to make the Nespresso machine work. We do not own one and there were NO INSTRUCTIONS. You should assume people do not know how to operate any appliances like that and should have a card with directions. We gave up and went to the Tavern where we had lovely coffee and breakfast. Also had a great dinner in Tavern after our arrival. The patch burrata salad was superb. As was our waitress."

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 favourite 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 depend 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 AU$219 per night. Entering your travel dates in the search wizard might find you 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. 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. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

5. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

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

7. Riverside Retreat in the Berkshires

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

9. Cozy Camper tucked into the woods

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

11. Chic Barn Style * Fireplace * Near Stissing House

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

13. Treetop Hideaway in Tyringham

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

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

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

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

18. Gorgeous Mountain Views Retreat: Family & Nature

19. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

20. Stylish Mid-century Modern Berkshires Cape

Find holiday rentals that suit your style

Top Weatogue Hotel Reviews

the Alander

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Little Cat Lodge

The Red Lion Inn

Locust Tree Bed and Breakfast LLC

Quality Inn Great Barrington

Monument Mountain Motel

Find out more about Weatogue

Frequently asked questions

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