Default HTG hotel image

Weatogue Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Weatogue holiday rentals

Property grounds

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.
The price is HK$1,937
HK$4,064 total
includes taxes & fees
23 Sept - 24 Sept
Cheerful 3-bedroom cottage with woodstove
Coffee/tea maker, fridge, microwave, oven

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.4 out of 10, Exceptional, (3 reviews)
"Great location, great property, great host"
United States
Shelly B.
The price is HK$882
HK$1,292 total
includes taxes & fees
17 Sept - 18 Sept
Cozy 1-bedroom studio in serene Great Barrington with AC
Coffee/tea maker, fridge, microwave, oven

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.
The price is HK$1,496
HK$2,416 total
includes taxes & fees
15 Sept - 16 Sept
Home in Great Barrington
Beach nearby, sun-loungers, beach towels

4. 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.
The price is HK$1,725
HK$2,742 total
includes taxes & fees
16 Sept - 17 Sept
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Terrace/patio

5. 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
The price is HK$1,568
HK$2,977 total
includes taxes & fees
15 Sept - 16 Sept
Ideal location for summer and winter activities with plenty of outdoor space.
Interior

6. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (25 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.
The price is HK$1,588
HK$2,466 total
includes taxes & fees
21 Sept - 22 Sept
Riverside Retreat in the Berkshires
Interior

7. 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.
The price is HK$1,764
HK$2,987 total
includes taxes & fees
4 Oct - 5 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
Interior

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is HK$1,023
HK$1,808 total
includes taxes & fees
14 Sept - 15 Sept
Peaceful and cozy 1 bed 1 bath in quaint Winchester
3 bedrooms, iron/ironing board, WiFi, bed sheets

9. 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.
The price is HK$2,488
HK$4,364 total
includes taxes & fees
15 Sept - 16 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
2 bedrooms, WiFi, bed sheets

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

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
The price is HK$1,722
HK$2,580 total
includes taxes & fees
15 Sept - 16 Sept
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Outdoor dining

11. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
The price is HK$1,503
HK$1,925 total
includes taxes & fees
14 Sept - 15 Sept
Cozy Camper tucked into the woods
TV

12. 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.
The price is HK$2,211
HK$4,525 total
includes taxes & fees
23 Sept - 24 Sept
Treetop Hideaway in Tyringham
Smart TV, books

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

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is HK$3,166
HK$5,311 total
includes taxes & fees
15 Sept - 16 Sept
Fantastic 2-bedroom house with AC in quaint Hillsdale.
TV, fireplace, printers

14. 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.
The price is HK$4,439
HK$10,416 total
includes taxes & fees
13 Sept - 14 Sept
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
TV, fireplace, books

15. 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.
The price is HK$1,441
HK$5,289 total
includes taxes & fees
22 Sept - 23 Sept
NEW: Chic Modern Barn Style Home in Fun Area
Terrace/patio

16. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is HK$3,529
HK$5,322 total
includes taxes & fees
14 Sept - 15 Sept
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Exterior

17. 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, (40 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 traveller
The price is HK$3,607
HK$6,709 total
includes taxes & fees
30 Sept - 1 Oct
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Coffee/tea maker, fridge, microwave, oven

18. 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.
The price is HK$6,979
HK$11,549 total
includes taxes & fees
13 Sept - 14 Sept
A Country Lodge Straight Out of the Pages of a Great Novel
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Weatogue Hotel Reviews

Little Cat Lodge

Little Cat Lodge

10/10 Excellent
"Beautiful and peaceful little lodge with easy access to all the wonderful things in the area (Catamount, Lakes etc..). Pool is very tranquil and each room has Mountain views. The lodge is artfully designed as well, providing a luxury feeling. I only wish 1) the indoor common area was open for guests at any time (but I assume this is a cost/staff issue) 2) there as espessso / coffee/ tea available for guests at a wider ranger of hours (only available at continental breakfast or kureg in room). But these would only be added luxuries and did not materially detract from absolutely delightful stay!!"
Claire 4-night trip
Posted 17 hours ago
Little Cat Lodge

Find out more about Weatogue

Search for holiday rentals in Weatogue on Expedia! You can easily find your home rentals, villas, holiday apartments in Weatogue using one of the methods below:

  • View our selection of featured holiday rentals in Weatogue
  • Use the map to find apartments and other holiday homes in the Weatogue neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Weatogue while they last

Look no further and take a look at our great range of rental properties in Weatogue!

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.