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Top Holiday Rentals in Weatogue

The Freeman - Newly Renovated 14K SF Estate on 40 Acres
7 bedrooms, iron/ironing board, cots/infant beds, travel cot
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (28)
"We've stayed in a lot of home rentals - and across the board - this was the best place ever. The home was clean, nicely decorated and super comfortable. The hosts were easy to get a hold of and incredibly welcoming, leaving us with a generous basket of local treats. We loved the peaceful outdoor space and roamed all 40 acres. The pond was beautiful and if it had only been warmer we'd have jumped in the rowboat. We will be back for sure. A++ Thank you, Anna!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Interior
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Stockbridge Home, Come Experience The Berkshires!
Fridge, microwave, oven, stovetop
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (10)
"The hosts have made this ranch house into an artsy, cozy place for families to rest and relax! Plenty of space for family hang outs and game playing, but also enough rooms for tweens or teens to get away and have alone time. Beautiful spaces throughout. We would have loved to enjoy the backyard space and screened-in porch if it hadn't been winter, but appreciated watching the snow falling while sipping coffee by the kitchen window! Close to Catamount ski area and minutes from Stockbridge shops...
Stockbridge Home, Come Experience The Berkshires!
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Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Fridge, microwave, oven, stovetop
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Serene Acreage - Pond - Hiking Trails Nearby
Property grounds
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (4)
"Perfect place to relax and have dogs as part of a mini vacation. Very clean, organized, and provided helpful local information. Will definitely stay there again."
Serene Acreage - Pond - Hiking Trails Nearby
Private Island - On Largest Fresh Water Reservoir in Mass. 24' Pontoon boat
Property grounds
Private Island - On Largest Fresh Water Reservoir in Mass. 24' Pontoon boat
10.0 out of 10, Exceptional, (3)
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - On Largest Fresh Water Reservoir in Mass. 24' Pontoon boat
Newly Renovated Family House On Highland Lake with Dock
Fridge, microwave, oven, stovetop
Newly Renovated Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (17)
"The property was perfect for our needs. Instructions for everything was provided fabulous rental. "
Newly Renovated Family House On Highland Lake with Dock
Romantic and Secluded Berkshire's Gem
Fridge, microwave, oven, stovetop
Romantic and Secluded Berkshire's Gem
10.0 out of 10, Exceptional, (9)
"My friends and I had an amazing time staying in the cozy cabin. 9 of us slept comfortably, the place was spotless, and so cute. We hope to visit again."
Romantic and Secluded Berkshire's Gem
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Moose Lodge by AvantStay | Luxe Berkshires Escape
Outdoor dining
Moose Lodge by AvantStay | Luxe Berkshires Escape
9.8 out of 10, Exceptional, (10)
"It was unique, with unusual amenities, like the home theater and fabulous game room. Our weather was wintery, so this was such a comfortable and fun way for the family to spend time together!"
Moose Lodge by AvantStay | Luxe Berkshires Escape
Cozy Cabin in the Berkshires
Property grounds
Cozy Cabin in the Berkshires
10.0 out of 10, Exceptional, (3)
"Cant wait to book again. Great place for familys. Owner thinks of everything that you would need during your stay."
Cozy Cabin in the Berkshires
Rockspring by AvantStay | Huge Berkshires Estate
Interior
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"
Rockspring by AvantStay | Huge Berkshires Estate
Berkshires Cabin 2 Mi to Appalachian Trail!
Interior
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
Perfect Vacation Get Away - Historical New Marlborough
Property grounds
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is £215
includes taxes & fees
8 May - 9 May
Perfect Vacation Get Away - Historical New Marlborough
Remodeled Lakefront retreat w/firepit, close to skiing, golf, and hiking trails!
Aerial view
Remodeled Lakefront retreat w/firepit, close to skiing, golf, and hiking trails!
Remodeled Lakefront retreat w/firepit, close to skiing, golf, and hiking trails!
The Goshen Glass Chalet
Outdoor dining
The Goshen Glass Chalet
9.4 out of 10, Exceptional, (21)
"We came up to celebrate a family Birthday, great place to stay, The host has tons of little extras that are really great. Thank you for a great stay."
The Goshen Glass Chalet
Beautiful retreat to the woods to enjoy the winter season.
Aerial view
Beautiful retreat to the woods to enjoy the winter season.
10.0 out of 10, Exceptional, (31)
"Very nice, well stocked and away from the hustle and bustle of city life. We had a great time."
Beautiful retreat to the woods to enjoy the winter season.
The Meadows House @ Otis Ridge w/ 7-person hot tub
Property grounds
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (20)
"Relaxing get away. Great hot tub, table shuffleboard. 3 floors of comfort."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Great Barrington Get Away
Fridge, microwave, oven, stovetop
Great Barrington Get Away
9.6 out of 10, Exceptional, (16)
"The house was exactly as advertised, comfortable, and with great location. We enjoyed a great weekend of skiing at both Catamount and Butternut, and the kids enjoyed their first ski lessons. We even got a few inches of snow to go with it. Howard was an excellent host, very easy to communicate and always reachable. We will be back for sure!"
The price is £414
includes taxes & fees
5 May - 6 May
Great Barrington Get Away
Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.
Fridge, microwave, oven, stovetop
Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.
10.0 out of 10, Exceptional, (1)
"We absolutely loved the place! Tons of space, all new appliances, fire pit and the gorgeous master bathroom were all highlights of our stay. Super convenient location within a few minutes of the Stop and Shop as well as other stores. Andrea was very friendly and attentive. She was there to quickly answer any questions we had and made sure we had everything we needed. Highly recommend!"
Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.
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See all available properties in Weatogue
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.

Other types of properties in Weatogue you may be interested in

The Red Lion Inn
Outdoor pool, pool loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (871)
"What a pleasure to have the opportunity to stay in an historic inn such as the Red Lion. "
The price is £116
includes taxes & fees
5 May - 6 May
The Red Lion Inn
Quality Inn
Lobby
Quality Inn
2.5 star property
8.0 out of 10, Very good, (881)
"Easy to check in and check out. The only small issue I had was that it was windy and the doors for the garbage outside kept swinging and make a bang noise when it opened and shut at night. "
The price is £79
includes taxes & fees
5 May - 6 May
Quality Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 star property
9.0 out of 10, Wonderful, (461)
"The room was spacious- 2 bedrooms, large living room, full kitchen, terrace, TV's in every room. It was spotless when we arrived. The stay was exceptional."
The price is £132
includes taxes & fees
8 May - 9 May
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
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.

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, apart-hotels, 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 £215 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?

Stockbridge Home, Come Experience The Berkshires!: This holiday home rental outside of Weatogue offers a balcony, a garden and a BBQ to help you feel perfectly comfortable 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.

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 Frissell and Taconic State Park 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.

Recent reviews of Weatogue properties
Expedia verified reviews

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

5/5 Excellent
"Really enjoyed the seating outside and pool side was very relaxing. The staff was very helpful and informative. Great experience!!!"
A verified traveller stayed at Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Posted 4 days ago
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel