Weatogue Holiday Rentals

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Holiday Rentals in Weatogue

Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, 32 reviews
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Waterview Home in the Berkshires: Near Hiking
9.2 out of 10, Wonderful, 14 reviews
"Lovely house and kind owner. We had a great time. The view is amazing."
Waterview Home in the Berkshires: Near Hiking
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, 29 reviews
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, 7 reviews
"We had a great stay while skiing for 2 days at nearby Catamount ski resort. The kitchen and house were fully stocked with all essentials. Netflix access enabled us to enjoy a family movie after a long day of skiing. Cozy house and quiet area.......nice to wake up to hear birds chirping!!"
The price is NZ$539
per night
30 Jun - 1 Jul
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, 8 reviews
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
8.8 out of 10, Excellent, 3 reviews
"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, 3 reviews
"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 - Largest Fresh Water Reservoir in Mass....
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, 49 reviews
"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 NZ$439
per night
24 Jun - 25 Jun
Perfect Vacation Get Away - Historical New Marlborough
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, 6 reviews
"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!
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
10.0 out of 10, Exceptional, 128 reviews
"We thoroughly enjoyed our stay at Joe and Lisa’s stunning barn. It is rammed full of character and is very well located to explore both the Hudson Valley and the Berkshires, just over the border in MA. Joe left us to enjoy the place in peace but was always on hand to answer any questions. The kids really enjoyed taking a dip in the hot tub and making s’mores over the outdoor fire pit. We will definitely return!"
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, 2 reviews
"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
10.0 out of 10, Exceptional, 4 reviews
"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
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, 2 reviews
"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...
The price is NZ$668
per night
16 Jun - 17 Jun
The Blue Elm - A Historic Berkshire Cottage
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, 20 reviews
"Relaxing get away. Great hot tub, table shuffleboard. 3 floors of comfort."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
9.8 out of 10, Exceptional, 6 reviews
"This house was awesome! Plenty of room and amenities for all! Great location to the downtown, local restaurants and bars. Communicating with the host was also so easy to do. Would definitely recommend for a weekend getaway!"
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, 39 reviews
"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!
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, 12 reviews
"We have a lovely stay, house is super clean and has all you need to relax and enjoy the space. I loved the fact we could take our small dog with us to make it a lovely family’s vacation. The house is central to everything and all towns in the Berkshires which we appreciated so much. We will return and would recommend to other highly also."
Stockbridge Home, Come Experience The Berkshires!
Peaceful, Post and Beam Loft, Sleeps 9
10.0 out of 10, Exceptional, 8 reviews
"beautifully stay for couples."
Peaceful, Post and Beam Loft, Sleeps 9
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, 22 reviews
"This home was "as advertised" - plenty of room. Nice neighborhood setting. Well stocked kitchen & nice outside area in the backyard / deck. We used it as a base camp for section hiking the appalachian trail."
The price is NZ$774
per night
19 Jun - 20 Jun
Cheerful 3-bedroom cottage with woodstove
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, 80 reviews
"We have 20 years experience renting homes for family gatherings and this is the most interesting and amazing property. Gardens galore, plenty of space to congregate or go off by yourself, fully appointed kitchen, and comfortable space. We were a party of ten and everyone loved the experience."
Antique Farmhouse Totally Restored
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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
3.5 star property
8.8 out of 10, Excellent, 889 reviews
"Always a great HISTORIC INN "
The price is NZ$358
per night
17 Jun - 18 Jun
The Red Lion Inn
Quality Inn
2.5 star property
8.2 out of 10, Very good, 912 reviews
"Our stay was excellent. I greatly appreciated the refrigerator and microwave in the room. The proximity to everything in Lee was marvelous."
The price is NZ$213
per night
18 Jun - 19 Jun
Quality Inn
Quality Inn
2.5 star property
8.2 out of 10, Very good, 1,009 reviews
"Really clean and great staff"
The price is NZ$187
per night
11 Jun - 12 Jun
Quality Inn
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Weatogue holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Weatogue. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Weatogue. Seeing all the best attractions is bound to make you fall in love with Weatogue. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Weatogue short-term rentals, that won’t be hard to do.

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?

Beautiful Getaway - Right on the Lake-Close to Skiing: This holiday home rental outside of Weatogue is located on the beach, and has a fireplace, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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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