Weatogue Holiday Rentals

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Holiday Rentals in Weatogue

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 reviews
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
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, 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
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior
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 HK$1,241
per night
30 Jun - 1 Jul
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
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Serene Acreage - Pond - Hiking Trails Nearby
Property grounds
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, 5 reviews
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
The Blue Elm - A Historic Berkshire Cottage
Exterior
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 HK$1,951
per night
25 Jun - 26 Jun
The Blue Elm - A Historic Berkshire Cottage
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 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.
Perfect Vacation Get Away - Historical New Marlborough
Property grounds
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 HK$1,171
per night
25 Jun - 26 Jun
Perfect Vacation Get Away - Historical New Marlborough
Waterview Home in the Berkshires: Near Hiking
Outdoor dining
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
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
Fridge, microwave, stovetop, dishwasher
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
9.4 out of 10, Exceptional, 6 reviews
"Cute cabin in a beautiful private setting. Very peaceful and surrounded by nature."
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
Private Estate, Heated YEARROUND Outdoor Pool
Fridge, microwave, oven, stovetop
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
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, 21 reviews
"The rental property was just as described online. We had a very relaxing time. We also enjoyed playing all the games provided. This is a beautiful location and very quiet area. We loved sitting out in the hot tub at night looking up at the stars. Really special experience."
The Meadows House @ Otis Ridge w/ 7-person hot tub
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 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!
'The Mill River Cabin’ w/ Fireplace & River View!
View from property
'The Mill River Cabin’ w/ Fireplace & River View!
9.8 out of 10, Exceptional, 32 reviews
"Cozy cabin, perfect for the two of us and our dog. Nestled in the woods with an active stream running by! We loved the quirky interior decor! Philippe was a great host and easy to work with."
'The Mill River Cabin’ w/ Fireplace & River View!
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Fridge, oven, stovetop, dishwasher
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
10.0 out of 10, Exceptional, 2 reviews
"The barn was amazing and just perfect for our weekend away. Ricky was really great to communicate with and very responsive. We can’t wait to go again soon!"
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Berkshires Cabin 2 Mi to Appalachian Trail!
Interior
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!
Peaceful, Post and Beam Loft, Sleeps 9
TV, DVD player
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
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Exterior
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, 140 reviews
"Perfect home on Otis Lake with plenty of room for a group of friends to gather. Kitchen was fully stocked with all the utensils, pots/pans, dishes to make a nice meal. Beds were very comfortable. Plenty of outdoor furniture to gather near the fire pit by the lake. Keurig coffee maker available to make coffee in the morning. Nice and quiet, felt very private. Plenty of room for parking. Thanks for letting us rent."
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Antique Farmhouse Totally Restored
Exterior
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
Beautiful retreat in a lake community to the enjoy the summer season.
Aerial view
Beautiful retreat in a lake community to the enjoy the summer season.
10.0 out of 10, Exceptional, 31 reviews
"Very nice, well stocked and away from the hustle and bustle of city life. We had a great time."
Beautiful retreat in a lake community to the enjoy the summer season.
Great Barrington Get Away
Fridge, microwave, oven, stovetop
Great Barrington Get Away
9.6 out of 10, Exceptional, 17 reviews
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is HK$2,732
per night
7 Jul - 8 Jul
Great Barrington Get Away
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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, 902 reviews
"This property was very special and the staff were very good. "
The price is HK$1,251
per night
7 Jul - 8 Jul
The Red Lion Inn
Quality Inn
Lobby
Quality Inn
2.5 star property
8.2 out of 10, Very good, 922 reviews
"Great little hotel! Staff was great and very accommodating. Very clean and good price."
The price is HK$989
per night
7 Jul - 8 Jul
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, 486 reviews
"Was quite surprised with the facilities and the wonderful accommodations. Will definitely return in the near future."
The price is HK$1,163
per night
24 Jun - 25 Jun
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.

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:

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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?

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.

Recent reviews of Weatogue properties
Expedia verified reviews

The Briarcliff Motel

The Briarcliff Motel

5/5 Excellent
"Liked everything about it"
A verified traveller from NEW YORK stayed at The Briarcliff Motel
Posted 6 hours ago
The Briarcliff Motel