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Compare 66 Cottages in Weatogue with updated reviews, rates, and availability.

Private Island - Largest Fresh Water Reservoir in Mass....
Aerial view

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....
Idillic summer getaway in Litchfield Hills, CT.
Property grounds

Idillic summer getaway in Litchfield Hills, CT.

10.0 out of 10, Exceptional, (13)
"The place was as described and very comfortable. We enjoyed our stay!"
Idillic summer getaway in Litchfield Hills, CT.
East Otis Vacation Rental w/ Private Deck & BBQ!
East Otis Vacation Rental | Studio | 1BA | 800 Sq Ft | Steps to Enter

East Otis Vacation Rental w/ Private Deck & BBQ!

9.6 out of 10, Exceptional, (7)
"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"
East Otis Vacation Rental w/ Private Deck & BBQ!
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Living area

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

3.0 star property
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Perfect Vacation Get Away - Historical New Marlborough
Exterior

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (54)
"It was a pleasure to find this gem of a cabin available for a night so we could attend a concert at Tanglewood, despite living out of state. The location was lovely, convenient and quiet; the cabin was impeccably appointed (thanks for the fresh flowers in every room and bottle of Riesling!) and very clean with every possible amenity; and the hosts were communicative, friendly and helpful. Overall, this was an idyllic mix of quaint/cute/unique and function/comfort/ease. I will absolutely seek out...
Perfect Vacation Get Away - Historical New Marlborough
The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (7)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
The price is AED 735
AED 1,526 total
includes taxes & fees
3 Jan - 4 January 2025
The Blue Elm - A Historic Berkshire Cottage
Cottage is currently rented for the year, and not available until further notice
Exterior

Cottage is currently rented for the year, and not available until further notice

9.0 out of 10, Wonderful, (2)
"This is a lovely property in a perfect, serene location. Highly recommend!"
Cottage is currently rented for the year, and not available until further notice
Two Bedroom Cottage Close To Town
Exterior

Two Bedroom Cottage Close To Town

9.4 out of 10, Exceptional, (19)
"We enjoyed three nights at the cottage. It's beautifully decorated, comfortable, warm and welcoming - a perfect home base for nearby hikes and exploring the area. The large yard was perfect for playing soccer with our child. Renters note: we also had a fabulous meal at nearby restaurant Fern. "
Two Bedroom Cottage Close To Town
Quiet rustic cottage with shared lake access

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (103)
"I am originally from Western Mass, and was looking for a quiet get away for my fiancé and I for my birthday weekend. This more than fit the bill, we had many romantic nights in front of the fire (big y or tractor supply good for indoor wood). The cabin was delightful, quaint. And it was so quiet this time of year with no one else around us, which was just what I was looking for. Our hosts were great, made everything very easy for check in and check out and were easily valve through the App....
Quiet rustic cottage with shared lake access
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Main deck

The Cottage at Highland Lake, year-round, waterfront with a boat dock

10.0 out of 10, Exceptional, (4)
"Jeanne was wonderful to work with and very responsive when we booked our last minute get away. Location is ideal - we brought our kayaks and very easy launching area. Would definitely not hesitate to come back to the same spot. Thanks for sharing your home with us. "
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Fun Getaway Lakehouse in the Hudson Valley
Tiny house for glamping! Sleeps 2 and fire pit!

Fun Getaway Lakehouse in the Hudson Valley

10.0 out of 10, Exceptional, (14)
"Beautiful clean property. A lovely location. Exceeded expectations."
Fun Getaway Lakehouse in the Hudson Valley
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Monterey Vacation Rental | 3BR | 1BA | 900 Sq Ft | Stairs Required

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

10.0 out of 10, Exceptional, (3)
"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Relax on the large deck with lake views

Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!

10.0 out of 10, Exceptional, (5)
"Very clean, cute house right on the lake. We enjoyed our time there. "
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Peaceful Goshen Cottage w/ Screened Porch & Views!
Goshen Vacation Rental | 3BR | 1.5BA | 1,500 Sq Ft | Stairs Required for Entry

Peaceful Goshen Cottage w/ Screened Porch & Views!

9.0 out of 10, Wonderful, (29)
"Enjoyed our stay very much. The accommodations suited our needs. Appreciated the cleanliness of the property and the ease of checking in/out."
Peaceful Goshen Cottage w/ Screened Porch & Views!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Property grounds

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Modern Cozy Cottage, Games, Fireplace. 20 min to Hudson & Catamount Skiing
Living area

Modern Cozy Cottage, Games, Fireplace. 20 min to Hudson & Catamount Skiing

10.0 out of 10, Exceptional, (2)
"My family of four stayed at this house for a wedding in the area. The house was more than we expected. Very comfortable, good feel, and just an overall good experience."
Modern Cozy Cottage, Games, Fireplace. 20 min to Hudson & Catamount Skiing
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
New Marlborough Vacation Rental | 1BR | 1BA | 750 Sq Ft | Stairs Required

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (37)
"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
A Charming Cottage - Secluded in Nature and Relaxing
Exterior

A Charming Cottage - Secluded in Nature and Relaxing

10.0 out of 10, Exceptional, (3)
"The rental was nice. It was convenient for viewing the fall foliage and just enjoying the countryside. "
A Charming Cottage - Secluded in Nature and Relaxing
Waterfalls and Trails at 'the Mills At Green Hole'
Exterior

Waterfalls and Trails at 'the Mills At Green Hole'

3.0 star property
Waterfalls and Trails at 'the Mills At Green Hole'
Underhill Cottage
Interior

Underhill Cottage

Underhill Cottage
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.
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Other property types in Weatogue

Antique Farmhouse Totally Restored
Sunrise lights up the front of the house. Moon sets over the mountain.

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored
Private Estate, Heated Yearround Outdoor Pool

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (14)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
Private Estate, Heated Yearround Outdoor Pool
Berkshires Cabin 2 Mi to Appalachian Trail!
Otis Vacation Rental | 3BR | 2BA | 1,200 Sq Ft | Stairs to Access

Berkshires Cabin 2 Mi to Appalachian Trail!

9.6 out of 10, Exceptional, (10)
"The hosts were extremely responsive and helpful, providing us with hiking ideas, questions regarding the house and suggesting best shopping spots for incidentals. The living room was cozy, seating five comfortably. The kitchen was well stocked so cooking a Thanksgiving meal was a pleasure. We thoroughly enjoyed ourselves."
Berkshires Cabin 2 Mi to Appalachian Trail!
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.

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