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Craryville Rentals

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115 Houses

Escape to Avalon Cottage in the Hudson Valley

Craryville house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$166

The Barn at Copake Lake

Craryville barn

3 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$685

My Country Home

Craryville house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 14 minutes

Price per night from

$177

Great rentals within 20 miles that match your search

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$199

Evergreen Pines Country Estate Villa

Ancram house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$2,644

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

Price per night from

$238

The FarmHouse

Millerton house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$332

(FAKE - DO NOT BOOK THIS) Sleek, Modern Apartment - Steps from Hudson River

Athens apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$146

Babbling Brook Retreat

Lakeville apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$306

Iris Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$200

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$177

Country estate on 100 acres perfect for families

Chatham house

4 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$1,328

The Warehouse

Saugerties studio

Studio / 1 bathroom / sleeps 4

Price per night from

$200

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,263

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$186

Beautifully Renovated Berkshires Farmhouse

West Stockbridge b&b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$267

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$937

Chalet near 4 ski resorts with hot tub

East Chatham house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 16 minutes

Price per night from

$618

Mrs. Pleasant’s Plant Based B + B

Athens house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$199

Historic Gem Near Hudson, NY

Stuyvesant house

1 bedroom / 2 bathrooms / sleeps 3

Price per night from

$362

Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 22 minutes

Price per night from

$454

SAUGERTIES, New York... on SKI ROUTE

Saugerties house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 17 minutes

Price per night from

$177

Beautiful country estate offers two bedroom apartment.

Palenville apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$213

A Peaceful Escape

Leeds house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 25 minutes

Price per night from

$112

Lake House

Lakeville house

5 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 46 minutes

Price per night from

$701

Outdoor getaway hunting,fishing,skiing..relaxation

Copake house

3 bedrooms / 2 bathrooms / sleeps 9

“Home Away from Home ~ A great place to gather11” Had family coming from New York, Massachusetts and Connecticut to celebrate my birthday ~ hotels, motels are expensive, and they're not home. This house offered a great place to convene ~ outdoor gas grill, eating on the deck, well stocked kitchen and cozy living room. Spacious, comfortable with a lovely master bedroom with private bath. All bedrooms are located somewhat away from the living room which is nice. Walked to the lake with paddles and canoed with my son; got great coffee at the nearby General Store. Michael is wonderful to rent from and very accommodating.

Responds fast! avg. 6 minutes

Price per night from

$222

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$327

OUR LOVELY VACATION HOME IS LOCATED IN THE CATSKIL

Catskill finca

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 12 minutes

Price per night from

$584

Beautiful Home on The Esopus Creek

Saugerties house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$290

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

1 bedroom / 1 bathroom / sleeps 3

“Perhaps the most relaxing vacation I've ever had” The Sigels' cottage was absolutely perfect for us. My husband and I were looking for a nice quiet 4-night stay while our 7-yr-old twins visited with their grandparents. When we arrived everything looked just as in the pictures. The room is sunny, but stays nice and cool too (we were there in august). There is an overhead fan but we didn't even need it. The Sigels made us feel very much at home, but they also seemed to know that we were not looking for a chatty B&B; experience. There are plenty of little touches like a bottle of wine waiting for us, tea, sugar, and some other basics in the kitchenette. A hair dryer, eye shade in the bedside table, etc. But nothing seemed overly fussy-- they are naturally good hosts. The pool was absolutely perfect. Big enough to swim laps, but small enough to be a nice temperature. We spent one whole morning just floating in the pool. The view from the pool is stunning. I am sure there are some amazing hikes around (I had broken my tailbone so hiking will have to wait for next year). Great Barrington is a wonderful town too, so if you're wondering where to stay in the Berkshires, then you would be wise to choose GB. It's not huge, but we never really left town. The walkable part of town has great diners, a cool little coffee shop, a movie theatre, used book store, and great music and food at the Gypsy Joynt (a member of the family that owns it-- Jordan Weller-- put out the best CD I've heard in a long time!) On our last night there the Sigels suggested we go to the Guthrie Center for an open mic where we heard more great music. I can't say enough about the Seigel's cottage. We can't wait to go back next summer.

Price per night from

$270

Catskill NY/ 2 Bedroom Cottage on Cauterskill Crk

Catskill cottage

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$264

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 29 minutes

Price per night from

$290

LOVELY SAUGERTIES RENTAL (Pool)

Saugerties house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$493

Charming 2+2 Lakeside Cottage on Best Lake in CT

Salisbury cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$205

Private Apartment at Stony Ledge

Saugerties apartment

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$172

Esopus Bend Getaway 4 min to HITS

Saugerties apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$168

Berkshire Farmhouse Vacation

West Stockbridge house

5 bedrooms / 2 bathrooms / sleeps 15

“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the living room and paneled walls in the dining room. We were there on a rainy, cold weekend, so did not have an opportunity to enjoy the grounds or porch, but imagine it would be lovely in the warmer weather. Elaine (and her shop) were on the same grounds and she was available for questions about the area. Overall a very relaxing & convenient experience.

Price per night from

$296

The Artist's House - Special Winter Rates!

Hudson house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 31 minutes

Price per night from

$400

Viewing 38 of 115
rentals in Craryville

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