Places to stay in Pleasant Valley

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Top-rated places to stay in Pleasant Valley

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Top guest favorite

Guesthouse in Woodstock

5 out of 5 average rating, 381 reviews

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

PRIVATE Modern/Rustic Apt WALK TO TOWN 5 * Rating "premiere" NO EXTRA CHARGES! 1000 sq ft Pet Friendly n/c Park Master King Suite &I can put up 2cots /crib Full Kitchen Cathedral Living Room w/Mountainview. 1&1/2 Bath Deck for Outside Dining w/Mountainview WOOD FIREPLACE ondeck Wi-Fi Wash/Dryer Gas BBQ Steps to CTR of Town Green & NYC Bus-stop, THE COLONY, Yum Yum, Goodnight , Garden Cafe, Silvias, Bread Alone, Mud Club, Station Bar, shops . Cemetery's Bubbling Stream, PrivatePlayground

Top guest favorite

Home in Wappingers Falls

4.97 out of 5 average rating, 29 reviews

Caroline House Beacon Getaway

Set just outside Beacon in a beautiful, quaint neighborhood, this is the perfect retreat for family and friends after a fun day at all of the local attractions. Enjoy the large outdoor space with firepit, grill, hammock and deck or any of the close by farms, breweries, downtown Beacon and the many Hudson River adventures. Just 7 minutes from the Beacon MTA train and I84 with all the excitement at your fingertips set in a beautiful neighborhood where you may spot our neighbors horses roaming

Guest favorite

Apartment in Stockbridge

4.96 out of 5 average rating, 104 reviews

Historic,Famous,Iconic, Unforgettable Berks Escape

PICTURE IT...You can put yourself in the "famed" Norman Rockwell Main Street at Christmas Painting! That's Right,Cozy, Intimate,Magical and all to yourself.Fully equipped with all the comforts of home. Small Town Charm,Big time Historic setting in the heart of Downtown Stockbridge! Spend your afternoon sipping Tea or Wine looking out the iconic picture window Norman Rockwell installed himself. The one where the Christmas Tree Glows in a room that was Norman Rockwell's Studio from 1953-1957

Superhost

Apartment in Kingston

4.76 out of 5 average rating, 119 reviews

In the Heart of Kingston

Pet friendly. A comfortable apartment in the heart of midtown Kingston. Enjoy a cup of coffee in the garden, or curl up with a book in the window seat in the living room. This apartment is a great spot to relax from a day of exploring Kingston. You will be close to everything when you stay at this centrally-located place. Note: located near a train; so if you are a light sleeper, it might not be a good fit. Garden area is still in winter mode (until May 15th), so please excuse the mess.

Top guest favorite

Home in Mount Tremper

4.92 out of 5 average rating, 191 reviews

Rippleside Retreat - Stay and Relax

LOCATION, LOCATION! Spacious and quiet creek-front and mountain view home. Near Phoenicia and Woodstock for shopping, browsing art galleries, and fine dining. Plenty of hiking trails, fishing, and tubing in the warmer months, and close to skiing at Belleayre, Hunter, Windham, and Plattekill Mountains for winter enthusiasts. The home is conveniently located near the Emerson Resort and Spa, Foxfire Mountain House, Howland House, Mount Tremper Arts, and Onteora Mountain House wedding venues.

Guest favorite

Home in Sheffield

4.91 out of 5 average rating, 117 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Top guest favorite

Guesthouse in Bethel

5 out of 5 average rating, 16 reviews

Tranquil getaway cottage in charming neighborhood

Escape the city bustle and unwind in the tranquility of The Red Cedar Cottage nestled between Bethel and Newtown, just a short drive from Danbury, CT. Tucked away in a peaceful neighborhood, this fully renovated cottage offers a serene getaway for couples seeking relaxation. Unwind in style on a high-end king-sized mattress in a whimsically curated space designed to rejuvenate your senses. Discover the Red Cedar Cottage and immerse yourself in a tranquil escape from the ordinary.

Guest favorite

Home in Phoenicia

4.93 out of 5 average rating, 163 reviews

Heart of Phoenicia: Serene. Cozy. Close to all.

"Such a cute place with cabin-in-the-woods vibes but all the conveniences of being in town." What Shannon said in a 5 star review after her stay. I couldn't have put it better. Relax and reconnect in this calm and quiet little house nestled in the center of our cool village. You're on the doorstep of hiking trails with breathtaking views and gorgeous trout streams. Lounge around a glowing campfire in the back yard with S’mores or spin viny. On NYC bus route and ski shuttle.

Superhost

Farm stay in Kent

4.86 out of 5 average rating, 314 reviews

(°) The Wandering Peacock (°)

The Wandering Peacock is a unique lodging experience. Outdoor spa, with a cedar hot tub and views of the Appalachian Trail, wood-burning sauna with herbs from the garden. The house showcases vintage machinery, a library, an outdoor kitchen with a pizza oven, and much more. Nestled within the forest foothills of the Appalachia trails, this converted barn is minutes away from downtown Kent and just walking distance from Bulls Bridge, the local river, and waterfalls.

Top guest favorite

Guest suite in Newburgh

4.92 out of 5 average rating, 168 reviews

Cozy Country Efficency in Hudson Valley

Spacious and cozy one bedroom efficiency Warm and welcoming, sparkling clean nestled in The Hudson Valley all the amenities of a hotel stay, but the comfort of your own space Farm markets, Wineries, Craft beer through out the area. Historic sights to visit or outdoor activities all around ( hiking, skiing, kayaking, bike riding,etc) Stay in and cook in well appointed kitchenette or sample the large variety of excellent restaurants throughout the region

Superhost

Apartment in Saugerties

5 out of 5 average rating, 3 reviews

Creekfront I Hot Tub I Sauna I Fire Pit I Kayaks

Welcome to Upstate Waterfronts! Looking for a restorative Upstate getaway? This Creekside gem has you covered. - HOT TUB - SAUNA - 3 bedrooms/ 1 full bathroom - Fully equipped kitchen & high-end amenities - Private creek access - including kayaks/vests/paddles - Stunning creek views - including a water facing balcony - 3,000 Arcade games, 75'' Smart TV, endless board games - High-speed WiFi - Prime location - walkable to town/restaurants/shops/beach

Top guest favorite

Chalet in Craryville

5 out of 5 average rating, 13 reviews

Lockwood Lodge Mountaintop

Welcome to our slice of paradise in the Hudson Valley! Enjoy a secluded hilltop home with beautiful mountain and valley views, surrounded by 18 acres of woods. The open floor plan is perfect for cooking or relaxing in front of the fire, and enjoy grilling and the pool when the weather is right. The location is minutes from Hillsdale, and a 15-20 minute drive from Hudson and Great Barrington, with amazing restaurants and activities for every season.