Holiday rentals in Graymoor

4.93 out of 5 average rating, 132 reviews

Home in Philipstown

Cozy 3 bedroom house on quiet private road

3 bedroom house overlooking creek on a quiet, private road. Minutes from Metro North Railroad, Hudson River, historic Cold Spring Village, Highlands Country Club golf course, Beacon, downtown Peekskill, Bear Mountain State Park, Boscobel House & Gardens, Fahnestock State Park and West Point Military Academy. Restaurants, farmer’s markets, hiking trails. We are dog friendly but there is an additional fee of $80 per stay. I live close by so I’m available for help or assistance during your stay.

4.99 out of 5 average rating, 197 reviews

Cottage in Cortlandt

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

4.94 out of 5 average rating, 141 reviews

Cottage in Cold Spring

Cheerful Private 3 Bedroom Cottage in Cold Spring

Relax with friends & family at this peaceful forrest cottage, just 7-minutes outside of The Historic Village of Cold Spring on a beautiful, quiet country road. Much bigger on the inside than it looks, this place has what you need: fresh linens, full kitchen, wifi, streaming tvs and plenty of great books to read. There is a trampoline in the backyard & patio lights for Spring/Summer/Fall nights dining outside. Rent alone or pair with my cottage next door: Peaceful Yellow Door Cottage on Airbnb.

4.85 out of 5 average rating, 539 reviews

Loft in Cornwall

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

4.8 out of 5 average rating, 170 reviews

Flat in Peekskill

Little haven by the woods

This is a walk-out basement with two private entrances, and it’s own private outside area. The patio has comfy furniture with a bbq. The kitchen is small, yet efficient with large windows. The bedroom is cozy and comfy with a large smart tv on the wall. The bedroom has a 3/4 wall dividing it from the rest of the apt, but no actual door. So it could be considered a “studio”. We are steps from the trail heads into Blue Mt park. We’re also walking distance to the metro north & downtown.

4.95 out of 5 average rating, 235 reviews

Guest house in Mahopac

Lakeview Guesthouse with Sauna

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ dining/ takeout options + boba tea! Drivable to farm fresh food markets, restaurants and art museums. Cedar dry Sauna on property for use. Nearby towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to trails of Volz park!

4.96 out of 5 average rating, 319 reviews

Guest suite in Chester

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, French door shower, and a kitchenette with sunny breakfast nook. It's freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

4.86 out of 5 average rating, 189 reviews

Flat in Newburgh

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Guest house in Cold Spring

4.99 out of 5 average rating, 164 reviews

Modern+bright forest escape - near village & train

Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural light.

4.96 out of 5 average rating, 114 reviews

Guest suite in Cornwall

Studio in Cornwall

Located near the village, hiking trails, Jones Farm, Hudson River, Woodbury Commons, West Point and more. The studio is ground level with a private entrance. The kitchenette incudes a convection toaster oven, a hot plate cooktop with pots/pans, light kitchenware, coffee maker, & fridge. Also provided: TV, Roku stick, Wi-Fi, AC/electric heat. (No cable) This is our home. The use of illicit drugs, smoking and excessive alcohol is prohibited.

4.91 out of 5 average rating, 204 reviews

Cottage in Mohegan Lake

The Pearl of Westchester

Welcome to the Paradise! This Pearl of Westchester are nested with a Main house on private 2 acres of direct waterfront estate. Offering a private dock and beach in a flawless natural paradise. Enjoy swimming, fishing, boating or barbecuing on a private porch. Hiking in walking distance Located less than an hour away from NYC. Peekskill Metro North is 15 min away.

4.98 out of 5 average rating, 100 reviews

Home in Highland Falls

Bear Mountain, Westpoint, & Hikers Retreat

The Fort @Fort Montgomery, Westpoint/Bear Mountain New to the rental market! This recently renovated 900 Square foot single story home located 5 miles/7 mins from West Point Military Academy and 3 miles/ 3min from Bear Mountain is the ideal spot for friends and family to convene for a weekend visit in the Hudson Valley.

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Other great holiday rentals in Graymoor

4.99 out of 5 average rating, 315 reviews

Treehouse in Wallkill

The Treecastle at the Roundhouse Homestead

ShannonRating, 5 stars1 day ago

Absolutely beyond pleased with our stay at the tree castle. Such a magical little getaway! The hosts are spectacular with communication and meeting your every need, and went above and beyond with supplying creature comforts and fresh baked goods (that are to die for!). The tree castle was so clean and stayed nice and cool despite the summer heat, even the outdoor bathroom was sparkly clean and a pleasure to use. We would come to stay again in a heartbeat, thank you for everything Dan and Melissa! And thank you for the delicious honey and letting us meet your chickens!! 🐓🐝💕💐

4.96 out of 5 average rating, 166 reviews

Cottage in Putnam Valley

Private Lake House 1 Hour to NYC & Near Westpoint

MadelineRating, 5 stars4 days ago

Benjamin's place is all you expect and more. It is clean, roomy, comfortable, and quiet. My family is all about comfortable temperatures and the AC makes each room feel great. If you are sitting on the deck, off the kitchen, there is a breeze with pretty sunrises and sunsets. Ben was a thoughtful host! I reached out with one simple question and before we knew it we had items delivered to the door - for our family and our dog! It was a delightful and welcoming touch. The cottage is so comfortable with fabulous bedding, a fantastic Jacuzzi tub, a fully stocked kitchen, and a full coffee and tea bar! Such a generous amenity. I highly recommend Benjamin's cottage.

4.94 out of 5 average rating, 83 reviews

Cottage in Putnam Valley

Peaceful Cottage with Grill | Walk to Lake

GaryRating, 5 stars2 months ago

This is a wonderful place. My wife and I loved it.

4.92 out of 5 average rating, 48 reviews

Flat in GARRISON

Modern Luxury King One-Bedroom

ScottRating, 5 stars2 weeks ago

This is our second time staying in the Hummingbird Suites within the last few weeks, that's how much we enjoyed it! We have stayed in both suites and it's hard to say which we liked more as they're both great. This one gives you a separate bedroom which is nice (and Jeff was generous enough to put a TV in there as well) and a beautiful open kitchen. Jeff has thought out everything so that it's always easy to find something (great labeling) and has accounted for everything that you might need during your stay. The location is also perfect! 10 minutes to Cold Spring, 15 to Peekskill, and it's easy to go across the river as well. Tons of hiking all around. It's a great place to stay to explore the area! We felt right at home with the cozy amenities and felt it was a great place to rest in-between our activities.

5 out of 5 average rating, 10 reviews

Home in Putnam Valley

Dr. Ruth’s Serene Lake Retreat

EvanRating, 5 stars5 months ago

After using Airbnb for years now no other place was a perfect 10. The lake house was simply great. Not only the physical status but the follow up and generosity of the hosts where beyond. We didn’t want to leave.

4.88 out of 5 average rating, 41 reviews

Cabin in Carmel Hamlet

Peaceful Forest Cabin

ChristopherRating, 5 stars1 week ago

Lanthe and Josephine’s cabin was an absolute dream. From the moment we arrived, we felt completely at peace. The space is warm, thoughtfully decorated, and nestled in such a serene location, perfect for a quiet getaway from the city. Everything was clean, cozy, and exactly as pictured. You can truly feel the love and care that went into creating this space. It was the perfect setting to relax, reconnect, and make meaningful memories. Thank you both for being such gracious and welcoming hosts. We’re already looking forward to returning!

4.78 out of 5 average rating, 230 reviews

Cottage in Cold Spring

Cozy Countryside Cabin Spa/Fireplace/Enclosed Yard

EdgarRating, 5 stars4 days ago

Very nice peaceful places and very good service i will definitely be back soon, thank you