Holiday rentals in Iona Island

4.85 out of 5 average rating, 543 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, 171 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.

4.96 out of 5 average rating, 320 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, 190 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!

4.9 out of 5 average rating, 192 reviews

Home in Peekskill

The Peekskill RiverView House

The Peekskill RiverView House A fully renovated dream house overlooking the historic Peekskill Bay. This 3 bedroom 3.5 bath designer house is a 5 minute walk to the train station as well as the historic downtown. It’s truly the gateway to the Hudson Valley along with having the walkable access to culture, hiking, biking, culinary, spa, and entertainment activities within City limits. Expansive decks on all 3 floors with spectacular Hudson River views from every room.

4.99 out of 5 average rating, 317 reviews

Treehouse in Wallkill

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

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.

Guest suite in Haverstraw

4.94 out of 5 average rating, 365 reviews

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

4.98 out of 5 average rating, 127 reviews

Loft in Mountainville

Lovely, Quiet and Very Private! Entire Loft!

Nestled in the mountains is a peaceful place to lay your head. Just a stones throw from vineyards, brewery's and some of the best views and attractions the Hudson Valley has to offer. Here you'll find a private & secluded bedroom and bathroom fit for 2. A small "kitchenette" is avaliable for use as well as an outdoor seating area with fireplace. Free parking in designated spot. Waterfall is a short hike away.

4.92 out of 5 average rating, 276 reviews

Guest house in Peekskill

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

4.99 out of 5 average rating, 203 reviews

Cottage in Philipstown

Modern Country Cottage by Bear Mountain

Wake up feeling rejuvenated in a lofted bedroom beneath a wood-paneled ceiling with skylight windows. Descend a spiral staircase into a warm kitchenette for a cup of coffee, then have a seat in an airy living room beside a brass-plated decorative fireplace. Enjoy a picnic or grill on the front lawn and explore the 4 acres of most authentic Hudson Valley landscape.

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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4.96 out of 5 average rating, 166 reviews

Cottage in Putnam Valley

Private Lake House 1 Hour to NYC & Near Westpoint

MadelineRating, 5 stars1 week 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.

4.73 out of 5 average rating, 152 reviews

Home in Philipstown

Bungalow near West Point on Hudson River

RobinRating, 5 stars1 week ago

Loved being on the river. Cute bungalow. Easy to get around Hudson Valley sites. Near cute Cold Spring. A/C worked well. Loved having BBQ and eating out in the backyard by the Hudson River. Also watching the boats go by! Thanks much!!

4.99 out of 5 average rating, 90 reviews

Cabin in Greenwood Lake

Modern Nordic Designed Cabin

FeRating, 5 stars2 weeks ago

The Nordic Cabin was the perfect setting for my husband and I to celebrate our 22nd wedding anniversary. The cabin is beautiful and the modern design, furnishings, and decor really stand out. Instructions of how to get into the cabin and the pitcures provided made check in and check out a breeze. The kitchen was well stocked. A bottle of white wine and a few treats were left for us. The kitchen offered different spices, oils, milk, and eggs. Kitchen utensils, pots/pans, dishes, cups, glasses, etc are provided, as well as cleaning supplies. The bathroom was stocked with toiletries. We spent a lot of time relaxing in the cozy living room and slept well in the beautiful bedroom. Last, I have to say that the first time we opened the gate at night, after dinner in Warwick, and saw all of the outdoor lights on, really made it feel like we were entering an enchanted garden. Would definitely come back!! Thank you Kamil and Margaret!!

4.94 out of 5 average rating, 87 reviews

Cottage in Putnam Valley

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

AlexRating, 5 stars1 day ago

My family and I had an incredible time in this beautiful house, everything in order and I loved every space of this house, very happy we will be back

5 out of 5 average rating, 38 reviews

Cabin in Saugerties

Luxury A-Frame Cabin w/ Hot Tub

AmandaRating, 5 starstoday

We had a serene and luxurious stay at Fil and Ellie’s. The inside of the home is comfortable and they seem to have thought of every detail. We so enjoyed the peace and quiet, the views of the beautiful trees, and our soaks in the tub. This felt like a private oasis- a true slice of heaven.

Flat in Highland Falls

4.8 out of 5 average rating, 134 reviews

Cozy 1-bedroom retreat minutes from West Point!

AlexRating, 5 stars1 month ago

smooth, private, & responsive. would definitely book again if i’m in the area

Home in Philipstown

5 out of 5 average rating, 9 reviews

Arkadia House Mid-century retreat with pool & view

AriRating, 5 stars71 months ago

Dan and Andrew were great hosts and very easy to communicate with. The location was beautiful and the views were amazing. The house was stocked with everything you could possibly need; towels, bedsheets, blankets cookware, a bunch of basic food necessities & more. The pool was refreshing after laying in the sun and watching the sunset from the pool is truly a must when visiting this home. We would love to stay here again and highly recommend to others looking for a gorgeous getaway home.