Places to stay in Fort Montgomery

4.99 out of 5 average rating, 195 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

4.99 out of 5 average rating, 297 reviews

Tiny home in Wallkill

Get Away to "Hygge" Tiny House on 75 Private Acres

Escape to 75 acres of secluded, private land and lounge in this "hyggelig" tiny house. The house has everything you need, from heat and A/c, strong wifi, TV with streaming (sign in to Netflix, HBO, etc), full working kitchen (gas stove, oven, microwave), shower and bathroom. This tiny house has an incredible amount of light coming in from the very large windows throughout. Outdoor amenities include wood patio, propane bbq grill, dining table/chairs, fire pit. Lawn games available on request.

4.96 out of 5 average rating, 318 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.

Apartment in Marlboro Township

4.98 out of 5 average rating, 376 reviews

Cliff Top at Turtle Rock

Cliff Top retreat with a one hundred mile view of the Shawangunk's and the Catskill Mountains, surrounded by thousands of acres of ancient forest. Conveniently located in the Hudson Valley Wine and Orchard country. Twenty minutes from Beacon and New Paltz. Furnished with mid-century and 18th century period furniture and art work, yet with all the modern conveniences. Uber and Lift an easy five minutes away. The ancient forest contains many Stone Age rock shelters and calendar sites.

4.97 out of 5 average rating, 120 reviews

Barn in Mountainville

Renovated Red 1890’s Hudson Valley Barn

Renovated barn in Mountainville, NY at the base of the Schunnemunk hiking trails. 1 mile from Storm King Art Center. 3 miles to Cornwall. 10 minutes from Woodbury Common Premium Outlet. 15 minutes to West Point. Private stairs & balcony leads to 500 square foot second-story space. You get the entire upstairs to yourself. The NYS Thruway does run between the house and the mountain. There is highway noise. TV has a ROKU. The WiFi signal is weak due to the metal siding on the barn.

4.9 out of 5 average rating, 190 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.

4.96 out of 5 average rating, 107 reviews

Condo in Highland Falls

Cozy West Point Hide Away and Cadet’s Get Away

Newly renovated basement space in a very quiet secluded neighborhood with a full kitchen, full size bathroom, Fast WiFi, Smart TV, Separate parking, walking distance to Hudson River, Main Street, Bear Mountain State Park, West Point Military Academy and several adventurous hiking trails. For those who like to shop we are located only 20 minutes to the Woodbury Commons and only a 45 minute drive to NYC. Also Stuart International Airport is only a short drive from here.

4.93 out of 5 average rating, 219 reviews

Home in Wappingers Falls

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. Be our guest at our beautiful home located on the widest part of the Hudson River. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door.

4.92 out of 5 average rating, 173 reviews

Apartment in Newburgh

Ela - a 1 Bed Escape, Washer/Dryer in Unit

Kick back and relax in this calm, stylish space. Located on the second floor of a historic Newburgh building, this apartment features scenic views from oversized windows, in-unit laundry, LED TV & Fios WiFi, and designer furnishings. Queen bed with Casper mattress. Two flights of stairs required. The neighborhood is quiet, with tree lined streets and historic mansions nearby, just 2 blocks always from the Hudson River waterfront.

Farm stay in Fort Montgomery

4.98 out of 5 average rating, 194 reviews

Secluded overlook cottage near West Point

This quaint little house trailer is located on a secluded horse farm in the beautiful Hudson Valley only 50 minutes from NYC and less than 10 minutes from West Pt. Situated on a mountain top, this private little space is a nature lovers paradise. Come, recline on the new outdoor deck, relax by the fire pit and hike/explore the forest trails right out the front door.

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.

4.99 out of 5 average rating, 202 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.

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Other great vacation rentals in Fort Montgomery

Apartment in Cornwall-on-Hudson

4.92 out of 5 average rating, 108 reviews

Quaint Apartment in Cornwall on Hudson

LindaRating, 5 stars1 week ago

We enjoyed our stay at Carl’s, the place was spotless, comfortable and very cozy. The hosts were proactive with communication making check in seamless. Awesome to have parking right near the entrance and the town was close enough to walk to weather permitting. We did hear some noise from the street and upstairs tenants which the hosts were forthcoming about, however it was not enough to deter us from staying again. Overall, fantastic place to spend the weekend!

4.99 out of 5 average rating, 311 reviews

Treehouse in Wallkill

The Treecastle at the Roundhouse Homestead

NicoleRating, 5 stars5 days ago

The treehouse was such an amazing stay for us. Everything was clean, the host was super responsive and helpful, and the location was good too. We felt right at home staying here & will absolutely be back. I wish we could have spent more time here. The outdoor bathroom was one of my favorite parts. There was overall a peaceful atmosphere and was a great way place relax and unwind. The hosts left us some delicious homemade bread and muffins. They also included fresh honey and eggs. They put so much love and thought into every detail of the treehouse, surrounding area and even the guestbook. I highly recommend booking - you won’t regret it!!

4.9 out of 5 average rating, 231 reviews

Apartment in Philipstown

Foxglove Farm

MargaritaRating, 5 stars3 days ago

This place is absolutely stunning - even the rain can’t take away its charm. And the concierge is the smartest, friendliest cat we've ever had the pleasure of meeting!

Guesthouse in Philipstown

5 out of 5 average rating, 94 reviews

Historic 1 bedroom home in Cold Spring, NY

MiriamRating, 5 stars2 weeks ago

Pieter and Jackie were some of the loveliest hosts I have encountered and easily available by text. We stayed at their place for 3 nights over MDW and they set up chairs for us to watch the small parade. We also enjoyed using the grill and chimnea and they had firewood, starters, and marshmallows sticks for our smores. We loved the beautiful and equipped kitchen and cozy bed. The place has tons of charm and character and easy to access trailheads. Would definitely stay again!

4.9 out of 5 average rating, 30 reviews

Cottage in Putnam Valley

Hudson Valley Home 50 Min from NYC - dog friendly

EvanRating, 5 stars1 week ago

Really enjoyed our 1.5 month stay here. The place - while small - is cozy and has everything you'd need. Joanna does a great job making sure it's fully stocked (kitchen supplies, cleaning supplies, etc). The beds were comfy and the internet worked great. It's a very quiet space, in a nice little neighborhood, and the deck space is phenomenal (although it can get buggy!). We would definitely say again

4.94 out of 5 average rating, 54 reviews

Home in Cold Spring

Summer Adventures in Cold Spring at Gilbo's

BillRating, 5 stars2 weeks ago

We were there for a USMA graduation, and the location / accommodations worked great. Handy having a decent grocery store two blocks away. The walking loop down to the Foundry and Cold Springs Park is delightful. Nice with our house guests (extended family and friends) to be able to spread out in the place. Kitchen was spacious and awesome for family meals. Pool wasn't open yet, but looked inviting to add to the outside BBQ area.

4.95 out of 5 average rating, 232 reviews

Guesthouse in Mahopac

Lakeview Guesthouse with Sauna

CatherineRating, 5 starstoday

We enjoyed our overnight stay at The Lake House while visiting family in the area. Lily kept us updated and provided detailed instructions for finding her treetop home. We especially appreciated her thoughtfulness in providing extra chairs for my family, so we could enjoy a meal together. Our favorite spot was by the window in the dining room with its amazing view of the lake… so serene! Comfy bed, peaceful location close to amenities, great host, and lovely art throughout the home made this the perfect stay for us. Note: access is up a flight of stairs so the home is not for those with mobility with issues. You’d also want a good back-up camera on your vehicle for easing down the steep driveway. Otherwise, don’t hesitate to stay here.