Holiday houses in Fort Montgomery

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Top-rated holiday rentals in Fort Montgomery

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Guest favourite

Cottage in Cortlandt

5.0 out of 5 average rating, 104 reviews

Cottage at Peekskill Hollow

Romantic Hudson Valley cottage just 1 hour outside NYC in northern Westchester! Beautiful, wooded location along the Peekskill Hollow Creek - just off the beaten path. You’ll be surrounded by nature and still be a hop, skip and jump away from restaurants, shopping, hiking/bike trails, West Point, the Hollow Brook Golf Club and historic sites (Revolutionary War, Rockefeller, Roosevelt, Underground Railroad). Quick access (by car or train) to/from NYC and greater Hudson Valley. High speed WiFi.

11–18 Jan

$464 NZD per night

Guest favourite

Cottage in Cortlandt

4.99 out of 5 average rating, 159 reviews

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

27 Sep – 4 Oct

$242 NZD per night

Guest favourite

Apartment in Philipstown

4.88 out of 5 average rating, 187 reviews

Foxglove Farm

Peace and tranquility await you at the end of this private road surrounded by forest. My home is a log cabin with a private apartment on the lower level, which includes a patio as well as use of other outdoor spaces. There is a fire pit just past your patio and a short path will put you on the Appalachian Trail. As an herbalist and ethnobotanist, plants are my love and my livelihood. They are an integral part of my life and my home. I welcome you to stroll through the many gardens and paths.

24 Sep – 1 Oct

$239 NZD per night

Guest favourite

Guest suite in Chester

4.95 out of 5 average rating, 230 reviews

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, and 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, a French door shower, and a kitchenette with sunny breakfast nook. It is 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.

31 Jan – 7 Feb

$196 NZD per night

Guest favourite

Apartment in Peekskill

4.84 out of 5 average rating, 115 reviews

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.

18–25 Jan

$247 NZD per night

Guest favourite

Apartment in New Windsor

4.95 out of 5 average rating, 112 reviews

Private/Spacious Studio. Guest Loyalty Program

LOYALTY PROGRAM for repeat bookings. $30 off of your second night stay ((dbl occ rates and extra guest fees apply) OR a 3rd guest stays free with your one night stay. Discount will be applied upon your inquiry. - Perfect location for your West Point visit. - SKAC -Woodbury Common Sleeps up to six guests comfortably. Safe/secure - Perfect for single travelers Parking at door for several vehicles Coffee/Tea/Keurig Close to restaurants, NYS Thruway, Routes 9W

3–10 Nov

$217 NZD per night

Guest favourite

Home in Highland Falls

4.99 out of 5 average rating, 141 reviews

Spacious, bright 5 bedroom house near West Point

Newly renovated 5 bedroom house located 4.3 miles from the Thayer Gate at historic West Point Military Academy. Located in the scenic Hudson Valley near hiking, fishing, Bear Mountain State Park and many historic sites.Woodbury Commons premium outlets are 20 minute drive. The house is comfortable with many upgrades- full oven and microwave, large fridge/freezer, USB ports .Come and see an Army game - and relax here afterwards!

27 Jul – 3 Aug

$754 NZD per night

Guest favourite

Guest suite in Haverstraw

4.95 out of 5 average rating, 293 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:)

18–25 Apr

$146 NZD per night

Guest favourite

Guesthouse in Mahopac

4.96 out of 5 average rating, 110 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac. Walkable to swimming/paddleboarding; skating/ice fishing. Many fine restaurants or casual takeout options, and boasting an excellent coffee shop. Train ride from Grand Central to Croton Falls, then a 12 minute drive or shuttle ride. Close to Fahenstock Park, Cold Springs, Beacon, Ridgefield,or walk up the hill to the trails of Volz park

28 Oct – 4 Nov

$222 NZD per night

Guest favourite

Loft in Cornwall

4.86 out of 5 average rating, 393 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside 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 flat screen Roku TV with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have their own parking space, a private first-floor entrance, full bathroom, patio, BBQ and fire pit!

24–31 Oct

$171 NZD per night

Guest favourite

Guesthouse in Peekskill

4.94 out of 5 average rating, 206 reviews

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

28 Oct – 4 Nov

$242 NZD per night

Guest favourite

Farm stay in Fort Montgomery

4.97 out of 5 average rating, 149 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.

26 Aug – 2 Sep

$453 NZD per night