Vacation rentals in Montgomery

4.88 out of 5 average rating, 146 reviews

A covered front porch features a pair of vintage rocking chairs in soft turquoise, set against a backdrop of pale yellow siding. The porch floor exhibits natural wear, enhancing its rustic charm. Large windows with dark shutters allow natural light to fill the space.

Home in Pine Bush

Charming Revitalized 1920s Country Style Home

Venture back in time in this tastefully appointed historical residence. First floor apartment is a quaint abode showcasing boutique furnishings and decor, contrasting textures and motifs, arched doorways, a covered front porch, and a walkout to the backyard. We are 20 minutes away from Legoland, also located near Wallkill, and an easy drive to Warwick and Patterson. Our home is eclectic and unique, placed in the historic district of pine bush. This home provides up to date appliances and cozy furnishings while still holding onto that good ol’ 1920’s feel. Plenty of room for dining in and an easy ride or walk to great food. This home is bright and cheery yet provides privacy and warmth. The entire first floor is your domain. With a private entrance and easy parking. The locked doors you will encounter is for your privacy. There are permanent renters above you, however they have their own entrance and are completely separate. Trust us you won’t need more space than what’s provided, very roomy with a closet in each room, as well as in the dining area. Up until your check in we are available to you through Airbnb with any questions or concerns you might have. After check in most vacationers prefer to hit the ground running and begin enjoying their stay, however for little bumps in the road a number will be provided in order to continue taking care of you. The property boasts easy access to hikes, Wallkill Farms, wineries, Legoland and is walking distance from multiple restaurants, antique shops, and more. We recommend renting a car. While this home is walking distance to restaurants and downtown pine bush the beautiful rural scenery means a little distance of 10-20 minutes of driving between wineries and hikes and other enjoyable activities. We want our guests to enjoy their time to the fullest, and know that we care about their stay. Which is why we like to make clear our home runs on city water. There is an initial aroma from the faucet, however it doesn’t last long and adjustments to that are in the process. We of course offer you filtered water for you and your family. This home is multiple stories which adds to its beautiful character. You and your family will be occupying the entire first floor. The upper level has permanent renters, however they have a separate entrance and are quiet, as well as accommodating.

4.96 out of 5 average rating, 263 reviews

Tiny home in Montgomery

Lux Cabin on Farm, River, Animals, Smart Projector

Take a break from your day to day and enjoy this serene and unique escape. The Trek is a custom built and designed cabin nestled in the heart of the Hudson Valley! It is a high class, off-the-grid experience. Come experience the escape for your self - Watch a movie, visit the animals on the farm, read a book, roast s’mores or enjoy a night under the stars around the fire pit, how ever you like to relax do it at The Trek. Located just 3 Minutes from cafes, local restaurants, hikes and much more.

Guest suite in Montgomery

4.95 out of 5 average rating, 490 reviews

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

4.97 out of 5 average rating, 336 reviews

A rustic cabin is enveloped by lush greenery, showcasing ivy climbing its wooden exterior. The structure features two windows and a stone feature in the front yard, which is bordered by wild grass, enhancing the connection to the surrounding evergreen forest.

Cabin in Wurtsboro

Spring Spa on a Cascading Brook - The Water House

The brook flows through an evergreen forest creating a nourishing environment and the perfect setting for a relaxing and rejuvenating spa retreat. The living/dining room, hot tub/deck, and gas fire pit are set overlooking the cascading brook, ideal for entertaining, meditating or simply as an enjoyable natural muse. The soft, cozy and elegantly vintage styled interior is illuminated and warmed with central heating, ambient lighting and a home surround sound entertainment system with karaoke.

4.99 out of 5 average rating, 300 reviews

A tiny house with large windows is nestled among the trees, offering a secluded retreat. A wooden deck with stairs leads to the entrance. An outdoor dining space with an umbrella and a propane grill is visible alongside a gravel area, complemented by a playful dog on the lawn.

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, 25 reviews

The open floor plan reveals a spacious living area with comfortable seating, including a sofa and armchair, surrounding a round wooden coffee table. Natural light floods in through multiple windows, and a well-equipped kitchen is visible in the background, featuring wooden cabinetry and modern appliances.

Apartment in Montgomery

Apt 201 · Hudson Valley Luxury Apartment!

Large Brand New Apartment on Clinton St in Montgomery. 1 Bedroom, sleeps 4. King bed, 2 Twin fold-ups, fantastic eat in kitchen, Stainless and quartz, 65 inch Smart TV and tons of storage. Kitchen fully stocked for an easy stay with cooking utensils and everything needed for entertaining. Super fast Wifi and a nice work space. Plenty of dining, coffee and shopping with easy walking. Enjoy the Village of Montgomery. Close to Angry Orchard, Legoland, Bethel branches and nearby wedding venues.

4.9 out of 5 average rating, 162 reviews

The kitchen features a modern design with a sleek countertop and open shelving. Glassware and ceramic dishes are neatly arranged on the shelves, while the cooking area is equipped with a stovetop. Soft lighting enhances the welcoming atmosphere of the space.

Cottage in Gardiner

Little Cottage Under the Ridge

Visit the cottage for an upscale retreat in the rock climbing epicenter of New York’s famous Shawangunk ridge. our mountain top paradise sits on a dead end road amongst untouched nature, only minutes to town, with a small chef’s kitchen, breakfast bar, and brand new everything. As the last property before Minnewaska’s protected preserve land, the cottage offers unmatched peace and quiet. Enjoy a private campfire beneath mature maple & oak trees that decorate our secluded five acre property.

4.92 out of 5 average rating, 266 reviews

A functional kitchen area is equipped with modern appliances, including a refrigerator and a microwave. Open shelving presents glassware and kitchen items, while a white tiled backsplash complements the wooden countertop. Natural light enters through the window above the sink, enhancing the space.

Cottage in Goshen

Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND

When you're looking to get away from it all and experience some peace and quiet surrounded in nature, this Cottage fits the bill. Whether it's enjoying fireflies over the field at dusk or enjoying cheerful birds in the morning, this beautiful Cottage sets the stage for you to be refreshed and renewed by the time you check out. While it feels like a secluded oasis, this place is also 10 minutes from LEGOLAND, Target, and all your other favorite conveniences. We look forward to hosting you.

4.96 out of 5 average rating, 320 reviews

A spacious bathroom is showcased, featuring a claw foot tub with an elegant chrome faucet. A modern glass shower enclosure is visible, along with a wooden vanity and mirror. The floor displays a patterned tile design, and the walls are painted in calming shades of blue.

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

A panoramic view of rolling hills and dense forests is captured at dawn, with soft mist lingering above the treetops. The sky transitions from pale pink to light blue, creating a serene atmosphere that enhances the natural beauty of the landscape.

4.98 out of 5 average rating, 379 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.

4.86 out of 5 average rating, 190 reviews

A classic white fireplace with ornate detailing is highlighted in the foreground. In the background, a doorway leads to a bright, white space, suggesting a clean and modern bathroom area. A decorative rug adds warmth beneath the fireplace.

Apartment 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!

4.96 out of 5 average rating, 108 reviews

A serene lakeside view captures a vibrant sunset, with hues of orange and pink reflecting off the calm water surface. The sky showcases a gradual transition of colors, framed by the dark outlines of distant trees at the horizon.

Cottage in Walden

Cute, Cozy, Lakefront cottage

Cute, cozy lakefront cottage on private lake. Deck with an unobstructed view of the lake. Stunning sunrises, pinewood floors in bedroom/living room/kitchen. Queen size bed in bedroom. Situated on the same lot as owner occupied main house. Quiet, residential area. Near wineries, breweries, hiking. WIFI. No TV. Unfortunately, due to severe pet allergies I am unable to host any kind of animals including emotional support and service dogs and cats of any kind.

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Other great vacation rentals in Montgomery

4.91 out of 5 average rating, 47 reviews

A compact kitchen area is equipped with essential appliances, including a white stove and refrigerator. Light-colored cabinetry provides ample storage. A cozy sofa is positioned nearby, with a decorative rug underfoot. A window allows natural light to brighten the space, enhancing functionality.

Home in Newburgh

Welcome to Newburgh's Cozy Cove

BrianRating, 5 stars2 weeks ago

This was a cute cozy cottage, just right for 3 people. This house was perfect for our quick getaway. Close to all local restaurants and store, but far enough away from all the busy roads. Owners were very friendly and helpful. Very quick to respond when we needed something. Would recommend to others.

4.97 out of 5 average rating, 34 reviews

The eat-in kitchen showcases exposed wooden beams overhead and features a farmhouse table that seats six. A blue hutch adds a touch of color, while a large window offers natural light and views of the outdoors. The space is designed to be functional and inviting.

Cottage in Wallkill

1780's Story Book Farmhouse | Winery Adjacent

JillianRating, 5 stars1 month ago

This a true, traditional and charming farm house! Brynn was very accommodating with our stay, not only did she allow both of our dogs to tag along on our weekend getaway, she also offered an early check-in and late check-out without even having to asking for one. That never happens! While this location is rather remote (which we wanted), the winery across the street is quite enjoyable, and the farmhouse is only a quick, 20 minute drive to Beacon. We also found a new favorite restaurant in HV called 'One With Land' - So worth the trip. Overall, a very pleasant stay.

4.97 out of 5 average rating, 72 reviews

A welcoming living area displays a warm leather sofa and a glass coffee table. A stylish hammock chair hangs nearby, while a fireplace with a stone surround serves as a focal point. Natural light filters through sheer curtains, enhancing the cozy ambiance.

Cottage in Middletown

⌂ Backyard Porch ⌂ Cozy Getaway ⌂ Catskills Hikes

Adryanna IlysseRating, 5 stars3 months ago

This charming cottage in Upstate NY is the perfect escape from city life. Surrounded by towering trees and nature’s tranquility, it offers a cozy, welcoming retreat. Inside, the rustic decor, soft lighting, and warm bed create the ultimate cozy atmosphere. The well-equipped kitchen and plush bed ensure comfort, making it easy to relax. The outdoor space is a highlight—sip coffee on the porch, stargaze , or explore nearby hiking trails. Whether you’re a couple, solo traveler, or small family, this peaceful retreat is a must-visit. Highly recommended!

4.87 out of 5 average rating, 46 reviews

The exterior of a black A-frame cabin is set against a backdrop of lush greenery. A spacious deck features two white chairs and ambient string lights, creating a cozy outdoor space. The surrounding trees enhance the natural, tranquil atmosphere.

Cabin in Kerhonkson

Black A-Frame: Catskills Cabin

AnatolyRating, 5 stars3 weeks ago

Amazing place in a very peaceful area! Very cozy and charming. Erica was very friendly and provided us with everything we could possibly need, as well as a very detailed guide for the local experience.

4.95 out of 5 average rating, 42 reviews

A well-lit deck overlooks the lake, surrounded by trees. A fire pit with four blue chairs is positioned nearby, adding a cozy ambiance. Twinkling string lights are visible on the railing, while the night sky showcases stars, enhancing the tranquil setting.

Home in Pine Bush

Cabin96-Shawangunk Mountain View

SamRating, 5 stars3 weeks ago

Simon & Stella were wonderful, the place was gorgeous, spotless, and had everything provided like a luxury hotel stay. The property is beautiful and peaceful, the pond has local wildlife, the grass beautiful, the view... Was an honest recharge just to hang out there, go nowhere, do nothing. Very cozy place, new, modern, quality furnishings, the pictures honestly don't do it justice. thanks so much Simon & Stella ❤️❤️❤️

4.92 out of 5 average rating, 24 reviews

A decorative shelf displays a small white planter with a green succulent, alongside a fragrance spray bottle. A vintage Lake Tahoe poster hangs above, featuring a mountainous landscape with a silhouette of a moose. Roll toilet paper is neatly arranged on the other shelf.

Home in Walden

The Gîte - Hudson Valley Retreat

DAVIDRating, 5 stars4 weeks ago

We had a wonderful stay at Roxanne's comfortable and modern duplex. The space was well-maintained and had everything we needed. Roxanne was also very responsive and friendly. My family and I came to visit the nearby Bethel facilities, and this location was perfect—right between Wallkill, Patterson, and Warwick, making it easy to visit all three. We loved the peaceful atmosphere and updated decor in the home. If you're visiting Bethel or the Hudson Valley, this is an ideal place to stay. We’d definitely return and highly recommend it!

4.97 out of 5 average rating, 61 reviews

A modern gas fireplace is featured, with flames flickering against a backdrop of stacked logs. The fireplace is enclosed in a sleek metal mesh screen, adding a contemporary touch to the cozy ambiance of the space.

Cottage in Newburgh

Lakefront Getaway 1 Hr from NYC

Zeke & KrisRating, 5 stars1 month ago

I stayed for a month solo to focus on my projects & it was the most peaceful month. The house is contained in nature with a plethora of birds & animal life that I witnessed.. a crane fishing at the creek beside the house as I worked, a pair of woodpeckers hunting at the lawn, a chipmunk that lives under the house & has a morning ritual of its own. All while the lake boasted breathtaking sunsets. On the practical side, the kitchen was fully equipped with everything one needs to cook everyday, which I did. It was private & safe for a solo girl like me to stay a month. Amazon found its way to it no problem. And there are nice streets to take long walks which I did 1 hour a day. Very friendly neighbors, everyone waves at ya. The covered patio, working from the dinner table, waking up in the bedroom to the lake.. all main areas are flanked by beauty. Really was perfect for a solo getaway. Also wifi was very reliable. Keep in mind lake living = insects. They’re harmless. Highly rec renting!