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Vacation rentals in Montgomery

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Quick stats about vacation rentals in Montgomery

  • Total vacation rentals

    Explore 20 vacation rentals in Montgomery

  • Nightly prices starting at

    Montgomery vacation rentals start at €103 per night before taxes and fees

  • Verified guest reviews

    Over 1,090 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Montgomery vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Montgomery rentals

  • 4.9 Average rating

    Montgomery stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Montgomery

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A contemporary house is displayed, featuring a sleek exterior of wood and metal. Expansive windows offer a view of the surrounding trees. A spacious deck extends from the structure, providing a seamless transition to the outdoor environment.
Home in Accord
4.99 out of 5 average rating, 104 reviews

Accord River House

Welcome to our house in the woods! 12 acres surrounded by trees and above a series of waterfalls along the Stony Kill, which runs all the way from Minnewaska State Park through our property and into downtown Accord. You can sit in a hammock outside, soak in our hot tub while listening to the river, or chill out inside with some tunes or the TV projector. Budding entomologists will enjoy the endless procession of bugs, ants, spiders, ticks, and other creepy-crawlies that is part of River House.

Top guest favorite
A spacious living area features large glass doors that bring in natural light and provide views of the outdoors. Comfortable seating includes a modern sofa and armchair, accompanied by a coffee table and a dining area positioned nearby.
Chalet in Pine Bush
4.98 out of 5 average rating, 139 reviews

Spacious A-Frame Getaway near Hiking and Wineries

Escape to our A-frame in the heart of the Shawangunks, nestled within the picturesque Hudson Valley. Just 1.5-2 hours from NYC, our spacious and serene home is perfect for a peaceful retreat, outdoor adventures, and exploring local wineries. Nearby attractions include Lake Minnewaska Park, Mohonk Preserve, Sam’s Point, the Shawangunk Wine Trail, Ellenville and Blue Cliff Monastery. The location also provides convenient access to explore many of the Hudson Valley and Catskill towns and villages.

Top guest favorite
A soft, textured sofa in a light neutral tone is positioned against a warm, smooth wall. A single floor lamp provides gentle lighting beside a small black side table. An adjacent window is dressed with sheer curtains, allowing natural light to filter softly into the space.
Cottage in Warwick
4.99 out of 5 average rating, 135 reviews

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Top guest favorite
The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.
Cabin in Saugerties
4.99 out of 5 average rating, 156 reviews

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

Guest favorite
A charming two-story cottage is surrounded by vibrant landscaping, featuring a mix of colorful flowers. The exterior is painted in green with maroon shutters adorning the windows. A wooden staircase leads to the upper entrance, while a welcoming front door is accented by a small planter.
Guest suite in Montgomery
4.94 out of 5 average rating, 580 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

Guest favorite
An outdoor area is illuminated by a vibrant red fireplace, surrounded by cozy seating arrangements with cushions and throws. Potted flowers add color, while string lights gently glow above, enhancing the serene atmosphere of the deck. A natural stone backdrop is visible in the distance.
Cottage in Greenwood Lake
4.97 out of 5 average rating, 391 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

Top guest favorite
A spacious log cabin features a welcoming wraparound porch with wooden railings. The two-story structure boasts a combination of gabled roofs and large front windows, surrounded by lush green landscaping. A paved driveway leads up to the entrance, enhancing the environment's rustic charm.
Cabin in Pine Bush
4.89 out of 5 average rating, 233 reviews

NEW! Foley's Riverfront w/ Hot Tub-LEGO LAND CLOSE

Escape to the ultimate Hudson Valley retreat when you stay at this 4-bedroom, 3-bathroom vacation rental Log Cabin in Pine Bush! The property is situated on 6 private acres of land and boasts an extensive 3,500 square feet of rustic paradise, making it ideal for large families or groups of up to 12. Enjoy amenities such as a hot tub, game room, and home theater, which are sure to elevate your experience. Explore the numerous outdoor activities nearby as. well as the NEW LEGO LAND NEARBY!

Top guest favorite
Home in Montgomery
5.0 out of 5 average rating, 20 reviews

The B House

The “B” house, constructed in the 19th century, underwent renovations and modernizations to accommodate contemporary living standards while preserving its original architectural charm. The house boasts magnificent beams that span the entire interior, creating a sense of grandeur. Additionally, newly renovated appliances and updated bathrooms have been installed throughout the property. The kitchen features an expansive open space, elegant countertops, cooking essentials are top-notch.

Guest favorite
A modern dining area features a wooden table surrounded by stylish chairs. Five pendant lights hang above the table, providing soft illumination. A plant stands nearby, contributing to the fresh ambiance, while a sliding door offers access to outdoor space.
Cottage in Pine Bush
4.93 out of 5 average rating, 133 reviews

Modern 3BR BoHo Retreat/Nearby Hiking, Wineries

Our newly modern bohemian cottage (aka Green House!) is perfect for your next weekend getaway or a new WFH locale. Decompress from city stress in this calm, serenely appointed private home. Close to attractions but far enough away to escape, you'll never want to leave. NYC: 79 mi. Hunter Mountain Ski Resort: 60 mi. Pine Bush - groceries/supplies: 7 mi. Middletown - shopping (Walmart, Target, Best Buy, Home Depot): 16 mi. Hiking trails: 7 mi. Horseback riding: 7 mi. Sky diving: 15 mi.

Guest favorite
A modern kitchen area is presented with open wooden shelves displaying dishes, glassware, and decorative items. Below, a gas stove and black refrigerator are complemented by a light fixture and a collection of utensils, offering a functional and organized space.
Cottage in Goshen
4.92 out of 5 average rating, 381 reviews

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Picture this... You escape to a relaxing, picturesque, and peaceful country cottage and enjoy some of your favorite convenience amenities like 1 Gig Wifi and your favorite streaming sources. Just 10 minutes to LEGOLAND, 3 miles to the famous Orange Heritage Trail, and less than 20 minutes to America's oldest winery, Brotherhood, this cottage has something to offer for everyone. You'll be minutes from conveniences like Target but taking in the views, you'd never know it.

Top guest favorite
A charming farmhouse exterior is presented, featuring a well-maintained porch with seating. The facade showcases a combination of horizontal and vertical siding, complemented by a sloped roof. Lush greenery surrounds the property, enhancing the serene atmosphere of the rural setting.
Home in Kingston
4.95 out of 5 average rating, 368 reviews

Hudson Valley Hygge House~ comfort in the country!

Experience the cozy charm of hygge at the farmhouse by a tranquil pond in Rosendale. Nestled in the Hudson Valley, just minutes from Kingston, Stone Ridge, and High Falls—and only 90 miles from NYC—this retreat offers pure serenity. Located on a quiet country road, enjoy the sounds of birdsong, evening frog lullabies, and a gas fireplace for a cozy winter escape. Set on over 3 acres, nature abounds here. Come and enjoy all the Hudson Valley has to offer!

Top guest favorite
A modern living room is presented with two comfortable couches adorned with soft throws and decorative pillows. Two dark coffee tables sit centrally on a textured area rug. Large windows offer glimpses of the surrounding trees, allowing natural light to fill the space.
Chalet in Gardiner
4.97 out of 5 average rating, 343 reviews

Modern Zen Chalet at the Foot of Gunks w Mt. View

Kick back at the foot of the Shawangunk Mountains in this calm, stylish home. Surrounded by forest, the house features large picture windows in every room to help you reconnect with nature. Enjoy the natural stone porch with a fire pit and newly built barrel sauna. Located near Minnewaska State Park, with quick access to trails, and views of Millbrook Ridge and the Gunks’ iconic climbing routes right from the windows.

Popular amenities for Montgomery vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Montgomery

Top guest favorite
A striking red barn-style building is framed by lush greenery and a well-maintained stone wall. The entrance features double garage doors, complementing the rustic charm. Soft ornamental grasses and flowering plants add a touch of color to the exterior.
Barn in Montgomery
4.98 out of 5 average rating, 43 reviews

16taft

Top guest favorite
A single-story cottage is presented with a light-colored exterior and a welcoming front porch. A carport is included on one side, while a neatly maintained lawn features shrubs and trees in the background. The sky displays a mix of clouds and blue hints.
Cottage in Montgomery
5.0 out of 5 average rating, 87 reviews

The Pullman Cottage • Hudson Valley

Guest favorite
Home in Montgomery
4.86 out of 5 average rating, 7 reviews

Treehouse-Inspired Cabin Escape w/ Theatre & Gym

Guest favorite
A serene outdoor space features a crystal-clear pool surrounded by lush greenery and soft landscaping. Lounge chairs and a bright orange umbrella provide comfortable seating, while the area also includes a hot tub for relaxation. A wooded backdrop adds to the peaceful setting.
Home in Montgomery
4.94 out of 5 average rating, 82 reviews

Hudson Valley Home with Pool & Jacuzzi

Top guest favorite
Apartment in Montgomery
4.96 out of 5 average rating, 24 reviews

Cozy studio apartment with everything you need!

Top guest favorite
A spacious luxury retreat is showcased in this exterior view, featuring a modern design with a blue façade and stone accents. Large windows enhance the inviting appearance, while the landscaped yard includes manicured shrubs and a stone driveway leading to the entrance.
Home in Montgomery
5.0 out of 5 average rating, 39 reviews

Fairway Retreat - Montgomery, NY

Top guest favorite
Apartment in Montgomery
4.98 out of 5 average rating, 52 reviews

A modern oasis in the Hudson Valley and nature.

Guest favorite
A serene outdoor space features a private pool surrounded by a well-maintained garden. A koi pond with lily pads adds tranquility, while lounge chairs provide comfortable seating. Lush greenery and colorful shrubs create a peaceful atmosphere, perfect for relaxation and enjoying nature.
Home in Montgomery
4.92 out of 5 average rating, 49 reviews

Serene Hudson Valley Escape Hottub/Pool/King Suite

When is the best time to visit Montgomery?

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Frequently Asked Questions

  • What are the best places to stay in Montgomery?

    Montgomery has a mix of historic village homes, countryside cottages, and farmhouse stays. Many guests choose accommodations near the central area for walkable access to shops and dining, or in rural surroundings for extra space and views.

  • What are the best things to do in Montgomery with kids?

    Families can explore local parks, visit farm stands for seasonal treats, or attend community fairs. Trails and rivers nearby provide opportunities for outdoor play, and local shops sometimes host interactive arts or craft sessions for children.

  • What are some of the best things to do in Montgomery?

    Explore the historic village center, relax in local parks, and visit art spaces or weekend farmers’ markets. Seasonal events often highlight local crafts, music, and culinary traditions.

  • How is the weather in Montgomery?

    Montgomery has cold winters with temperatures from 16–35°F (-9–1°C) and warm, humid summers peaking near 82°F (28°C). Spring and autumn are often milder, with blooming flowers or colorful foliage and steady rainfall year-round.

  • When is the best time to visit Montgomery?

    Many visitors enjoy Montgomery in late spring through early autumn, when temperatures are milder and greenery is lush. Seasonal festivals and local markets are frequently suggested during these months for their welcoming community atmosphere.

  • What are the best places to visit in Montgomery?

    Popular places include parks along the Wallkill River, the village’s historic district, and local galleries housed in heritage buildings. Seasonal farm markets and art spaces often draw visitors interested in community life.

  • What are some hiking trails in Montgomery?

    Montgomery has several locally maintained walking and biking trails passing through woodlands, meadows, and near the Wallkill River. Nearby nature preserves also feature loop paths and gentle hikes well-suited for all ages.

  • What are some family activities we can do in Montgomery?

    Enjoy time together at local playgrounds, participate in seasonal festivals, or try hands-on art workshops often hosted in the village. Farmers’ markets, outdoor concerts, and visits to pick-your-own orchards are also frequently recommended.

  • What are some of the best day trip ideas from Montgomery?

    Day trips might include exploring regional wineries, visiting art museums, or enjoying outdoor adventures in nearby state parks. Scenic drives through the Hudson Valley landscape are also frequently suggested for visitors seeking nature and local culture.

  • Are there any pet friendly accommodations available in Montgomery?

    You will find a range of pet friendly accommodations in Montgomery, especially in residential neighborhoods and rural outskirts. Many hosts are welcoming to four-legged guests but it is helpful to confirm specific amenities in advance.

  • What are some local tips for visiting Montgomery?

    Explore the village center on foot to take in local shops, bakeries, and murals that reflect community spirit. Bringing layers is useful, as weather can shift seasonally, and many visitors enjoy checking local calendars for community events.

  • What is Montgomery known for?

    Montgomery is known for its small-town charm, historic downtown area, and scenic landscapes surrounded by farms and orchards. The village has a tradition of celebrating local arts, seasonal produce, and community events.

  • What are the best hidden gems to explore in Montgomery?

    Montgomery has locally owned antique shops, pocket parks, and art galleries tucked into historic buildings. Exploring mural-adorned alleys or trails along the riverbanks can reveal less-traveled corners and unique views.

  • What are the best foods to try in Montgomery?

    Montgomery has a tradition of farm-to-table dining, with favorites including apple cider, artisan cheeses, and handmade pastries. Local cafes and restaurants feature seasonal produce, classic American dishes, and regional treats.

  • What should I bring for a trip to Montgomery?

    Pack clothing layers for shifting temperatures, a rain jacket, and comfortable walking shoes for exploring parks and the village center. Sunscreen, reusable water bottles, and a camera are frequently suggested for outdoor activities and sights.

  • What is the nightlife in Montgomery like?

    Montgomery has relaxed nightlife centered around laid-back pubs, wine bars, and venues with live music or open mic evenings. Locally owned taverns in the village center provide a social atmosphere for both residents and visitors.

  • What are the most popular events or festivals in Montgomery?

    Montgomery’s calendar frequently features community fairs, harvest festivals in autumn, and parades during major holidays. Art shows and seasonal markets, often held in the village center, are known for celebrating local talent.

  • Are there family friendly vacation rentals in Montgomery?

    Montgomery features family friendly vacation rentals ranging from historic homes in the village center to country cottages with open spaces. Hosts frequently provide amenities like kitchens, extra bedding, and outdoor areas.

Destinations to explore