Holiday rentals in Montgomery
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Quick stats about holiday rentals in Montgomery
Total holiday rentals
Explore 20 holiday rentals in Montgomery
Nightly prices starting at
Montgomery holiday rentals start at £89 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
Wifi availability
20 of Montgomery holiday rentals include wifi 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 holiday rentals in Montgomery
Guests agree: these stays are highly rated for location, cleanliness and more.
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.
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.
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.
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
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.
Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.
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
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!
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.
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.
Hidden cabin on 2 wooded acres
Retreat to a beautiful cabin and get lost on two wooded acres. Reconnect with nature in your own way - hike around nearby Lake Minnewaska, or another of the dozens of incredible trails in the area. Explore infinity under a blanket of stars and share stories gathered around the firepit. When you’re called inside, grab a book and settle in by the fireplace. Then cook a meal in our well-equipped kitchen or on the grill, and enjoy it on the patio overlooking the property.
Catskills Cabin, Hot Tub, Wood Stove, King Bed
Welcome to Minnewaska Cabin. A Catskills mountain cabin on a private forested lot, with a hot tub, a wood stove and king bed. The house is very new (completed Dec 2023) and located about 2 hours from NYC, close to many local attractions, like hiking trails, skiing and water sports. 20 mins from Minnewaska State park 35 mins from Legoland Goshen 20 mins from Resorts World Catskills casino 5 Mins from North East Off Road Adventures
Popular amenities for Montgomery holiday rentals
Other great holiday rentals in Montgomery
Cozy studio apartment with everything you need!
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Treehouse-Inspired Cabin Escape w/ Theatre & Gym
Serene Hudson Valley Escape Hottub/Pool/King Suite
16taft
The Pullman Cottage NYC Escape • Dogs Stay Free
The B House
When is the best time to visit Montgomery?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £100 | £100 | £100 | £99 | £114 | £114 | £113 | £127 | £123 | £125 | £109 | £109 |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
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.
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- Hunter Mountain
- Mountain Creek Resort
- Bushkill Falls
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Bear Mountain State Park
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Delaware Water Gap National Recreation Area
- Resorts World Catskills
- Brotherhood, America's Oldest Winery
- Hunter Mountain Resort
- Kent Falls State Park
- Mohonk Preserve
- Storm King Art Center
- Mount Peter Ski Area
- Wawayanda State Park
- Storm King Art Center
- Paterson Great Falls National Historical Park
- Peekamoose Blue Hole
- Millbrook Vineyards & Winery
- Harriman State Park
- Benmarl Winery
- Warwick Valley Winery & Distillery