Montgomery holiday rentals

We found 122 holiday rentals — enter your dates for availability
Discover a selection of 14 homes and other holiday rentals in Montgomery that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the best amenities for spending time at your home away from home, which might include cable TV and a washer and dryer. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

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The friendly area of Montgomery awaits your stay

The gardens and surrounding scenery provide a peaceful ambience to your holiday home in Montgomery. This welcoming and trendy city entices travellers with its shopping and restaurants. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Montgomery

Are you hoping to find attractions to visit during your stay? Venture out of your cosy holiday rental and experience everything that makes Montgomery a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Ice Time Sports Complex (6.7 mi / 10.8 km)
  • Brotherhood Winery (7.6 mi / 12.3 km)
  • Goshen Historic Track (9.7 mi / 15.6 km)
  • LEGOLAND® New York (11.2 mi / 18 km)
  • Robibero Winery (13.5 mi / 21.7 km)
  • Benmarl Vineyards and Winery (13.9 mi / 22.4 km)

Exploring the natural landscape of Montgomery

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Montgomery is a great spot to appreciate mother nature. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Algonquin Park (9.3 mi / 14.9 km)
  • Sam's Point Preserve (12 mi / 19.3 km)
  • The Rock Sports Complex (12.8 mi / 20.5 km)
  • Lake Minnewaska Beach (13.8 mi / 22.2 km)
  • Shawangunk Mountains (14 mi / 22.5 km)
  • Minnewaska State Park (14.3 mi / 23.1 km)

How to get to and around Montgomery

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 8 mi (12.9 km) from the city centre.

Frequently asked questions

What is the best area to stay in Montgomery when booking a holiday rental?
When considering a holiday rental in Montgomery, New York, the Montgomery village area is an excellent choice. This quaint village offers a charming atmosphere with a variety of properties available, ranging from cosy cottages to spacious family homes, providing ample options for different group sizes and preferences.Staying in the village allows easy access to local attractions such as the historic Montgomery Village Hall and the serene Wallkill River National Wildlife Refuge, where visitors can enjoy nature walks and birdwatching. The area is also known for its friendly community vibe and local eateries, making it an ideal base for exploring the rich history and natural beauty of the Hudson Valley.For those interested in a more rural setting, the outskirts of Montgomery offer a peaceful retreat while still being close enough to enjoy the village's amenities.
Where are the best Montgomery ski resort rentals?
For those looking for ski resort rentals near Montgomery, New York, the closest major ski area is located a short drive away in the nearby Catskill Mountains, particularly around areas like Hunter and Windham. In Hunter, visitors can find a variety of rental options, including condos and lodges that cater to different group sizes. Many of these properties come equipped with amenities such as hot tubs, fireplaces, and fully stocked kitchens, which are superb for unwinding after a day on the slopes.In the charming town of Windham, you'll discover a selection of quaint cabins and modern chalets. These often feature spacious living areas, outdoor decks, and sometimes even stunning mountain views. Many rentals in this area also provide easy access to local shops and dining options, enhancing the overall convenience for travellers.Additionally, the surrounding region is known for its picturesque landscapes and opportunities for winter activities beyond skiing, such as snowshoeing and sledding. Rentals situated near the ski resorts often highlight these amenities, along with proximity to scenic hiking trails that can be enjoyed during the off-season.
What is the most popular type of holiday rental accomodation in Montgomery?
In Montgomery, holiday houses are the most popular holiday rental option, with approximately 44 available throughout the area. These homes typically offer spacious interiors, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as gardens or patios—ideal for families or larger groups looking to enjoy a relaxing stay. Additionally, there are about 12 apartments, which provide a more compact living space, often featuring modern amenities and convenient locations near local attractions. For those seeking a rustic experience, several cabins can also be found, offering a unique getaway amidst nature.
Are there any family house rentals in Montgomery?
In Montgomery, New York, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The area features spacious homes with amenities such as generous living rooms, fully equipped kitchens for preparing family meals, and outdoor spaces for kids to play.Visitors can explore nearby attractions like the scenic Montgomery Park, which offers playgrounds and picnic areas, great for a family day out. The town's historic charm is complemented by local shops and restaurants, providing a warm and inviting atmosphere for families.
Can I rent a holiday home with a pool or hot tub in Montgomery?
In Montgomery, New York, there are several holiday homes available for rent that feature pools and hot tubs. This charming town offers a mix of rural tranquillity and access to local attractions, making it an appealing choice for travellers seeking a relaxing getaway. Many of the available rentals come with amenities such as private swimming pools, outdoor hot tubs, and spacious patios, superb for enjoying the beautiful surroundings. Additionally, fully equipped kitchens and comfortable living spaces are common, allowing for a homely atmosphere while you unwind.
Are there pet-friendly house rentals in Montgomery?
In Montgomery, New York, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these properties come equipped with amenities such as spacious backyards, fully stocked kitchens, and comfortable living areas, making them ideal for families or groups.The area itself offers a charming small-town atmosphere, with local parks nearby where pets can enjoy some outdoor time. Additionally, the scenic Hudson Valley region surrounding Montgomery features various walking trails and nature spots, great for leisurely strolls with your furry companions.
Are there any remote work holiday rentals in Montgomery?
In Montgomery, New York, there are numerous remote work holiday rentals available, with around 56 options to choose from. This charming town offers a blend of historical charm and modern conveniences, making it an excellent choice for those looking to work remotely. Many of the properties come equipped with essential amenities for remote work, such as high-speed internet, dedicated workspaces with desks and chairs, and free Wi-Fi access.Travellers can expect comfortable living spaces that allow for both productivity and relaxation, often featuring fully equipped kitchens for preparing meals and outdoor areas to unwind after a day of work. The town's proximity to local shops, parks, and recreational activities adds to the appeal, providing opportunities for breaks and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Montgomery?
In Montgomery, popular holiday rental amenities include kitchens, which allow guests to prepare their own meals, and desks that provide a convenient workspace for those needing to catch up on tasks. Many rentals also feature coffee and tea makers, great for a morning pick-me-up. A fireplace is a sought-after amenity, adding warmth and a cosy atmosphere during colder months. Additionally, some properties are located near golf courses, making it easy for enthusiasts to indulge in a round of golf.
When is the best time to visit Montgomery for a holiday rental?
The best time to visit Montgomery for a holiday rental is during the peak season, which spans from June to August. This vibrant period draws families and travellers looking to enjoy outdoor activities, local festivals, and the lush scenery that New York has to offer. July, in particular, stands out as the most popular month, where you can immerse yourself in the lively option and engage in various summer events.During these summer months, you can expect pleasantly warm temperatures, typically ranging from 20 to 30 degrees Celsius, great for exploring Montgomery's parks and historic sites. The region is alive with outdoor opportunities, from hiking scenic trails to enjoying leisurely strolls along the scenic Hudson River.For those seeking a more economical experience, consider planning your visit in December. This winter month showcases a tranquil side of Montgomery, offering a chance to enjoy the festive decorations and a quieter pace. It's a wonderful time for cosy indoor activities, like visiting local shops and enjoying the charm of the town without the crowds.
What are the top attractions in Montgomery?
In Montgomery, New York, visitors can enjoy a range of attractions that highlight the area's historical and natural beauty. The historic district features charming 19th-century architecture, and a stroll through the streets allows guests to appreciate the quaint atmosphere. The Montgomery Village Park is a lovely spot for outdoor activities, with playgrounds and picnic areas, superb for families.Nearby, the Wallkill River provides opportunities for kayaking and fishing, making it a great place for nature enthusiasts. The nearby Orange County Arboretum is a must-visit for those interested in horticulture, showcasing a diverse array of plants and beautiful walking paths. Additionally, the area hosts various seasonal events, including farmers' markets and community festivals, which offer a taste of local culture and produce.
Are all fees included in the Montgomery holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Montgomery holiday homes with parking?
Stayz offers a wide selection of holiday homes in Montgomery with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Montgomery holiday homes?
You can find great discounts on holiday homes in Montgomery on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Montgomery holiday home booking on Stayz?
To find Montgomery holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Montgomery?
A long-stay holiday home in Montgomery is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Montgomery holiday home?
Book your Montgomery holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Montgomery?
Prices for holiday homes in Montgomery vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Montgomery to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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