Montgomery holiday lettings

We found 120 holiday rentals — enter your dates for availability

Discover a selection of 11 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.

Holiday rentals with weekly discounts - Montgomery

Showing deals for:13 Mar - 20 Mar

Image gallery for Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Private kitchen
9.8 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen, NY

8% off
Price is £1,029
for 7 nights, 1 cottage
£147 per night
includes taxes & fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Find spaces that suit your style

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)
  • 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)
  • SplashDown Beach (17.2 mi / 27.7 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)
  • Storm King Art Center (11.6 mi / 18.7 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)

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 best area to stay is the charming village of Montgomery itself. This picturesque neighbourhood offers a delightful blend of historic charm and modern conveniences, making it an ideal base for your holiday. With a variety of holiday rental options available, ranging from cosy cottages to spacious homes, you'll find something to suit your preferences.

The village is particularly known for its stunning historic architecture, with many buildings dating back to the 19th century. A visit to the Montgomery Village Hall, a beautiful example of Gothic Revival architecture, is a must. Additionally, the nearby Montgomery Park provides a lovely setting for leisurely strolls or picnics, showcasing the area's natural beauty.

Another appealing aspect of Montgomery is its proximity to the scenic Hudson Valley, great for those who wish to explore the outdoors. You can embark on hikes or enjoy activities at the nearby Wallkill River, which offers opportunities for kayaking and fishing. The region is also renowned for its wineries and farms, making it a great destination for those interested in local produce and wine tasting.
How much does it cost to rent a holiday home in Montgomery?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Montgomery to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Montgomery holiday house rentals?
You can find great discounts on house rentals in Montgomery on Vrbo, 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.
Where are the best Montgomery ski resort rentals?
For ski resort rentals near Montgomery, New York, travellers should explore the nearby areas of the Hudson Valley, particularly the towns of New Paltz and Kingston, which are within a reasonable driving distance to the ski resorts. New Paltz offers a selection of charming cabins and lodges located in the picturesque landscape, often featuring amenities such as fireplaces, fully equipped kitchens, and outdoor spaces for relaxation. Many properties also provide easy access to hiking trails in the nearby Shawangunk Mountains, superb for outdoor enthusiasts.

In Kingston, visitors can find a range of accommodations, from modern apartments to historic homes, many of which have been updated with contemporary amenities while retaining their vintage charm. These properties typically include open living areas, private bathrooms, and some even offer access to communal amenities like pools or fitness centres. Travellers will appreciate the close proximity to local restaurants, coffee shops, and shops that enhance the overall experience.
What is the most popular type of holiday rental accomodation in Montgomery?
In Montgomery, holiday houses are the most popular type of rental, with around 10 available in the area. These properties typically offer spacious interiors, multiple bedrooms, fully equipped kitchens, and often feature outdoor spaces like gardens or patios, ideal for enjoying the fresh air and surrounding views. Additionally, there are several apartments and cabins scattered throughout the town, providing alternative options for travellers seeking a more compact or rustic experience.
Are there any family house rentals in Montgomery?
In Montgomery, New York, there are several family-friendly house rentals available, making it an appealing choice for groups seeking a comfortable getaway. The area features spacious homes with amenities such as large living rooms, fully equipped kitchens for preparing family meals, and outdoor spaces for children to enjoy.
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, making it a delightful choice for travellers seeking relaxation and leisure. The area is known for its picturesque landscapes and charming small-town atmosphere, providing a serene backdrop for a getaway. Many of these properties come with amenities such as private swimming pools, outdoor hot tubs, spacious decks, and fully equipped kitchens, allowing for both comfort and convenience during your stay.
Can I find long-stay holiday rentals in Montgomery?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Montgomery?
In Montgomery, New York, there are several pet-friendly house rentals available, ideal for those travelling with furry companions. The area offers a variety of holiday homes that typically feature amenities such as spacious yards, fully equipped kitchens, and comfortable living spaces. Many properties also come with outdoor areas, great for pets to enjoy the fresh air.
Are there any remote work holiday rentals in Montgomery?
In Montgomery, New York, there are several remote work holiday rentals available, with around 13 options for those seeking a conducive environment for productivity. Many of these properties are equipped with essential amenities such as Wi-Fi, dedicated desk spaces, and comfortable chairs designed for long hours of work. Travellers can expect a variety of settings, from charming cottages to spacious homes, often featuring peaceful surroundings that enhance focus and creativity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Montgomery holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
What are popular rental amenities in Montgomery?
In Montgomery, holiday rentals typically feature a range of desirable amenities that cater to the needs of travellers. Most properties are equipped with a kitchen, allowing guests to prepare their own meals, which is especially convenient for families or those planning longer stays. Additionally, many rentals include modern appliances such as dishwashers, microwaves, and ovens, making meal preparation and clean-up straightforward. Stovetops are also commonly available, providing guests with the flexibility to cook as they would at home.
When is the best time to visit Montgomery for a holiday rental?
July is the most popular month to visit Montgomery, New York, attracting a multitude of holidaymakers eager to enjoy the vibrant summer atmosphere. The peak season runs from June to August, when the warm weather creates an inviting environment for outdoor activities, charming local festivals, and leisurely exploration of scenic parks and historic sites.

During this time, temperatures typically hover in the mid-20s Celsius, providing a superb backdrop for activities like hiking, picnicking, and enjoying the local cuisine at outdoor eateries. Whether you're wandering through the picturesque streets or partaking in summer events, Montgomery buzzes with energy and offers a delightful experience for visitors.

If you're looking for a more budget-friendly option, consider planning your trip in December. While this month sees fewer tourists, it offers a unique charm with festive decorations and a quieter atmosphere. Embrace the holiday spirit and take in the serene landscape, superb for reflective walks and cosy evenings.
How early should I book a Montgomery holiday rental?
Book your Montgomery holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Montgomery?
In Montgomery, New York, visitors can explore several charming attractions. The historic district boasts beautiful 19th-century architecture and is home to the Montgomery Village Hall, which reflects the town's rich history. The nearby Orange County Farmers Museum offers insights into the agricultural heritage of the region and features various exhibits and events throughout the year.

For those who enjoy nature, the scenic Wallkill River provides opportunities for outdoor activities such as fishing and kayaking, while the expansive Montgomery Park offers picnic areas, walking trails, and playgrounds for families.
Can I change or cancel my Montgomery home rental booking on Vrbo?
To find Montgomery holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Montgomery holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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