Montgomery holiday rentals

We found 44 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Montgomery that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for spending time at your holiday home, which might include a garden and Wi-Fi. You're sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

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Why visit Montgomery

  • Urban parks and nature: Discover verdant parks and serene nature reserves perfect for leisurely strolls and outdoor adventures.
  • Cultural charm: Enjoy the historic village atmosphere and romantic allure of downtown Montgomery.
  • Family-friendly escapes: Experience a variety of attractions suitable for all ages in this welcoming city.
  • Eco-conscious experiences: Engage in sustainable activities and explore scenic landmarks within the city.
  • Local vibrancy: Immerse yourself in the blend of urban energy and quaint village charm.

Popular types of accommodation in Montgomery

Discover Montgomery, Massachusetts, where unique holiday experiences await. Enjoy historic attractions, scenic landmarks, and local charm while staying in Private Holiday Homes, Apartments, and Cottages. Whether you're seeking house rentals, hotel amenities, or a private patio to relax, Montgomery offers a welcoming profile for every traveller. Explore local experiences and make your visit memorable in this captivating city.

  • Private Holiday Homes: The most favoured choice, offering independent living spaces for an immersive Montgomery experience.
  • Apartments: The second preferred option, ideal for those seeking cosy, self-contained urban living.
  • Cottages: The third selection, perfect for a quaint and tranquil retreat in the countryside.
  • Cabins: The fourth choice, providing a rustic escape with a touch of nature.
  • Chalets: The fifth option, offering a stylish blend of comfort and mountain charm.**

Top attractions in and around Montgomery

Montgomery, Massachusetts, offers a delightful blend of urban parks, serene nature reserves, and inviting libraries, making it an ideal destination for romantic, cultural, and entertainment-themed holidays. Visitors can enjoy outdoor, family-friendly, and eco-conscious experiences in this charming city, which promises a variety of attractions and scenic spots to explore, ensuring a memorable and enriching holiday experience.

  • Grace Hall Memorial Library: Nestled in Montgomery, this library offers a warm family and cultural atmosphere, perfect for leisurely afternoons immersed in literature.
  • General Wareham Park: Located 11km away, this urban park provides city and family vibes, ideal for a refreshing outdoor stroll amidst urban charm.
  • Littleville Lake: Situated 8km from Montgomery, this scenic lake offers a romantic beach setting, inviting visitors to enjoy its outdoor splendour.

Things to do recommended for couples

Seeking a romantic getaway in Montgomery? Explore the charming local vineyards for wine tasting, or take a scenic hike in the picturesque hills. For a delightful evening, enjoy a candlelit dinner at a quaint restaurant, savouring the flavours of the region together.

Things to do recommended for families

Families visiting Montgomery can explore the local heritage and enjoy a delightful day at the family-friendly playgrounds, paired with a scenic walk through the historic parks.

Things to do recommended for groups

Groups visiting Montgomery can enjoy a scenic hike at the nearby Mount Tom State Reservation, explore the charming local shops, and indulge in a delightful picnic at the picturesque Montgomery Park. Additionally, consider a guided tour of the historical sites that showcase the town's rich heritage.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Montgomery

Whether you're journeying with a group, travelling as a family, with your pets or seeking longer stays, be sure to select the appropriate filters. Here are some Stayz booking tips for you.

  • Traveling to Montgomery with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily apply filters for all these preferences and more on Stayz.
  • Traveling to Montgomery with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can greatly enhance your experience.
  • Taking your pets with you to Montgomery: For many, a family holiday is not complete without the presence of their beloved four-legged companion. If this resonates with you, explore Stayz properties that welcome pets. Typically, pet-friendly accommodations offer feeding dishes and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Montgomery: If you're seeking holiday lets with special rates for extended stays of a month or more, you've come to the right place. With the appropriate filter, you can effortlessly locate and secure savings on monthly rentals. You may also wish to include a parking space, a well-appointed kitchen, or a private pool in your search.

Where to stay near Montgomery

Discover the charm of Montgomery, Massachusetts, where the village atmosphere blends seamlessly with urban vibrancy. Explore the quaint Montgomery village, stroll through Montgomery Park, and experience the romantic allure of downtown Montgomery. Ideal for culture, entertainment and family-friendly escapes, this town offers a unique blend of business and leisure, making it a perfect destination for those seeking an enriching holiday experience.

  • Springfield: Located 23km from Montgomery, Springfield offers a dynamic city experience with a blend of city-themed, romantic, and family attractions. Visitors can enjoy a variety of activities, from amusement parks and music concerts to relaxing at a local resort. The area is also home to significant landmarks, including an event conference venue, a theme park, and a sports facility stadium, making it a versatile destination for diverse interests.
  • Northampton: Just 19km from Montgomery, Northampton is a vibrant city celebrated for its cultural and outdoor experiences alongside its urban attractions. The city invites travellers to engage in educational pursuits, attend music concerts, or enjoy a day on the ski field. Notable local landmarks include historic and modern college universities as well as a scenic lake, offering a rich blend of academic heritage and natural beauty.
  • West Springfield: Also 19km away from Montgomery, West Springfield caters to families and those seeking outdoor and entertainment-themed activities. The city is home to an arena entertainment facility, educational venues, and an amusement park. Its local highlights include a theme park, an event conference venue, and a modern college university, ensuring a well-rounded and engaging travel experience for all visitors.

Booking with Stayz is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay frequently results in significant savings. To discover the ideal Stayz property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz’s innovative Trip Board offers you a dedicated space to craft fresh journeys, pick up where you last left off, or review and organise your travel plans. Properties you have previously saved or booked can now be easily located under Potential, Upcoming, or Current Trips. To access your Trip Boards, simply visit: https://www.stayz.com.au/trips

**Based on Vrbo properties bookings.

Book a holiday rental for your Montgomery getaway

Learn about the unique charm of Montgomery with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Montgomery

Are you hoping to find attractions to visit in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Montgomery a fun spot to go on holiday. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Blandford Ski Area (5 mi / 8 km)
  • The Ranch Golf Club (8.8 mi / 14.1 km)
  • Maple Corner Farm Cross Country Ski Area (9.1 mi / 14.6 km)
  • Olympia Ice Center (11.3 mi / 18.2 km)
  • Lost Acres Vineyard (14.1 mi / 22.6 km)
  • Otis Ridge (14.4 mi / 23.2 km)

Exploring the natural landscape of Montgomery

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Montgomery is a great place to get outside. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Stanley Park (6.1 mi / 9.8 km)
  • Mount Tom (9 mi / 14.4 km)
  • Joe Mayer Field (9.1 mi / 14.6 km)
  • Look Memorial Park (11.6 mi / 18.7 km)
  • Brightwood Ave. Park (12 mi / 19.2 km)
  • Smith College Botanic Garden (12 mi / 19.3 km)

Travelling to and around Montgomery

Fly into Westfield, MA (BAF-Barnes Municipal), the closest airport, located 5.9 mi (9.5 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Springfield Union Station (ZSF), which is 13.6 mi (21.9 km) away.

Frequently asked questions

What are the top attractions in Montgomery?
In Montgomery, Massachusetts, visitors can enjoy a tranquil, rural atmosphere with a variety of outdoor attractions. The nearby Mount Tom State Reservation offers opportunities for hiking, picnicking, and enjoying scenic views of the Connecticut River Valley. This area is great for nature enthusiasts looking to explore the local flora and fauna.For those interested in history, the town's proximity to the larger city of Springfield allows for easy access to attractions such as the Dr. Seuss National Memorial Sculpture Garden and the Naismith Memorial Basketball Hall of Fame. Additionally, the charming local farms and orchards in Montgomery provide a unique, agrarian experience, especially during the harvest season when visitors can pick their own fruits and enjoy farm-fresh 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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