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.

The information above was last updated:

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:

  • Six Flags New England (15.7 mi / 25.3 km)
  • Blandford Ski Area (5 mi / 8 km)
  • The Ranch Golf Club (8.8 mi / 14.1 km)
  • Olympia Ice Center (11.3 mi / 18.2 km)
  • Edgewood Golf Course (11.8 mi / 19 km)
  • Lost Acres Vineyard (14.1 mi / 22.6 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:

  • Courtney Courtyard (5.4 mi / 8.7 km)
  • Littleville Lake (5.9 mi / 9.5 km)
  • Stanley Park (6.1 mi / 9.8 km)
  • Westfield River (6.7 mi / 10.7 km)
  • Holcomb Park (6.8 mi / 10.9 km)
  • Chester Center Historic District (7.9 mi / 12.7 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

How much does it cost to rent a holiday home in Montgomery?
The average price for a holiday home in Montgomery is based on a number of factors, such as property type, length of stay and time of year. Whether you're in search of a sprawling villa with space for extended family or a cosy cottage ideal for just you and the kids, just add your travel dates to discover stays with exceptional value.
How much does it cost to rent a beach house in Montgomery?
The average price for a holiday home near the beach in Montgomery depends on when you're going and the size and style of property you're looking for. Find prices quickly and easily on Stayz by entering your travel dates. Then use the filter tool to choose the number of bedrooms and amenities important to you, like WiFi, air conditioning and a pool.
What are the top attractions for families in Montgomery?
Hampton Ponds State Park will keep your kids entertained during your Montgomery escape. This family-friendly attraction is located near the centre.
How old do you have to be to rent a holiday home in Montgomery?
The minimum age is normally 16, 18 or 21. It can change from property to property on Stayz, so check the rules of your chosen Montgomery holiday home before booking.
How long can I rent a holiday home in Montgomery for?
The amount of time you can rent a Montgomery holiday home for is up to the property. Simply tap in your preferred travel dates to see options offering extended stays. They have everything you need to make your extended trip more enjoyable and convenient, like laundries and air conditioning. Some Stayz holiday homes may also offer weekly or monthly discounted prices, so you can have a longer stay for less.