Holliston vacation rentals

We found 129 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Holliston to find one that's perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation homes have the amenities you need and want for your stay, including WiFi and parking. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.
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Find out more about Holliston

Find out more about Holliston

Why visit Holliston

  1. Outdoor Recreation: Holliston offers numerous parks and outdoor activities, perfect for families and nature lovers.
  2. Charming Neighbourhoods: Explore friendly communities like Ashland and Milford, known for their welcoming atmosphere.
  3. Historic and Modern Colleges: Discover a blend of educational institutions that add to the town's vibrant culture.
  4. Diverse Accommodation Options: Choose from spacious apartments, cozy homes, and modern condos for a comfortable stay.
  5. Community Spirit: Experience a lively local vibe with community events and recreational opportunities.

Popular types of accommodation in Holliston

Discover the charm of Holliston with our selection of vacation rentals. Whether you prefer spacious apartments, cozy private homes, or modern condos, we have the perfect option for every traveller. From Holliston house rentals to bedroom rentals, find the ideal accommodation that suits your needs. Enjoy your stay in this delightful community, knowing you have transparency, savings, and reassurance with every booking.

  • Apartments: The leading choice for vacation rentals in Holliston, offering convenient living spaces for individuals and families alike.
  • Houses: A popular option for those seeking a home-away-from-home experience, perfect for groups or families wanting privacy.
  • Condos: Ideal for travellers looking for modern amenities and a community atmosphere during their stay in Holliston.
  • House Boats: A unique lodging experience on the water, providing a different perspective of the beautiful surroundings.
  • Cottages: These quaint and charming retreats offer a cozy ambiance, perfect for a peaceful getaway.**

Top attractions in Holliston

Holliston, Massachusetts, is an ideal destination for outdoor enthusiasts and families alike, offering a blend of historic and modern colleges, as well as national and state parks. Visitors can enjoy a variety of cultural and recreational activities, making it perfect for those seeking an engaging family experience. Be sure to explore the outdoor recreation options in and around Holliston to fully appreciate the area's natural beauty and vibrant community.

  1. Fenway Park: A historic sports stadium that embodies the spirit of Boston. Experience the excitement of a Red Sox game in this iconic venue, rich with culture and sporting history, located 32.2km from Holliston.
  2. Harvard University: Renowned for its academic excellence, this historic institution offers stunning architecture and a vibrant campus atmosphere, allowing visitors to soak in the rich culture, also 32.2km away.
  3. Boston College: A modern university with a picturesque campus that merges city vibes and natural beauty, providing a unique setting for exploration, located 25.7km from Holliston.

Things to do recommended for couples

For a romantic getaway in Holliston, consider enjoying a concert at Showcase Live, just 16.1km away, or indulge in luxury at Westborough Country Club, 19.3km away. If you're into winter sports, the Blue Hills Ski Area, 24.1km away, offers a delightful ski experience for couples.

Things to do recommended for families

Your family vacation in Holliston, Massachusetts, promises delightful experiences. Visit Gillette Stadium for thrilling sports excitement, explore the adventurous Apex Entertainment Center, or unwind at the serene Rocky Narrows, perfect for relaxation and wellness. Enjoy every moment of your trip!

Things to do recommended for groups

In Holliston, groups can enjoy shopping and entertainment at Patriot Place, try their luck at Plainridge Park Casino, and unwind with a round of golf at Pinecrest Golf Club. Each venue offers unique vibes, making for a memorable local experience.

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

If you're travelling with a group, family, pets, or planning an extended stay, it's important to filter your options according to your specific needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Holliston with a group: Think about how many bedrooms you'll require, as well as any amenities like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these features and more on Vrbo.
  • Traveling to Holliston with young kids: Traveling with young children can be quite an adventure, but it does come with its challenges. It's important to prioritize their comfort and safety, along with amenities that are suitable for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Holliston: For many families, a vacation wouldn’t feel complete without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Holliston: If you’re in search of vacation rentals offering discounts for month-long stays, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to consider additional features such as a parking spot, a well-equipped kitchen, or even a private pool in your search.

Where to stay in Holliston

Holliston, Massachusetts, is a delightful destination for outdoor enthusiasts and families alike. With its charming neighborhoods and friendly atmosphere, visitors can explore nearby towns such as Ashland and Milford, known for their welcoming vibes and budget-friendly options. Enjoy sports activities, local parks, and excursions that highlight the area's natural beauty. Holliston's blend of community spirit and recreational opportunities makes it a perfect spot for a memorable vacation.

  • Medway: Medway is a charming city located 3.2km from Holliston, offering a delightful mix of outdoor activities and scenic beauty. Visitors can enjoy various sports, including golf at local courses, or attend lively music concerts. The city's attractions include a prominent sports facility stadium, perfect for catching an exciting game, as well as a nearby beach for a relaxing day by the water. Medway's picturesque landscapes and vibrant community spirit make it an ideal spot for a fun day trip.
  • Millis: Situated 4.8km from Holliston, Millis is a quaint city that combines romance with outdoor charm. It’s a great destination for couples looking to enjoy time together while exploring local parks and lakes. Millis hosts music concerts and offers educational opportunities, making it a well-rounded experience for visitors. Key attractions include its sports facility stadium and recreational lakes, where you can partake in various activities or simply unwind and enjoy the scenery.
  • Sherborn: Located 6.4km from Holliston, Sherborn is known for its serene environment and urban charm. This city is perfect for those who appreciate outdoor experiences and scenic views. Visitors can explore educational venues, enjoy music concerts, or indulge in shopping at local centres. The area features a sports facility stadium and beautiful lakes, providing ample opportunities for recreation and relaxation. Sherborn's welcoming community and rich attractions make it a lovely addition to any itinerary.

Best time to go to Holliston

If you're planning a trip to Holliston, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March, May and July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January28.4°F (-2.0°C)Light RainMostly SunnySlightly LowSlightly Low
February30.0°F (-1.1°C)Light RainMostly SunnyAverageSlightly Low
March36.9°F (2.7°C)Light RainMostly SunnySlightly HighSlightly Low
April47.8°F (8.8°C)Light RainMostly SunnyAverageSlightly High
May58.5°F (14.7°C)Light RainMostly SunnySlightly HighSlightly High
June66.4°F (19.1°C)Light RainMostly SunnyAverageAverage
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighAverage
August72.1°F (22.3°C)Light RainMostly SunnyAverageAverage
September64.9°F (18.3°C)Light RainMostly SunnyAverageAverage
October54.5°F (12.5°C)Light RainMostly SunnyAverageSlightly High
November43.2°F (6.2°C)Light RainMostly SunnySlightly LowAverage
December34.5°F (1.4°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as this can lead to significant savings. Additionally, opting for a longer stay often results in even better deals. To discover the ideal Vrbo property that fits your budget, make use of our helpful filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume your previous ones, or manage your travel arrangements. You can easily access your saved or booked properties, all neatly organized under Potential, Upcoming, or Current Trips. To begin exploring the benefits of Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Delight in the lakeside landscape of Holliston

The lake and beaches create a pretty picture of Holliston. Renowned for its hiking, boating and golfing, this city welcomes all visitors. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Holliston

Do you want to discover attractions to visit in the city? Venture out of your vacation home and experience everything that makes Holliston a fun place to get away. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Fun and Games Family Entertainment Center (8 mi / 12.8 km)
  • Massachusetts Horticultural Society's Gardens at Elm Bank (8.4 mi / 13.5 km)
  • Fore Kicks Sports Complex and Golf Course (8.9 mi / 14.3 km)
  • Family Funway Foxboro (10 mi / 16 km)
  • Supercharged Entertainment (11.3 mi / 18.1 km)
  • Plainridge Race Course (11.8 mi / 19 km)

Exploring the natural features in Holliston

Whether you're looking for adventure or just want to take in the scenery, Holliston is a great place to spend some time outside. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Framingham Town Common (8.2 mi / 13.2 km)
  • Cochituate State Park (8.8 mi / 14.2 km)
  • Wayland Town Beach (9.5 mi / 15.3 km)
  • Lake Chauncy Public Beach (12.3 mi / 19.9 km)
  • New England Baseball Complex (14.7 mi / 23.6 km)
  • Chestnut Hill Reservoir (16.8 mi / 27 km)

How to get to and around Holliston

Fly into Norwood, MA (OWD-Norwood Memorial), the closest airport, located 12.2 mi (19.6 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Pawtucket, RI (SFZ-North Central State), which is 18.7 mi (30.1 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Holliston?
Based on our data, houses are the most popular type of property in Holliston. But as you'd expect, everyone's idea of an awesome stay can vary. Vrbo has vacation rentals with every size, shape and budget in mind, so you're sure to discover your perfect match.
How much does it cost to rent a vacation rental in Holliston?
Several things can determine what you'll pay for your vacation rental in Holliston, like the season, length of stay and type of property. But, all our vacation homes have one thing in common — unbeatable value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Holliston?
When you travel and the size and style of the property will influence how much you'll pay for your beachside stay. Enter your Holliston travel dates to view your available options on Vrbo. Did someone just say "private pool"? Use our filters to select the amenities and features you want in your beach house.
What are popular rental amenities in Holliston?
When it comes to rental amenities that guests search for in Holliston, a garden, a barbecue grill and a nearby river are the most popular. With Vrbo vacation homes, you'll enjoy choices to match your taste and style, whether you're going on a vacation with friends, family or even pets.
What are the top attractions for families in Holliston?
Keep the kids entertained at these fantastic family-friendly attractions in Holliston:

  • Stoddard Park
  • Pleasure Point
  • Hopkinton State Park

How old do you have to be to rent a vacation rental in Holliston?
The minimum age is typically 16, 18 or 21. It can differ from property to property on Vrbo, so look at the rules of your chosen Holliston vacation home before you book.
How long can I rent a vacation rental in Holliston for?
It's up to the Holliston property. To see all available options offering extended stays, simply enter your travel dates and number of guests into Vrbo. You can look forward to having the place to yourself, along with home comforts like a kitchen, air conditioning and a backyard where the little ones can play. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.

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