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Ashland vacation rentals

We found 106 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Ashland that are perfect for your trip. Vacation homes provide the amenities you need and want for your stay with friends, family, or just your pet, such as a pool and a washer and dryer. At the end of the day, you'll be able to choose a rental to meet everyone's needs, including a place that is accessible or non-smoking.
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  • All the privacy of home
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Find out more about Ashland

Find out more about Ashland

Why visit Ashland

  1. Outdoor Adventures: Enjoy a variety of recreational activities in the nearby state parks, perfect for hiking and picnics.
  2. Cultural Experiences: Attend the renowned Shakespeare Festival and other theatrical performances for a taste of local arts.
  3. Charming Downtown: Explore the vibrant downtown area, featuring delightful shops, restaurants, and stunning views.
  4. Family-Friendly Atmosphere: Engage in activities suitable for all ages, making it an ideal destination for families.
  5. Comfortable Accommodations: Choose from a range of vacation rentals, from cozy apartments to spacious homes.

Popular types of accommodation in Ashland

Planning a getaway to Ashland? You're in for a treat! Discover a range of popular vacation rentals in Ashland, including charming apartments, spacious houses, and modern condos. With our platform, you can easily compare Ashland hotels and find the perfect vacation rental that suits your needs. Enjoy transparency, savings, and peace of mind as you explore your options for an unforgettable stay in this beautiful destination.

  • Apartments: These are the top choice for vacation rentals in Ashland, offering comfortable and convenient living spaces for visitors.
  • Houses: A popular option for those seeking more privacy and home-like amenities, ideal for families or groups.
  • Condos: These well-equipped units provide a blend of comfort and luxury, making them a sought-after rental choice.
  • House Boats: For a unique experience, these floating accommodations offer a charming way to enjoy Ashland’s waterways.
  • Cottages: These quaint and cozy lodgings are perfect for a relaxing getaway in a picturesque setting.**

Top attractions in Ashland

Ashland, Massachusetts, is an ideal destination for outdoor enthusiasts and families alike, offering a blend of modern and historic attractions, including local colleges and state parks. Visitors can immerse themselves in the rich culture through various activities, such as exploring nearby destinations, attending the Shakespeare Festival, and enjoying theatrical extravaganzas. With its vibrant city atmosphere, Ashland promises memorable experiences for every traveller.

  1. Boston College: A vibrant modern university with a dynamic atmosphere, offering stunning architecture and a lively campus life just 25.7km away from Ashland.
  2. Hopkinton State Park: A beautiful national park located 6.4km from Ashland, perfect for outdoor enthusiasts with its scenic landscapes, trails for hiking, and various recreational activities.
  3. Wellesley College: A historic institution 12.9km from Ashland, renowned for its beautiful campus and rich cultural heritage, providing a glimpse into the academic excellence and women's empowerment.

Things to do recommended for couples

For a romantic getaway in Ashland, indulge in luxury at Westborough Country Club, relish the thrill of skiing at Ski Ward Ski Area, or enjoy live music at Showcase Live. Each spot offers a unique experience, perfect for couples seeking adventure and relaxation together.

Things to do recommended for families

In Ashland, families can catch a game at Gillette Stadium, enjoy thrilling activities at Apex Entertainment Center, or glide across the ice at New England Sports Center. Each location promises fun and excitement, making for a memorable family adventure!

Things to do recommended for groups

Explore the Natick Collection for shopping and entertainment, just 8.0km from Ashland. Swing by Pinecrest Golf Club for outdoor sports, located 6.4km away. Don’t miss American Girl Boston, a delightful store also 8.0km from Ashland, perfect for group activities.

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

When planning your trip—whether you're travelling with a group, family, pets, or seeking longer stays—it's important to prioritize your preferences. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Ashland with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Fortunately, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Ashland with young kids: Travelling with little ones can be quite demanding. It's important to prioritize their comfort and safety while also looking for age-appropriate amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Ashland: For many families, a trip wouldn’t feel complete without their furry companion. If this resonates with you, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home during your stay.
  • Planning for a long term stay visiting Ashland: If you're in search of vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Ashland

Ashland, Massachusetts, is a charming destination perfect for family-friendly adventures and outdoor escapades. Explore the vibrant downtown area, where you can find delightful accommodations and enjoy stunning views. Just a short walk from the heart of the city, visitors are greeted by a welcoming atmosphere filled with friendly locals. Whether you're seeking recreation or a romantic getaway, Ashland offers the ideal blend of experiences for every traveller.

  • Framingham: Located a mere 4.8km from Ashland, Framingham is a vibrant city that caters to families, business travellers, and those seeking a lively urban experience. Visitors can enjoy an array of activities, including shopping at the popular mall centres and catching a live music concert. The city's educational institutions add to its appeal, making it a great spot for learning and exploration. Notable attractions include a local stadium, a historic college university, and various sports facilities, ensuring there’s something for everyone.
  • Hopkinton: Just 6.4km away from Ashland, Hopkinton is a picturesque city renowned for its outdoor experiences and family-friendly atmosphere. Nature enthusiasts can explore scenic parks and trails, while music lovers can enjoy concerts throughout the year. The town is also home to the starting line of the famous Boston Marathon, adding a unique touch to its character. Key landmarks include the charming local streets, a well-known stadium, and a serene lake, all inviting you to soak in the natural beauty and community spirit.
  • Southborough: Also located 6.4km from Ashland, Southborough offers a perfect blend of family, outdoor, and sports experiences. It’s an ideal destination for those looking to engage in recreational activities, including ice skating and various sports events. The city is well-equipped with educational venues and regularly hosts live music events. Attractions in Southborough include a vibrant stadium, sports facilities, and a historic college university, making it a delightful place to visit for those seeking both fun and culture.

Best time to go to Ashland

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

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January28.0°F (-2.2°C)Light RainMostly SunnyAverageSlightly Low
February29.5°F (-1.4°C)Light RainMostly SunnyAverageSlightly Low
March36.7°F (2.6°C)Light RainMostly SunnySlightly HighSlightly Low
April47.8°F (8.8°C)Light RainMostly SunnySlightly HighSlightly High
May58.6°F (14.8°C)Light RainMostly SunnyAverageSlightly High
June66.7°F (19.3°C)Light RainMostly SunnyAverageAverage
July73.6°F (23.1°C)Light RainMostly SunnySlightly HighAverage
August72.1°F (22.3°C)Light RainMostly SunnyAverageAverage
September64.9°F (18.3°C)Light RainMostly SunnyAverageAverage
October54.1°F (12.3°C)Light RainMostly SunnySlightly LowSlightly High
November42.6°F (5.9°C)Light RainMostly SunnySlightly LowAverage
December34.3°F (1.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, refine your travel plans, or manage your existing bookings. The properties you’ve saved or reserved are thoughtfully categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Take in the lakeside beauty of Ashland

The lake and surrounding scenery provide a peaceful ambiance to your vacation home in Ashland. This city's shopping, hiking and restaurants draw many visitors. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Sightseeing in and around Ashland

Are you hoping to discover attractions to see in the area? Venture out of your cozy vacation rental and experience everything that makes Ashland a one-of-a-kind vacation spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Fun and Games Family Entertainment Center (4.3 mi / 6.9 km)
  • Massachusetts Horticultural Society's Gardens at Elm Bank (7.9 mi / 12.8 km)
  • Westborough Country Club (8.2 mi / 13.1 km)
  • Nashoba Valley Winery (14.1 mi / 22.7 km)
  • Fore Kicks Sports Complex and Golf Course (14.6 mi / 23.5 km)
  • Southwick's Zoo (15 mi / 24.1 km)

Exploring the natural features in Ashland

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Ashland is a great place to spend some time outside. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Cochituate State Park (5.5 mi / 8.9 km)
  • Garden in the Woods (5.7 mi / 9.2 km)
  • New England Wild Flower Society Garden in the Woods (5.9 mi / 9.5 km)
  • New England Baseball Complex (10.6 mi / 17 km)
  • Walden Pond (13.8 mi / 22.1 km)
  • DeCordova Sculpture Park and Museum (13.9 mi / 22.4 km)

How to get to and around Ashland

The nearest airport is in Norwood, MA (OWD-Norwood Memorial), located 15.5 mi (24.9 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Bedford, MA (BED-Laurence G. Hanscom Field), which is 16.7 mi (26.8 km) away.

If you prefer train travel, you can make your way to Ashland Station.

Frequently asked questions

How much does it cost to rent a vacation rental in Ashland?
The average price for a vacation home in Ashland is determined by several factors, such as length of stay, property type and season. Whether you’re searching for a sprawling villa with space for the whole family or a comfy cabin that’s perfect for two, just enter your dates of travel to discover stays with terrific value.
How much does it cost to rent a beach house in Ashland?
When you travel and the style and size of the property will determine the cost of your beachside vacation rental. Enter your Ashland travel dates to see your options on Vrbo. Did someone just say “private pool”? Use the filters to select the features and amenities you need.
What are the top attractions for families in Ashland?
Keeping the kids occupied during your stay in Ashland is a snap with these cool family-friendly attractions:

  • Apex Entertainment Center
  • Fun and Games Family Entertainment Center
  • Stoddard Park

How old do you have to be to rent a vacation rental in Ashland?
Age restrictions can vary across properties on Vrbo, so be sure to check the rules of the vacation rental in Ashland you’re interested in. But usually, it’s 16, 18 or 21.
How long can I rent a vacation rental in Ashland for?
How long you can rent a vacation rental in Ashland is down to the property. Just enter your preferred dates to display a list of options offering extended stays. With plenty of features like kitchens and air conditioning, as well as some offering weekly or monthly discounts, you’re sure to discover a terrific place to call your home away from home in Ashland.

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