Sherborn holiday rentals

We found 235 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Sherborn to find one that's perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for hanging out with the people that matter most, which might include a garden and hot tub. You're sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Sherborn

Showing deals for:13 Nov - 20 Nov

Interior
Exterior detail
Interior
Private kitchen
Exceptional
(6 reviews)

Luxury Tuscan style villa just few miles from downtown Boston .Newton Reg #24-17

Newton

9% off
AU$25,419
for 7 nights, 1 home
AU$3,631 per night
includes taxes & fees
Luxury Tuscan style villa just few miles from downtown Boston .Newton Reg #24-17
Exterior detail
Terrace/patio
Exterior
Private kitchen
Exceptional
(33 reviews)

Lovely Studio Walk to Wellesley and Babson College

Wellesley

8% off
AU$3,064
for 7 nights, 1 home
AU$438 per night
includes taxes & fees
Lovely Studio Walk to Wellesley and Babson College
Room
Interior
Living area
Private kitchen
Exceptional
(15 reviews)

Spacious 3-bedroom apartment in lovely Millis with AC, WiFi

Millis

8% off
AU$1,964
for 7 nights, 1 apartment
AU$281 per night
includes taxes & fees
Spacious 3-bedroom apartment in lovely Millis with AC, WiFi
Dining
Interior
Room
Private kitchen
Exceptional
(49 reviews)

The Inn at Newton Highlands, Suite 2, Apartment-Hotel

Newton

8% off
AU$5,150
for 7 nights, 1 apartment
AU$736 per night
includes taxes & fees
The Inn at Newton Highlands, Suite 2, Apartment-Hotel
Interior
Room
Private kitchen
Interior
Exceptional
(80 reviews)

The Inn at Newton Highlands, boutique apartment-hotel

Newton

12% off
AU$3,783
for 7 nights, 1 apartment
AU$540 per night
includes taxes & fees
The Inn at Newton Highlands, boutique apartment-hotel
Dining
Living area
Room
Exterior
Exceptional
(33 reviews)

Waterfront Lakehouse near FIFA Gillette Stadium, central to Boston & Providence

Wrentham

16% off
AU$6,078
for 7 nights, 1 home
AU$868 per night
includes taxes & fees
Waterfront Lakehouse near FIFA Gillette Stadium, central to Boston & Providence
Outdoor dining
Stairs to Apartment - We Shovel for You!
Living Room - Your Home Away from Home
Side Entrance - Winter
Exceptional
(24 reviews)

Large 5-Bed Modern Family Retreat with Kitchen & Free Parking Near Boston!

Boston

5% off
AU$1,570
for 7 nights, 1 apartment
AU$224 per night
includes taxes & fees
Large 5-Bed Modern Family Retreat with Kitchen & Free Parking Near Boston!

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Sherborn getaway

Learn about the unique charm of Sherborn with a stay in a holiday home rental. Renowned for its shopping, restaurants and sporting events, this city welcomes all visitors. Gillette Stadium and Fenway Park are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Sherborn

Are you hoping to find things to do during your stay? Venture out of your cosy holiday rental and check out everything that makes Sherborn a fun place to get away to. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Massachusetts Horticultural Society's Gardens at Elm Bank (4.1 mi / 6.5 km)
  • Fun and Games Family Entertainment Center (4.3 mi / 7 km)
  • The Skating Club of Boston (10.4 mi / 16.7 km)
  • Fore Kicks Sports Complex and Golf Course (11 mi / 17.6 km)
  • Brookmeadow Country Club (11.6 mi / 18.6 km)
  • Westborough Country Club (13.1 mi / 21 km)

Exploring the natural features in Sherborn

Whether you're an active traveller or just want to take in the scenery, Sherborn is a great place to get outside. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Boston Common (17.5 mi / 28.1 km)
  • Copley Square (16.9 mi / 27.1 km)
  • Cochituate State Park (4.9 mi / 7.8 km)
  • Chestnut Hill Reservoir (12.7 mi / 20.4 km)
  • Arnold Arboretum (13.2 mi / 21.3 km)
  • DeCordova Sculpture Park and Museum (13.4 mi / 21.6 km)

Transport options to and around Sherborn

The nearest airport is in Norwood, MA (OWD-Norwood Memorial), located 10.5 mi (16.8 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Bedford, MA (BED-Laurence G. Hanscom Field), which is 16.1 mi (25.9 km) away.

Frequently asked questions

What is the best area to stay in Sherborn when booking a holiday rental?
When considering a holiday rental in Sherborn, Massachusetts, the best area to stay would be near the charming town centre. This locality offers a delightful blend of tranquillity and convenience, making it ideal for a relaxing getaway. While Sherborn itself is primarily residential, its proximity to nearby attractions enhances the appeal of this area.One popular point of interest is the picturesque Farm Pond, which provides a lovely setting for outdoor activities such as walking, fishing, and picnicking. Additionally, the historic Sherborn Centre is home to quaint shops and local eateries, superb for sampling the community's culinary offerings.Sherborn features a modest number of properties available for holiday rental, suiting various tastes and budgets.
What is the most popular type of holiday rental accomodation in Sherborn?
In Sherborn, holiday houses are the predominant type of holiday rental, with several available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, providing a comfortable home-away-from-home experience. Many of these houses also come with outdoor spaces, such as gardens or patios, superb for enjoying the peaceful suburban setting.
Are there pet-friendly house rentals in Sherborn?
In Sherborn, Massachusetts, there are several pet-friendly house rentals available, making it a welcoming destination for travellers with furry companions. Many of these holiday homes come equipped with amenities such as spacious backyards, fully stocked kitchens, and comfortable living areas, ideal for families or groups.The town is known for its picturesque countryside, providing a tranquil setting for a getaway. Sherborn is close to various parks and recreational areas, where pets can enjoy the outdoors. Nearby options include the picturesque Farm Pond and the expansive Rocky Narrows Reservation, both of which offer scenic trails and open spaces great for walks and outdoor activities with pets.
Are there any remote work holiday rentals in Sherborn?
In Sherborn, Massachusetts, there are several holiday rentals that cater to remote work needs. Many of these properties offer essential amenities such as high-speed Wi-Fi and dedicated workspaces, ensuring a comfortable environment for those needing to balance work and leisure. The town itself boasts a picturesque setting with lush greenery and scenic walking trails, superb for unwinding after a productive day.Additionally, rentals in Sherborn typically provide family-friendly amenities, including spacious living areas and fully equipped kitchens, making them suitable for longer stays. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Sherborn?
In Sherborn, popular rental amenities include the allowance for pets, making it a great destination for travellers looking to bring their dogs and cats along. Many holiday rentals feature fitness facilities, which are great for guests wanting to maintain their workout routines during their stay. Additionally, onsite parking is commonly available, providing convenience for those driving to the area. Service animals are also permitted in many properties, ensuring that guests with specific needs can enjoy their stay comfortably.
When is the best time to visit Sherborn for a holiday rental?
June is the most popular month to visit Sherborn, marking the beginning of the peak season that extends through to August. This time of year is great for those who enjoy warm weather and outdoor activities, as visitors flock to the area to take advantage of the beautiful surroundings and vibrant community events.During the summer months, you can expect comfortable temperatures ranging from 15 to 30 degrees Celsius, ideal for exploring the charming town and its picturesque parks. The longer days provide ample time for leisurely strolls, picnics, and enjoying local festivals that showcase the area's culture and hospitality.For those looking for more budget-friendly options, April offers a delightful alternative. While it's considered the low season, this month brings the beauty of spring as flowers bloom and the landscape comes to life. It's a wonderful time for quiet exploration and enjoying the natural beauty of Sherborn, making it an excellent choice for travellers seeking a peaceful retreat.Ultimately, the best time to book a holiday rental in Sherborn depends on your preferences. If you thrive in a lively option filled with community events and outdoor fun, summer is your best bet. However, if you appreciate a quieter experience with the charm of spring, April could be the great time for your visit.
What are the top attractions in Sherborn?
In Sherborn, visitors can enjoy a peaceful escape with a variety of attractions amidst its scenic countryside. The town is known for its beautiful conservation areas, including the Sherborn Town Forest and the picturesque Farm Pond, which offer trails for walking, hiking, and nature observation.For those interested in local history, the Sherborn Historical Society provides insights into the town's rich heritage, while the nearby Boston Nature Centre offers educational programmes and lovely walking paths through diverse habitats.Additionally, Sherborn is home to several charming farms and gardens, such as the top Wellesley College Greenhouses, which can provide a serene atmosphere for a leisurely visit.
Are all fees included in the Sherborn 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 Sherborn holiday homes with parking?
Stayz offers a wide selection of holiday homes in Sherborn 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 Sherborn holiday homes?
You can find great discounts on holiday homes in Sherborn 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 Sherborn holiday home booking on Stayz?
To find Sherborn 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 Sherborn?
A long-stay holiday home in Sherborn 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 Sherborn holiday home?
Book your Sherborn 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 Sherborn?
Prices for holiday homes in Sherborn 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 Sherborn 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.