Best Vacation Homes in Sherborn
New
House
4 Bedrooms
2 Baths
10 Guests
Hot Tub
Fireplace/Heating
Balcony/Terrace
Pet Friendly
R15,150/Night
7 Nights - R106,047
House
10.0(5 Reviews)
1 Bedroom
1 Bath
2 Guests
538.2 ft²
- Balcony/Terrace
Kitchen
Parking
Air Conditioner
R2,060/Night
7 Nights - R14,420
Hotel
9.6(756 Reviews)
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Kitchen
R2,957/Night
7 Nights - R20,699
House
5 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
Internet
R10,044/Night
7 Nights - R70,303
Apartment
10.0(1 Review)
3 Bedrooms
1 Bath
6 Guests
1097.92 ft²
- Fireplace/Heating
View- Parking
- Air Conditioner
R7,258/Night
7 Nights - R50,807
Cottage
10.0(4 Reviews)
2 Bedrooms
2 Baths
3 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R5,549/Night
7 Nights - R38,843
Apartment
8.0(1 Review)
1 Bedroom
1 Bath
3 Guests
Child Friendly
Security/Safety
R2,003/Night
7 Nights - R14,024
House
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
- Child Friendly
Laundry
R5,742/Night
7 Nights - R40,194
Sherborn Luxury Rentals
House
1 Bedroom
4 Baths
8 Guests
3702.79 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
R125,603/Night
7 Nights - R879,229
House
1 Bedroom
4 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R122,611/Night
7 Nights - R858,266
House
10.0(14 Reviews)
5 Bedrooms
3 Baths
8 Guests
3800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R70,468/Night
7 Nights - R493,272
New
House
5 Bedrooms
4 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R26,334/Night
7 Nights - R184,343
House
6 Bedrooms
7 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R21,694/Night
7 Nights - R151,861
House
10.0(6 Reviews)
4 Bedrooms
2 Baths
8 Guests
1507 ft²
Private Pool- Fireplace/Heating
Pool- Balcony/Terrace
R19,899/Night
7 Nights - R139,303
House
10.0(5 Reviews)
5 Bedrooms
2 Baths
10 Guests
2400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R15,935/Night
7 Nights - R111,552
House
5 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R14,064/Night
7 Nights - R98,450
Sherborn Pet Friendly Vacation Rentals
House
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R3,588/Night
7 Nights - R25,115
House
8.3(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
3164.59 ft²
- Pet Friendly
- Parking
- Internet
- Child Friendly
R10,871/Night
7 Nights - R76,104
Hotel
7.4(1010 Reviews)
1 Bath
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
R2,006/Night
7 Nights - R14,041
Apartment
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R3,545/Night
7 Nights - R24,819
House
4 Bedrooms
2 Baths
8 Guests
1506.95 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Air Conditioner
R12,327/Night
7 Nights - R86,288
House
9.8(7 Reviews)
4 Bedrooms
2 Baths
8 Guests
3164 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R11,891/Night
7 Nights - R83,239
House
10.0(12 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
R13,327/Night
7 Nights - R93,292
House
10.0(11 Reviews)
3 Bedrooms
2 Baths
6 Guests
1250 ft²
- Fireplace/Heating
- Ocean View
- View
- Pet Friendly
R11,222/Night
7 Nights - R78,559
Sherborn Large Vacation Homes
House
9.6(43 Reviews)
3 Bedrooms
3 Baths
10 Guests
2 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R10,277/Night
7 Nights - R71,934
House
9.0(9 Reviews)
3 Bedrooms
2 Baths
10 Guests
2150 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R7,337/Night
7 Nights - R51,351
House
4 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R8,903/Night
7 Nights - R62,326
House
3.3(3 Reviews)
5 Bedrooms
2 Baths
11 Guests
- Kitchen
- Air Conditioner
- Laundry
TV
R4,927/Night
7 Nights - R34,492
House
2.0(1 Review)
7 Bedrooms
6 Baths
15 Guests
- Private Pool
- Hot Tub
Spa- Fireplace/Heating
R37,061/Night
7 Nights - R259,425
House
5 Bedrooms
2 Baths
6 Guests
- Air Conditioner
- Child Friendly
- Security/Safety
R9,707/Night
7 Nights - R67,946
New
House
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R10,104/Night
7 Nights - R70,731
Why Choose Rent By Owner for your Sherborn Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Sherborn
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this charming destination can enhance your experience, as each season offers unique opportunities to enjoy the area's natural beauty and local charm while ensuring a memorable stay in your preferred vacation rental.
Peak Season Highlights
late spring to early summer (May to June)
During this time, the weather becomes warmer and more inviting, making it ideal for outdoor activities and exploring the scenic surroundings of this destination.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
early fall (September to October)
This period offers pleasant temperatures and vibrant foliage, perfect for enjoying the natural beauty of the region while booking your vacation rentals.
Average Temperature Daytime: 60-70°F - Nighttime: 45-50°F
Off-Season Highlights
winter (December to February)
The winter months bring cooler weather, which can be a quieter time to enjoy the region's cozy accommodations without the crowds.
Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
late fall to early winter (November)
As the vibrant fall colors fade, this off-peak season offers a peaceful retreat with fewer visitors and more availability for your stay.
Average Temperature Daytime: 50-55°F - Nighttime: 35-40°F
Weekly Weather Forecast for Sherborn
How to Book Your Sherborn Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Sherborn
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy your outdoor gatherings with a spacious patio or deck area, perfect for relaxing and entertaining.
- Take advantage of private gardens or landscaped yards that offer a peaceful setting in this charming area.
- Make the most of outdoor dining spaces for meals al fresco during your stay here.
- Utilize the property’s outdoor fire pits or fireplaces for cozy evenings after exploring the region.
- Experience the convenience of on-site parking facilities designed to accommodate your outdoor needs.
- Benefit from access to scenic walking trails or nature paths directly from the rental property.
- Relax by the private swimming pool or hot tub, providing a refreshing way to unwind after your adventures in the region.
Top Attractions Around Sherborn
What attractions are nearby?
Within this charming area, you can enjoy a variety of outdoor activities, explore scenic parks, and discover local attractions that make your stay in Sherborn, Massachusetts, truly memorable.
Family Activities
- Farm Pond Park: Enjoy a family picnic, paddle boating, or leisurely walking around the scenic pond in this peaceful outdoor space in Sherborn.
- Mass Audubon's Moose Hill Wildlife Sanctuary: Discover local wildlife through easy hiking trails and educational programs suitable for children, making it a great outdoor activity here.
- Sherborn Town Forest: Explore the lush trails perfect for family hikes and nature walks while experiencing the natural beauty of the area.
- The Sherborn Community Center: Participate in family-friendly events, sports activities, and wellness programs that foster community engagement locally.
Adult Activities
- Exploring the Local Trails: Enjoy a peaceful hike or bike ride along scenic trails that showcase the natural beauty of this destination's surroundings.
- Golfing at Nearby Courses: Tee off at top-rated golf courses in the region, perfect for relaxing afternoons and improving your swing amidst tranquil landscapes.
- Visiting Cultural Sites: Experience the area's rich history and local heritage by exploring museums and historical landmarks nearby.
- Dining at Local Restaurants: Savor delicious regional cuisine at charming eateries that highlight the culinary flavors unique to this part of the region.
Other Places to Stay in Sherborn, MA
Rocky Narrows
Sherborn Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Nature Trails: Take advantage of the area's scenic outdoor spaces to enjoy peaceful walks and connect with nature during your stay.
- Visit Nearby Cultural Spots: Discover local museums, galleries, or historical landmarks that showcase the unique heritage of this destination.
- Plan Seasonal Activities: Check out seasonal events and activities in the region to experience local traditions and festivities firsthand.
- Choose Strategic Accommodation Locations: Select a vacation rental centrally located within the area to maximize your convenience and access to top attractions.
Transportation Options
- Boston Logan International Airport: You can access the region easily via this major airport, which offers numerous domestic and international flights close to Sherborn’s outdoor attractions.
- Amtrak Commuter Rail Service: This service connects nearby towns to Boston, providing a convenient rail option for exploring the city and returning to this peaceful area.
- Local Bus Services: Managed by regional transit authorities, these buses offer reliable transportation within the region, making day trips or local errands simple.
- Private Car Services and Rideshare Apps: For personalized travel around here, rideshare options allow you to comfortably reach nearby destinations without hassle.
Local Customs Options
- New England Hospitality: You’ll notice residents’ warm, welcoming attitude that reflects the region's rich tradition of friendly, neighborly interactions.
- Local Farming Customs: Engaging with farm-to-table dining experiences highlights the area's longstanding agricultural roots and appreciation for fresh, local produce.
- Seasonal Celebrations: Participating in seasonal festivals and events showcases the area's vibrant community spirit and respect for traditional festivities.
- Historical Preservation: Respect for historical sites and architecture in this destination underscores the area's dedication to maintaining its cultural heritage.
Frequently Asked Questions About Sherborn?
1. What are the top vacation rentals in Sherborn?
There are a lot of options in Sherborn. If you plan on staying in the Sherborn area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Sherborn:
- Beautiful home in Wellesley's Historic district
- Lake Cochituate Waterfront Home
- Jamaica Plain Condo
- Cozy Boston Homestead : Sleeps 8, Pet Friendly
- Luxury Boston Ranch –Sleeps 8|Pet+|Private pool
- Infant-friendly Luxurious 7 Beds, 6 Room Home with BONUS Loft! A Dream Getaway!
- Big Bedroom on Lower Level, 65 inch TV, Netflix, Desk, Dining Table, Framingham Center
- Enchanted Cottage on 5 Acresnn
- Luxury Furnished Home, Spa Bath + Steam Shower Wellesley
- Comfortable 3 Bed Apt in Quiet Neighborhood
2. Which vacation homes in Sherborn are best for families?
If you are looking for a family-friendly vacation home in Sherborn, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Sherborn:
3. How many Rentbyowner vacation rentals are available in Sherborn?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 86 in the Sherborn area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Sherborn.
4. What is the cancellation policy for vacation rentals in Sherborn, Massachusetts?
Cancellation policies vary by property. To understand the specific terms regarding cancellations and refunds for your chosen rental in this area, please review the listing details or contact the property owner directly.
5. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning fees, service charges, or security deposits are often specified in the listing. For complete fee details, consult the property description or reach out to the host before confirming your reservation.
6. How do I inquire about availability and book a vacation rental in this region?
Availability can be checked through the listing calendar on the booking platform. Once you find a suitable rental, you can proceed with the reservation by following the booking instructions or contacting the owner for further assistance.
7. What amenities are typically included in vacation rentals in Sherborn, Massachusetts?
Most properties offer essentials like Wi-Fi, parking, heating or air conditioning, and kitchen facilities. For a full list of amenities, always review the property listing or communicate directly with the owner to ensure your needs are met.
8. Is it possible to get assistance if I encounter issues during my stay in this destination?
Support is available through the booking platform’s customer service, and owners are usually responsive to guest inquiries. For urgent matters, refer to the contact information provided in your reservation confirmation or the property's listing.
Sherborn Top Rated Vacation Rentals
R2,172/Night
7 Nights - R15,211
Hotel
8.9(343 Reviews)
1 Bath
357.9 ft²
- Private Pool
Oceanfront- Fireplace/Heating
- Pool
R2,653/Night
7 Nights - R18,573
