Wellesley vacation rentals

We found 3,010 vacation rentals — enter your dates for availability

Discover a selection of 12 homes and other vacation rentals in Wellesley that are perfect for your trip. Vacation homes offer the best amenities for you and your friends, family, or even pets, such as a garden and pool. At the end of the day, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Wellesley

Showing deals for:Jul 3 - Jul 10

Image gallery for Modern home-like 3BR2BA Retreat/Minutes to T

Interior
9.8 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)

Modern home-like 3BR2BA Retreat/Minutes to T

Boston

9% off
Price is $1,060
$7,417 for 7 nights
All fees included
Modern home-like 3BR2BA Retreat/Minutes to T

Find spaces that suit your style

Find out more about Wellesley

Why visit Wellesley

  • Cultural richness: Explore historic colleges and universities alongside art museums showcasing Wellesley’s heritage.
  • Family-friendly activities: Enjoy local parks and community events perfect for visitors of all ages.
  • Charming neighborhoods: Stroll through quaint streets lined with family homes and friendly locals.
  • Outdoor adventures: Take advantage of scenic outdoor spaces for hiking, picnicking, and relaxation.
  • Diverse accommodations: Choose from cozy apartments to spacious vacation homes tailored to your needs.

Popular types of accommodation in Wellesley

Discover your perfect getaway with our selection of vacation rentals in Wellesley, MA. From cozy apartments and spacious houses to modern condos, we have options to suit every traveler's needs. Whether you're looking for comfortable apartments in Wellesley or charming home rentals, our transparent listings make it easy to find the ideal place to stay. Enjoy savings and reassurance while exploring this beautiful town.

  • Apartments: The top choice for vacationers in Wellesley, offering convenience and comfort in a variety of styles.
  • Houses: A popular option for families and groups, providing spacious living and a home-like atmosphere.
  • Condos: Ideal for those seeking modern amenities and community features, perfect for a relaxing stay.
  • House Boats: A unique accommodation that lets you enjoy the charm of living on the water.
  • Villas: Luxurious spaces that offer privacy and upscale living for an unforgettable experience.**

Top attractions near Wellesley

Wellesley, Massachusetts, offers a delightful mix of cultural and family-friendly experiences. Visitors can explore historic and modern colleges and universities, as well as art museums that showcase the area’s rich heritage. Whether you're seeking outdoor adventures or educational opportunities, Wellesley has something for everyone, making it an ideal destination for culture-themed vacations.

  • Fenway Park: Experience the rich history of this iconic sports stadium, home to the Boston Red Sox. With its unique Green Monster wall and passionate fans, Fenway offers an exhilarating atmosphere that blends sports and culture, just 11 miles from Wellesley.
  • Harvard University: Explore the prestigious grounds of this historic university, known for its world-class education and stunning architecture. Immerse yourself in its cultural vibe while wandering through beautiful campus landmarks, located 10 miles from Wellesley.
  • Boston College: Visit this modern university that boasts a vibrant campus life and stunning views of the city. With its engaging city vibes and beautiful buildings, Boston College is just 7 miles from Wellesley.

Things to do recommended for couples

Planning a romantic getaway in Wellesley? Enjoy a lively night at Paradise Rock Club, unwind at Nails & Co spa for some pampering, or hit the slopes at Blue Hills Ski Area for a fun day outdoors. Each spot offers a unique experience for couples.

Things to do recommended for families

Families can unwind at Elm Bank Reservation, just 2 miles away, offering serene nature vibes. For excitement, visit Fun and Games Family Entertainment Center, located 5 miles away, packed with adventure. Don't miss Alumni Stadium, 7 miles away, perfect for sports enthusiasts seeking thrilling games.

Things to do recommended for groups

Explore the vibrant Harvard Square for shopping and entertainment, catch a film at the charming Coolidge Corner Theatre, or savor local brews at Samuel Adams Brewery. Each venue offers a unique experience, perfect for creating lasting memories with your group in Wellesley.

*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 Wellesley

If you're traveling with a group, your family, or pets, or if you're planning an extended stay, be sure to filter your options based on your key priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Wellesley with a group: Think about how many bedrooms you'll require, as well as additional features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Wellesley with young kids: Traveling with little ones can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Wellesley: For many, a family vacation isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wellesley: If you're in search of vacation rentals that offer discounts 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 Wellesley

Wellesley, Massachusetts, offers a delightful mix of culture and family-friendly vibes, making it an ideal vacation spot. Nearby neighborhoods charm visitors with their urban atmosphere and friendly people. Explore quaint streets lined with family homes, enjoy local parks, and experience the vibrant community. Whether you're seeking a romantic getaway or a fun-filled family adventure, Wellesley and its surrounding areas promise an unforgettable experience.

  • Boston: Boston is a vibrant metropolis steeped in history and culture, making it an essential stop for any traveler. Located a short drive from Wellesley, the city offers a rich tapestry of experiences, from educational institutions like Harvard and MIT to the bustling shopping centers of downtown. Visitors can enjoy live music concerts, explore centuries-old landmarks, and catch a game at the historic Fenway Park. With its charming neighborhoods, diverse dining options, and an abundance of cultural events, Boston provides a dynamic urban adventure perfect for families and culture enthusiasts alike.
  • Natick: Just 3 miles from Wellesley, Natick is a delightful city that blends suburban charm with urban convenience. Known for its family-friendly atmosphere, Natick features numerous shopping destinations, including the popular Natick Mall, offering a wide variety of retail options and dining experiences. The city is also home to the historic Natick High School and a vibrant local community that hosts events throughout the year. With easy access to recreational facilities and parks, Natick is ideal for families looking for fun activities, making it a convenient addition to your itinerary.
  • Needham: Also located 3 miles from Wellesley, Needham is a charming city that offers a blend of culture and community spirit. Ideal for families and cultural enthusiasts, Needham showcases modern educational institutions and historical landmarks, including its historic college campus. The city hosts various events, including music concerts and community gatherings, providing a vibrant atmosphere for visitors. With its well-maintained parks and recreational facilities, Needham is a great place to relax and enjoy the local community while being close to the excitement of Wellesley and Boston.

Best time to go to Wellesley

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.2°F (-2.1°C)Light RainMostly SunnyAverageSlightly Low
February29.7°F (-1.3°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 HighAverage
May58.6°F (14.8°C)Light RainMostly SunnySlightly HighSlightly High
June66.7°F (19.3°C)Light RainMostly SunnyAverageAverage
July73.8°F (23.2°C)Light RainMostly SunnyAverageAverage
August72.3°F (22.4°C)Light RainMostly SunnyAverageSlightly High
September65.1°F (18.4°C)Light RainMostly SunnyAverageAverage
October54.3°F (12.4°C)Light RainMostly SunnySlightly LowSlightly High
November42.8°F (6.0°C)Light RainMostly SunnySlightly LowAverage
December34.5°F (1.4°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you eager to save on your upcoming vacation? Flexibility with your travel dates can lead to significant savings, as prices can vary. Additionally, opting for a longer stay often results in even greater discounts. To discover the perfect Vrbo property that fits your budget, utilize our filters to narrow down your options by price, location, and type of vacation rental. We're here to help you find the best deal.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new vacations, pick up right where you left off, or easily view and organize your travel arrangements. You can find the properties you've saved and booked in the Potential, Upcoming, or Current Trips sections. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Wellesley getaway

The gardens and other outdoor surroundings create an inviting atmosphere in Wellesley. Renowned for its university setting, basketball games and ice skating, this city welcomes all visitors. Fenway Park and Harvard Square are just a couple of the must-sees in the area. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Wellesley

Are you searching for top things to see and do while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Wellesley a fun spot to vacation. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • New England Aquarium (13.1 mi / 21.1 km)
  • Encore Boston Harbor (13.3 mi / 21.3 km)
  • Fun and Games Family Entertainment Center (5.3 mi / 8.6 km)
  • The Skating Club of Boston (9.1 mi / 14.6 km)
  • Samuel Adams Brewery (9.8 mi / 15.7 km)
  • The Fens (10.2 mi / 16.4 km)

Exploring the natural features in Wellesley

Whether you're an active traveler or just want to spend some time taking in the scenery, Wellesley is a great place to get outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Boston Common (12.2 mi / 19.7 km)
  • Copley Square (11.6 mi / 18.7 km)
  • Boston Harbor (13.2 mi / 21.2 km)
  • Cochituate State Park (4.4 mi / 7.1 km)
  • Arnold Arboretum (8.6 mi / 13.9 km)
  • Walden Pond (10.1 mi / 16.3 km)

Transportation options to and around Wellesley

Fly into Norwood, MA (OWD-Norwood Memorial), the closest airport, located 9.6 mi (15.4 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Bedford, MA (BED-Laurence G. Hanscom Field), which is 11.5 mi (18.6 km) away.

If you're traveling by train, Wellesley Square Station, Wellesley Hills Station and Wellesley Farms Station are the main stations in the area.

Frequently asked questions

What is the best area to stay in Wellesley, Massachusetts, United States of America when booking a vacation rental?
When considering a vacation rental in Wellesley, Massachusetts, the best area to stay in is near the Wellesley Village neighborhood. This charming area is known for its picturesque streets and vibrant setting, making it a delightful base for your visit. Here, you'll find a range of properties that cater to various needs, from cozy apartments to spacious homes, offering a comfortable stay.

In Wellesley Village, you can explore the delightful shops and cafes that line the streets, creating a great blend of local culture and community spirit. One of the top attractions in the area is the Wellesley College campus, renowned for its stunning architecture and beautiful gardens, which are great for a leisurely stroll. Additionally, don't miss the opportunity to visit the nearby Wellesley Town Center, where you can experience a variety of dining options and boutique shopping.

Another noteworthy area is the Bates Neighborhood, which is characterized by its tranquil residential streets and proximity to scenic parks. This area offers a peaceful retreat while still being a short drive from the town's main attractions. The nearby Elm Bank Reservation is a highlight, featuring beautiful landscapes and trails that are ideal for outdoor enthusiasts.
How much does it cost to rent a vacation home in Wellesley?
Prices for vacation rentals in Wellesley 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Wellesley to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Wellesley vacation house rentals?
You can find great discounts on house rentals in Wellesley on Vrbo, 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.
What is the most popular type of vacation rental accomodation in Wellesley?
In Wellesley, vacation houses, apartments, and condos are all popular rental choices, with several options available in the area. These properties can be found in charming neighborhoods that offer a suburban feel, making them ideal for families and travelers seeking a quieter stay. Expect amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces like patios or gardens that provide a comfortable environment for relaxation.
Are there any family house rentals in Wellesley?
In Wellesley, Massachusetts, there are several family-friendly house rentals available, making it an excellent choice for those traveling with children. This charming town offers spacious properties that often come with amenities such as fully equipped kitchens, cozy living rooms, and outdoor spaces where families can enjoy barbecues or relax in the fresh air.

Visitors can explore nearby attractions, including the scenic Wellesley College campus, which features beautiful gardens and walking paths. Additionally, the town is close to parks like the Wellesley Town Forest, providing ample opportunities for hiking and outdoor activities.
Can I find long-stay vacation rentals in Wellesley?
A long-stay vacation rental in Wellesley is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Wellesley?
In Wellesley, travelers can find several pet-friendly house rentals that cater to a variety of needs. Many of these homes are equipped with modern amenities such as spacious kitchens, comfortable living areas, and outdoor spaces, which are great for families or groups traveling with pets. The neighborhood offers convenient access to local parks, providing ample opportunities for pet owners to enjoy walks and outdoor activities.

The nearby Wellesley College campus is home to beautiful grounds and walking paths, making it a lovely area for strolls with furry companions. Additionally, the Wellesley Town Center features pet-friendly cafes and shops, ideal for visitors traveling with pets. See all pet-friendly rentals in Wellesley.
Are there any remote work vacation rentals in Wellesley?
In Wellesley, Massachusetts, there are several remote work vacation rentals available that cater to the needs of travelers looking to combine work and leisure. Many of these properties feature essential amenities such as high-speed internet, Wi-Fi in rooms, and dedicated workspaces equipped with desks and chairs, making it easy to stay productive while enjoying the comforts of home.

The town itself offers a tranquil suburban atmosphere, superb for those seeking a peaceful environment for remote work. Additionally, Wellesley is known for its beautiful parks and outdoor spaces, which can provide a refreshing break from work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Wellesley vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Wellesley with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
What are popular rental amenities in Wellesley?
In Wellesley, popular vacation rental amenities cater to a range of traveler needs, with many properties featuring essential comforts like a kitchen for home-cooked meals, a deck or patio for outdoor relaxation, and onsite parking for convenience. Additionally, many rentals come equipped with a coffee and tea maker, ensuring guests can enjoy their morning beverages with ease. For those needing to work or study while away, several accommodations include a desk area, making it easy to stay productive.
When is the best time to visit Wellesley for a vacation rental?
The most popular time to visit Wellesley is during the vibrant spring months of March to May, with April standing out as a particularly delightful choice. This is when the area comes alive with blooming flowers and lush greenery, making it an ideal backdrop for outdoor activities and leisurely strolls. Travelers can enjoy the charming local parks, explore the scenic landscapes, and participate in community events that reflect the lively spirit of the season.

April typically boasts mild temperatures, ranging from the low 40s to mid-60s Fahrenheit, creating a comfortable environment for sightseeing and exploration. Whether you're wandering through the picturesque neighborhoods or visiting local shops and cafes, the pleasant weather enhances the overall experience.

For those who are budget-conscious yet still want to enjoy Wellesley's attractions, consider planning your visit in November. This month offers a quieter atmosphere, superb for appreciating the fall foliage and taking in the tranquil beauty of the area without the crowds.

Ultimately, choosing when to visit Wellesley depends on your preferences for vibrant springtime activities or the peaceful ambiance of early winter.
How early should I book a Wellesley vacation rental?
Book your Wellesley vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Wellesley, Massachusetts, United States of America?
In Wellesley, visitors can enjoy a variety of attractions that highlight the area's natural beauty and cultural offerings. The Wellesley College campus is a great site, featuring stunning architecture and the picturesque Wellesley College Botanic Gardens, which provide a peaceful retreat with walking paths and diverse plant life.

Nearby, the Hunnewell Estate and Gardens offers scenic views and a chance to experience the local environment, making it a lovely spot for leisurely strolls. The town center features charming shops and eateries, where visitors can explore local flavors and unique boutiques.

For outdoor enthusiasts, the Charles River provides opportunities for kayaking and canoeing, and the surrounding parks, like the Wellesley Town Forest, offer trails for hiking and nature walks.
Can I change or cancel my Wellesley home rental booking on Vrbo?
To find Wellesley vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Wellesley vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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