Holiday Rentals in Wellesley, MA

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Wellesley, MA holiday rentals
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55 Holiday rentals and Airbnb in Wellesley, MA

Best family friendly Wellesley, MA holiday rentals

Among the 55 accommodations in Wellesley, MA, here are the 4 best family friendly rentals

4br Family Vacation Home  Near Boston  Gillette Stadium    Free Parking - Wellesley, MA
10 2 reviews

4br Family Vacation Home Near Boston Gillette Stadium Free Parking

apartment, Norwood
This detached house in Norwood, MA, is situated approximately 25-35 minutes by car from Boston and 15-20 minutes from Gillette Stadium.
This fully furnished four-bedroom property accommodates up to eight guests, offering a private garden, off-street parking, high-speed WiFi, and a fully equipped kitchen, ideal for both short-term and extended stays.
Sunny, Spacious 2 Bed, Bus To Harvard, Open 30+days - Wellesley, MA
No reviews

Sunny, Spacious 2 Bed, Bus To Harvard, Open 30+days

apartment, Watertown Town
This 2-bedroom flat in Watertown offers direct bus access to Harvard University and Red Line connections to MIT, placing you within a short walk of amenities including a gas station, local markets, restaurants, CVS, 7-11, and Star Market.
This 91.5 square metre property accommodates up to 6 guests with two queen beds and a twin sofa bed, featuring a fully equipped kitchen with a Breville coffee machine, a dedicated workspace, and a shared outdoor lounge with a propane grill and cornhole game, ideal for extended stays of 30+ days.
Newton Family Home! Furnished! Family Friendly! - Wellesley, MA
10 1 review

Newton Family Home! Furnished! Family Friendly!

apartment, Newton
This furnished four-bedroom, two-bathroom Cape house in Newton offers a prime location with a convenient 32-kilometre commute to Boston, featuring a manicured, fenced garden with a swing set and a deck. This family-friendly property accommodates up to six guests and includes a modern kitchen with Subzero appliances, air conditioning, and laundry facilities, making it suitable for short-term 30-day rentals.
The Inn At Newton Highlands, Suite 2, Apartment-hotel - Wellesley, MA
10 167 reviews

The Inn At Newton Highlands, Suite 2, Apartment-hotel

apartment, Newton
This apartment in Newton Highlands is ideally located within easy reach of both Newton-Wellesley Hospital and Boston College, making it a convenient choice for visitors to these institutions. The apartment has received excellent ratings for location, cleanliness, and overall user experience, ensuring a comfortable and enjoyable stay.
This spacious three-bedroom flat can comfortably accommodate up to six guests, offering ample space for families or groups of friends. The apartment features a fully equipped kitchen, a terrace or balcony, a garden, and parking, as well as free Wi-Fi access and a dedicated arcade/game room, providing plenty of entertainment options for guests.

Best Wellesley, MA holiday rentals with parking

Quiet Hillside Apartment - Wellesley, MA
9.1 9 reviews

Quiet Hillside Apartment

apartment, Waltham
This one-bedroom flat in Waltham is situated a short walk from Moody Street, offering access to its restaurants, cafes, and shops, and is conveniently located just a few kilometres from the 90/95 interchange.
This pet-friendly apartment accommodates up to four guests, featuring a full kitchen, a dedicated workspace with dual monitors, and access to a shared outdoor BBQ grill, with on-site coin-operated laundry facilities also available.
Boston Single Family House - 19' Train To Back Bay - Wellesley, MA
9.7 8 reviews

Boston Single Family House - 19' Train To Back Bay

house, Boston
This Boston family home, situated in a quiet area approximately 11 kilometres from Boston University, the Hynes Convention Centre, the Museum of Fine Arts, and Fenway Park, offers convenient access to major attractions.
The 242 square metre property boasts a spacious five-bedroom layout sleeping up to 23 guests, complete with four bathrooms, a fully equipped kitchen, free Wi-Fi, private parking, and a terrace with garden views.
Renovated 1bed, Steps To Mbta, Shops & Restaurants - Wellesley, MA
9.0 1 review

Renovated 1bed, Steps To Mbta, Shops & Restaurants

apartment, Brookline
This renovated one-bedroom apartment in Brookline is conveniently located near the MBTA Green Line, offering easy access to Boston and is 3.5km from Fenway Park.
The 74-square-metre flat sleeps five, features a fully equipped kitchen with dishwasher, free Wi-Fi, and a spa, making it ideal for a comfortable Brookline stay.
Plannetsmart - Wellesley, MA
No reviews

Plannetsmart

apartment, Boston
This Planet Smart apartment is situated outside central Boston, approximately 10-13 kilometres from attractions such as the Museum of Fine Arts, Fenway Park, and Back Bay, offering convenient access by car or public transport.
This two-bedroom, one-bathroom flat boasts 111 square metres of space, sleeping up to 11 guests and including free private parking, a fully equipped kitchen, free Wi-Fi, and a shared lounge area.

Frequently asked questions about holiday rentals in Wellesley, MA

  • What are the top family-friendly attractions in Wellesley, MA?

    The Wellesley Free Library is a great place for families, with a dedicated children's area and regular events. The town also has a number of parks, including the beautiful Hunnewell Estate, perfect for a picnic or a game of frisbee.
  • What are the best Airbnb and holiday rentals in Wellesley, MA?

  • When is the best time to book a vacation rental in Wellesley, MA?

    It depends on what you're looking for. If you want to experience the town's vibrant autumn colours, book your rental in September or October. For warmer weather and outdoor activities, June and July are popular months.
  • What are the most popular Airbnbs in Wellesley, MA?

  • What events or festivals should visitors check out in and around Wellesley, MA?

    The Wellesley Farmers Market is a popular event held every Saturday from June to October, offering fresh produce and local crafts. In the spring, the town hosts the Wellesley Apple Blossom Festival, a celebration of the town's history and culture.
  • What are the best rentals for families and kids in Wellesley, MA?

  • What are the best restaurants with local dishes in Wellesley, MA?

    Wellesley has a great selection of restaurants. For a taste of local fare, try the Wellesley Farms Country Store, known for its classic New England dishes and friendly atmosphere. For something a bit more upscale, try The Cottage, which features fresh, seasonal ingredients and a charming setting.
  • What are the best rentals or Airbnbs with a jacuzzi in Wellesley, MA?

    Near Colleges + Train 2bd 2ba Quiet Entire Home and Us Open Hse are the best vacation rentals or Airbnb with a jacuzzi in Wellesley, MA.

  • What are the best walking or cycling routes in Wellesley, MA?

    The town has a network of walking and cycling paths, including the scenic Wellesley-Newton Rail Trail, which runs along the Charles River. For a more challenging ride, try the route that circles Lake Waban, offering beautiful views of the water and surrounding forests.
  • Are there pet-friendly attractions in Wellesley, MA?

    Many of Wellesley's parks are pet-friendly, including Hunnewell Estate and the Wellesley Town Hall Green. You can also find a number of pet-friendly restaurants and cafes in town.
  • What are the benefits of choosing a vacation rental in Wellesley, MA?

    Vacation rentals offer more space and privacy compared to hotels. They are often located in residential areas, providing a more authentic experience of the town. You can also find rentals with unique features and amenities that cater to your specific needs.
  • What are the top sports attractions and facilities in Wellesley, MA?

    Wellesley is home to the Wellesley High School, which has a variety of sports facilities, including a football field, tennis courts, and a swimming pool. There are also several private sports clubs and facilities in the town.

Popular destinations

Best Wellesley, MA holiday rentals with a balcony

West Roxbury Retreatnear Downtown Boston, Steps To Train & Bus,member Only Deal - Wellesley, MA
9.8 108 reviews

West Roxbury Retreatnear Downtown Boston, Steps To Train & Bus,member Only Deal

apartment, Boston
This comfortable house is located in West Roxbury, a Boston neighbourhood, within 10 kilometres of Boston College, Northeastern University, and Fenway Park. It has received excellent user ratings, making it a popular choice for travellers visiting the city.
The property offers three bedrooms and two bathrooms, accommodating up to six guests, with a floor area of 134 square metres. It features a range of amenities, including a fully equipped kitchen, a Jacuzzi, a garden, and a terrace, perfect for relaxing after exploring the city.
Unique & Peaceful Boston Home, Ideal For 2026 World Cup Visitor, Free Parking - Wellesley, MA
9.2 91 reviews

Unique & Peaceful Boston Home, Ideal For 2026 World Cup Visitor, Free Parking

apartment, Boston
This apartment is located in a tranquil neighbourhood in Boston, just 10km from the Boston Museum of Fine Arts and 11km from Fenway Park. It has consistently received excellent ratings for its cleanliness, location and overall experience.
The apartment is a spacious two-bedroom property with one bathroom, covering 88 square metres and comfortably accommodating up to five guests. It offers a range of amenities including a fully equipped kitchen, private garden, free parking, and a washing machine, making it ideal for families or groups of friends exploring Boston.
Roslindale Village Condos - Wellesley, MA
8.7 195 reviews

Roslindale Village Condos

apartment, Boston
This apartment is located in the Roslindale neighbourhood of Boston, approximately 8 kilometres from the Boston Museum of Fine Arts and Fenway Park, offering a peaceful retreat from the city centre. The property has received excellent ratings for cleanliness and user experience, with a very good location rating.
The apartment features a terrace or balcony, a seating area and a fully equipped kitchen with a microwave and coffee machine. Guests can enjoy complimentary Wi-Fi, bikes for exploring the city, air conditioning, satellite TV and access to nearby golfing and hiking opportunities.
Welcome In This Charming One Bedroom Apartment Located In Westwood. Worldcup2026 - Wellesley, MA
10 4 reviews

Welcome In This Charming One Bedroom Apartment Located In Westwood. Worldcup2026

apartment, Westwood
This one-bedroom flat is located in Westwood, 13 kilometres from Gillette Stadium and within easy reach of the Boston Museum of Fine Arts and Fenway Park.
This cosy apartment accommodates two guests and features a kitchen with a fridge, microwave, and dishwasher, plus air conditioning, a balcony, garden, and access to a fitness centre.

Best pet friendly Wellesley, MA holiday rentals

Among the 55 accommodations in Wellesley, MA, here are the 4 best pet friendly rentals

Quarter Finals Paradise With Theatre And Gym - Wellesley, MA
10 2 reviews

Quarter Finals Paradise With Theatre And Gym

apartment, Newton
This 836 square meter residence in Newton's Waban district offers excellent access to the D line for commutes to Boston and is a short drive from Boston College.
This property, ideal for up to nine guests, boasts three bedrooms, five bathrooms, a microwave oven, dishwasher, air conditioning, parking, and a private gym, alongside proximity to Waban Centre and Boston's cultural attractions.
Cozy 2-bedroom Apartment In Charming Dedham - Legacy Mall With Wifi - Wellesley, MA
9.2 13 reviews

Cozy 2-bedroom Apartment In Charming Dedham - Legacy Mall With Wifi

apartment, Dedham
This Dedham flat, conveniently located near Boston, offers easy access to attractions such as Fenway Park, Faneuil Hall Marketplace, Harvard Square, and Newbury Street, although precise distances aren't specified.
The two-bedroom, one-bathroom apartment sleeps four guests in two queen-sized beds, includes in-unit laundry, complimentary Wi-Fi, and is pet-friendly.
Modern Apt With Private Garage - Wellesley, MA
No reviews

Modern Apt With Private Garage

apartment, Waltham
This Waltham apartment, situated approximately 11-14 kilometres from Minute Man National Historical Park, Harvard Square, and Harvard University, offers convenient access to major attractions.
The 79-square-metre flat comprises one bedroom, one bathroom, and accommodates up to five guests, featuring a fully equipped kitchen, in-unit laundry, a private garage, free Wi-Fi, air conditioning, a swimming pool, and a fitness centre.
The Rock - Wellesley, MA
10 2 reviews

The Rock

apartment, Natick
This spacious apartment is situated on the Weston/Wayland line, a short 15-minute drive from Boston and its major colleges, offering a peaceful and scenic setting. The property is conveniently located for exploring the city's attractions, shops, and restaurants.
This four-bedroom home comfortably accommodates eight guests and features a well-equipped kitchen, four bathrooms, a garden, a swimming pool, and a fitness centre. Guests can enjoy a range of amenities, including a fireplace, a theatre room, a games room, a playground, a pizza oven, and three fire pits.
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