Vacation rentals in Wellesley, MA

55 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Wellesley, MA vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Wellesley, MA

Find Vacation Rentals in Downtown of Wellesley, MA

Choose a downtown Wellesley, MA vacation rental for easy sightseeing. Compare the top centrally located properties and book your city stay with confidence.

Luxury Boston Mansion | Outdoor Gardens + Sauna - Wellesley, MA
10 2 reviews

Luxury Boston Mansion | Outdoor Gardens + Sauna

apartment, Wellesley
This Wellesley home is a fully restored Victorian house located just 20 minutes from downtown Boston and situated at the halfway point of the Boston Marathon route, making it ideal for runners and those looking to explore the city. The safe and private neighborhood provides a peaceful setting, perfect for relaxing after a day of sightseeing.
This spacious house has six bedrooms and four bathrooms, comfortably accommodating up to 14 guests. Enjoy modern amenities like air conditioning, a fully equipped kitchen, and a fitness center, along with charming features like a farmers porch and a spacious backyard with a fire pit.
Airy, Sunny, Clean 2 Br In Waltham- 15 Min Bos - Wellesley, MA
9.7 444 reviews

Airy, Sunny, Clean 2 Br In Waltham- 15 Min Bos

apartment, Newton
This Waltham apartment, bordering West Newton, offers easy access to Moody Street's restaurants, shops, and a movie theater, and is a 15-minute drive from Boston.
This two-bedroom, one-bathroom unit sleeps eight, features a fully equipped kitchen with granite countertops, free Wi-Fi, a 39" flat-screen TV, off-street parking, and a shared washer/dryer; nearby colleges include Brandeis, Regis, Bentley, and Lasell.
Swan Manor Overlooking The Charles River - Wellesley, MA
9.6 48 reviews

Swan Manor Overlooking The Charles River

apartment, Natick
This Natick apartment rental is conveniently located near the Charles River, a five-minute walk from the Charles River Coffee House, with easy access to walking trails and a community organic farm.
This one-bedroom, one-bathroom unit sleeps three guests and features a private entrance, a patio with a fire pit, kayak and canoe access, and a fully equipped kitchen including a refrigerator, freezer, and microwave.
The Inn At Fireside Tavern Sherborn - Wellesley, MA
8.8 3 reviews

The Inn At Fireside Tavern Sherborn

hotel, Sherborn
The Inn at Fireside Tavern Sherborn is a 2-star inn located in Sherborn, within 3 miles of Broadmoor Nature Reserve and Rocky Narrows, and 3 miles from the Charles River, with The Center for Arts in Natick situated 3 miles away.
This accommodation provides complimentary on-site parking, an on-site restaurant, and shared spaces with coffee and tea facilities, offering air conditioning and internet access for guest convenience.

Best Wellesley, MA vacation rentals with air conditioning

A Stylish Stay W/ A Queen Bed, Heated Floors.. #34 - Wellesley, MA
9.1 3 reviews

A Stylish Stay W/ A Queen Bed, Heated Floors.. #34

apartment, Brookline
Apartment listing with an excellent rating of 91% based on 3 reviews. Your accommodation will be located in Brookline.
Facilities and services: a dish washer, a washing machine and a terrace.
A Stylish Stay W/ A Queen Bed, Heated Floors.. #31 - Wellesley, MA
9.2 537 reviews

A Stylish Stay W/ A Queen Bed, Heated Floors.. #31

apartment, Brookline
This Brookline apartment is conveniently located near both Fenway Park and Boston University, making it a great choice for exploring the city's cultural attractions and academic institutions. The apartment has received excellent ratings for cleanliness, location, and overall user experience.
The studio apartment offers 300 square feet of space and can comfortably accommodate two guests. It features a fully equipped kitchen with a dishwasher, a washing machine, a walk-in shower, air conditioning, and heated floors, ensuring a comfortable and convenient stay.
Garden Studio, Access To I-93 To Airport, Tufts U, Hiking & Chevalier Theater. - Wellesley, MA
10 62 reviews

Garden Studio, Access To I-93 To Airport, Tufts U, Hiking & Chevalier Theater.

studio, Medford
This studio apartment is located in Medford, just a short distance from the Mystic River and within easy reach of downtown Boston, Harvard Square, and Tufts University. It has received excellent user ratings, making it a popular choice for travelers.
The studio is spacious at 900 square feet and comfortably accommodates up to 4 guests. It includes modern amenities like air conditioning, internet access, a kitchen with a fridge and microwave, and parking.
A Stylish Stay W/ A Queen Bed, Heated Floors.. #11 - Wellesley, MA
No reviews

A Stylish Stay W/ A Queen Bed, Heated Floors.. #11

apartment, Brookline
Apartment to rent. This accommodation is based in Brookline.
Facilities and services: an iron, a fridge and a dish washer.

Frequently Asked Questions about vacation rentals in Wellesley, MA

  • Which neighborhood in Wellesley, MA should you consider for a vacation rental?

    Wellesley is a small town with a very residential feel, so there aren't really distinct neighborhoods like you might find in a larger city. However, if you want to be close to the downtown area, you might look for a rental near the Wellesley Square, which is the heart of town with shops, restaurants, and the train station. If you prefer a quieter setting, you might consider a rental near the Weston town line, which is a bit more rural.
  • What are the best Airbnb and vacation rentals in Wellesley, MA?

    Near Colleges + Train 2bd 2ba Quiet Entire Home, Gorgeous Super Clean Newly Renovated Modern Colonial and Large & Charming Downtown Wellesley are the most popular Airbnb and vacation rentals in Wellesley, MA among travelers.

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

    Wellesley is great for families! The Hunnewell School playground is a local favorite, and the Wellesley Free Library offers a variety of programs for kids of all ages. The Wellesley Community Center also has a pool and a fitness center, and the town hosts a number of family-friendly events throughout the year, like the annual Wellesley Farmers Market.
  • What are the most popular Airbnbs in Wellesley, MA?

    Among the Airbnbs in Wellesley, MA, Near Colleges + Train 2bd 2ba Quiet Entire Home and Large & Charming Downtown Wellesley are the most popular ones.

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

    Wellesley is a great place to visit year-round, but if you want to enjoy the best weather, you might want to book your rental during the spring or fall. Keep in mind that summer can get pretty crowded, especially around the Fourth of July, and the winter months can be quite cold. If you're flexible, you might find some great deals on rentals during the off-season.
  • What are the best rentals for families and kids in Wellesley, MA?

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

    Wellesley has a few events throughout the year, like the Wellesley Farmers Market, which takes place on Saturdays from June to October. The town also hosts the Wellesley Holiday Stroll in December. You can also check out the events calendar for nearby towns like Weston, Newton, and Natick, which often have fun festivals and events.
  • 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 budget-friendly activities in Wellesley, MA?

    Wellesley is a great place to explore on foot or by bike. You can enjoy the beautiful scenery of the town by taking a walk or bike ride along the Charles River or through the Wellesley College campus. The Wellesley Free Library is also a great place to spend some time, and it's completely free.
  • What are the best restaurants with local dishes in Wellesley, MA?

    Wellesley has a variety of restaurants, but if you're looking for local dishes, you might want to try The Avenue, which has a great selection of New England classics, or The Publick House, which is known for its traditional American fare. For a more casual dining experience, check out The Friendly Toast, which is a popular spot for brunch and breakfast.
  • What are the best walking or cycling routes in Wellesley, MA?

    Wellesley has a great network of walking and biking paths. The Charles River Path is a popular choice for a scenic walk or bike ride, and the town also has a number of parks and trails. The Wellesley College campus is also a great place to explore on foot, and you can find a map of the town's walking and biking paths on the town website.
  • Are there pet-friendly attractions in Wellesley, MA?

    Wellesley is a very dog-friendly town. Many of the town's parks and trails are dog-friendly, and many restaurants have outdoor seating where you can bring your furry friend. The Wellesley Free Library also has a special program for dogs called 'Dog Days at the Library' where you can bring your dog to the library for a storytime session.
  • What are the benefits of choosing a vacation rental in Wellesley, MA?

    Vacation rentals offer more space and privacy than a hotel room, and they can be a great option for families or groups traveling together. Vacation rentals are often located in residential areas, which can provide a more authentic experience of the town. And you can often find vacation rentals that are pet-friendly, which can be a major benefit for travelers with furry companions.

Popular destinations

Find the Best Vacation Rentals with Balconies in Wellesley, MA

Enjoy stunning views from your private terrace when you book one of these vacation rentals in Wellesley, MA.

Vibrant 4br Boston Apt - Balcony, Bathtub, Tv Near I-95 & Pet Friendly 903 - Wellesley, MA
No reviews

Vibrant 4br Boston Apt - Balcony, Bathtub, Tv Near I-95 & Pet Friendly 903

apartment, Boston
Vacation rental. You will be in Boston.
Services and facilities: an iron, free parking and an access for persons with reduced mobility. Take advantage of the terrace in this apartment in Boston.
Sports Lovers, Foodies, Families, And College Visitors Will Feel Right At Home In This Topfloor 4bed, 2bath Tripledecker With Balcony, Fully Equipped Kitchen, Park Views, And Easy Access To Boston. - Wellesley, MA
8.0 2 reviews

Sports Lovers, Foodies, Families, And College Visitors Will Feel Right At Home In This Topfloor 4bed, 2bath Tripledecker With Balcony, Fully Equipped Kitchen, Park Views, And Easy Access To Boston.

apartment, Boston
This 4-bedroom, 2-bathroom apartment in Boston's Dorchester neighborhood offers park views and is located 5 miles from Boston Common, 8 miles from Harvard University, and a 15-25 minute drive to Logan International Airport.
This 1400 square foot rental, accommodating up to 8 guests, features a fully equipped kitchen, in-unit laundry, queen beds in all bedrooms, a private 3rd-floor balcony, and shared backyard access, with convenient access to the MBTA Red Line and Interstate 93.
Cozy 5br Milton Home  Pet-friendly Near I-93 & Blue Hills 14-2 - Wellesley, MA
9.4 9 reviews

Cozy 5br Milton Home Pet-friendly Near I-93 & Blue Hills 14-2

apartment, Milton
This spacious three-story townhouse in Milton, MA, offers easy access to the Blue Hills Reservation and is conveniently located near downtown Boston.
The 1700-square-foot property features five bedrooms, three bathrooms, and can comfortably accommodate up to 15 guests, boasting a fully equipped kitchen, in-unit laundry, and three reserved parking spots; pets are welcome.
Modern & Cozy 3-bedroom Condo Near Downtown - Wellesley, MA
10 10 reviews

Modern & Cozy 3-bedroom Condo Near Downtown

apartment, Boston
This Roxbury in-law suite, less than three miles from downtown Boston, offers easy access to public transportation, major highways, and attractions like Carson Beach and the JFK Presidential Library and Museum.
The 1500-square-foot apartment features three bedrooms, two bathrooms, a fully equipped kitchen with stainless steel appliances, and accommodates up to five guests, with free street parking and complimentary amenities including toiletries and coffee.

Our Favorite Family-Friendly Vacation Rentals in Wellesley, MA

Booking a family-oriented vacation rental in Wellesley, MA keeps you close to top city attractions for a stress-free getaway.

Unique & Peaceful Boston Home, Ideal For 2026 World Cup Visitor, Free Parking - Wellesley, MA
9.4 86 reviews

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

apartment, Boston
This Boston apartment is located in a peaceful area, just 6.3 miles from the Boston Museum of Fine Arts and 6.9 miles from Fenway Park. The apartment consistently receives excellent ratings for cleanliness, location, and overall user experience. The two-bedroom rental comfortably accommodates up to five guests within its 950 square feet. Guests can enjoy a private garden, free parking, and convenient amenities such as a dishwasher, oven, and washer, as well as a terrace, bike parking, and private check-in and check-out.
Modern Massive Large Group 3800sf Mit Harvard Bos - Wellesley, MA
9.5 41 reviews

Modern Massive Large Group 3800sf Mit Harvard Bos

apartment, Somerville
This Somerville apartment is conveniently located near Assembly Row, Harvard University, and Encore Boston Harbor, making it a great choice for travelers who want to be close to the action. It's also situated in a quieter part of East Somerville, offering a peaceful retreat from the city's hustle and bustle. The apartment has received excellent ratings from previous guests, so you can be confident you'll have a comfortable stay.
The spacious apartment features 4 bedrooms and a sofa bed, providing ample space for families or groups of friends. You'll also have access to a fully equipped kitchen, free WiFi, a spa tub, and parking, making your stay easy and enjoyable.
Harvard Charm / Near Boston + New Build - Wellesley, MA
No reviews

Harvard Charm / Near Boston + New Build

apartment, Cambridge
This Wellington-Harrington neighborhood apartment in Cambridge offers exceptional walkability, with Union Square just a 5-minute walk away and Central Square a 15-minute walk, providing convenient access to MIT and Harvard.
This newly renovated, modern 3-level home spans 1250 square feet, featuring 4 bedrooms and 2.5 bathrooms to accommodate up to 8 guests, with amenities including complimentary parking for 2 vehicles, central air conditioning and heating, and a full kitchen.
Newly Renovated Beautiful 3-bed 2-bath Home With Easy Airport Access - Wellesley, MA
9.6 28 reviews

Newly Renovated Beautiful 3-bed 2-bath Home With Easy Airport Access

apartment, Framingham
This Framingham vacation home is conveniently located near Cochituate State Park and Shoppers World, a five-minute drive away.
This three-bedroom, two-bathroom house sleeps seven guests and features a fully equipped kitchen, in-unit laundry, free Wi-Fi, and a private garden with outdoor seating, perfect for families visiting Framingham.

Best Wellesley, MA vacation rentals with parking

Sleek Private Suite Near Bc & Harvard | Parking - Wellesley, MA
9.4 451 reviews

Sleek Private Suite Near Bc & Harvard | Parking

B&B, Boston
Cozy 2br-walk To Tufts & Green Line, Near Boston! - Wellesley, MA
9.4 24 reviews

Cozy 2br-walk To Tufts & Green Line, Near Boston!

apartment, Medford
Charming 1br Apt In Boston With Free Parking - Wellesley, MA
9.6 7 reviews

Charming 1br Apt In Boston With Free Parking

apartment, Boston
Tiny-home Like Living - Wellesley, MA
9.7 78 reviews

Tiny-home Like Living

apartment, Dedham

Popular Luxury Vacation Rentals in Wellesley, MA

Elevate your stay in a luxury vacation rental or Airbnb in Wellesley, MA, featuring high-end finishes and a prime location.

Charming Studio In Boston Brownstone, #44 - Wellesley, MA
9.0 4822 reviews

Charming Studio In Boston Brownstone, #44

studio, Boston

Top Dog-Friendly Vacation Rentals in Wellesley, MA

Discover dog-friendly vacation rentals in Wellesley, MA situated perfectly for city walks and nearby dog parks.

The Verb Hotel - Wellesley, MA
9.4 4871 reviews

The Verb Hotel

hotel, Boston
Comfy & Chic Apartment For 2026 World Cup Free Parking - Wellesley, MA
10 1 review

Comfy & Chic Apartment For 2026 World Cup Free Parking

apartment, Boston
New! 2br Home Metro West - Wellesley, MA
10 6 reviews

New! 2br Home Metro West

apartment, Wayland
Sleek Back Bay Studio - Wellesley, MA
No reviews

Sleek Back Bay Studio

studio, Boston

Top-Rated Vacation Rentals with a Pool in Wellesley, MA

A vacation rental with a pool in Wellesley, MA makes it easy to fit in a proper swim right in the heart of the city.

The Verb Hotel - Wellesley, MA
9.4 4871 reviews

The Verb Hotel

hotel, Boston

Check Out Vacation Rentals with a Hot Tub in Wellesley, MA

These Wellesley, MA city rentals feature private hot tubs, providing the perfect sanctuary after a day of urban exploration.

Spacious Family Home| Perfect For Relocation - Wellesley, MA
10 2 reviews

Spacious Family Home| Perfect For Relocation

apartment, Natick
Spacious And Cozy- Near T-station-quiet Neighborhood! - Wellesley, MA
No reviews

Spacious And Cozy- Near T-station-quiet Neighborhood!

apartment, Malden
©2026 cozycozy.com