Wellesley holiday homes

We found 2,922 holiday rentals — enter your dates for availability
Discover a selection of 12 homes and other holiday rentals in Wellesley that are perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as Wi-Fi and parking. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Wellesley

Showing deals for:18 Dec - 25 Dec

Private kitchen
Interior
Interior
Exceptional
(96 reviews)

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Boston

8% off
NZ$19,266
for 7 nights, 1 home
NZ$2,752 per night
includes taxes & fees
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Bar Counter
Bedroom 1 (Level 2): 1 King bed + ensuite full bath
Living Room
Living Room
Exceptional
(5 reviews)

Lux Colonial Home: Hot tub, Game Room, Home Theatre, Karaoke

Framingham

12% off
NZ$7,398
for 7 nights, 1 home
NZ$1,057 per night
includes taxes & fees
Lux Colonial Home: Hot tub, Game Room, Home Theatre, Karaoke
Private kitchen
Exterior detail
Outdoor dining
Interior
Exceptional
(6 reviews)

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

Newton

9% off
NZ$31,255
for 7 nights, 1 home
NZ$4,465 per night
includes taxes & fees
Luxury Tuscan style villa just few miles from downtown Boston .Newton Reg #24-17
Room
Living area
Private kitchen
Room
Exceptional
(14 reviews)

Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station

Boston

20% off
NZ$9,149
for 7 nights, 1 home
NZ$1,307 per night
includes taxes & fees
Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station
Private kitchen
Terrace/patio
Exterior detail
Room
Exceptional
(33 reviews)

Lovely Studio Walk to Wellesley and Babson College

Wellesley

8% off
NZ$3,756
for 7 nights, 1 home
NZ$537 per night
includes taxes & fees
Lovely Studio Walk to Wellesley and Babson College
Room
Interior
Outdoor private space
Living area
Exceptional
(49 reviews)

World Cup 4BR Near Downtown Boston Parking & 1-Min Walk to Train

Boston

9% off
NZ$7,435
for 7 nights, 1 apartment
NZ$1,062 per night
includes taxes & fees
World Cup 4BR Near Downtown Boston Parking & 1-Min Walk to Train
Interior
Living area
Private kitchen
Interior
Wonderful
(19 reviews)

Newly Renovated Modern Retreat l Near T

Boston

5% off
NZ$7,228
for 7 nights, 1 apartment
NZ$1,033 per night
includes taxes & fees
Newly Renovated Modern Retreat l Near T
Exterior detail
Property grounds
Interior
Sitting room
Exceptional
(20 reviews)

Charming 2-bedroom house with a hidden garden in lovely Cambridge.

Cambridge

7% off
NZ$5,913
for 7 nights, 1 home
NZ$845 per night
includes taxes & fees
Charming 2-bedroom house with a hidden garden in lovely Cambridge.
Room
Interior
Bathroom
Interior
Exceptional
(21 reviews)

Modern home-like 3BR2BA Retreat/Minutes to T

Boston

8% off
NZ$7,340
for 7 nights, 1 home
NZ$1,049 per night
includes taxes & fees
Modern home-like 3BR2BA Retreat/Minutes to T
Interior
Private kitchen
Dining
Living area
Wonderful
(24 reviews)

Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2

Boston

8% off
NZ$6,248
for 7 nights, 1 apartment
NZ$893 per night
includes taxes & fees
Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2
Room
Spacious 4 BR home for groups. Perfect for relaxing and gathering together
Outdoor dining
Private kitchen
Exceptional
(12 reviews)

4BR Near Downtown Boston Private Driveway Parking & 1-Min Walk to Train

Boston

8% off
NZ$7,987
for 7 nights, 1 apartment
NZ$1,141 per night
includes taxes & fees
4BR Near Downtown Boston Private Driveway Parking & 1-Min Walk to Train
Private kitchen
Living area
Living area
Outdoor dining
Exceptional
(42 reviews)

Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH

Boston

8% off
NZ$9,570
for 7 nights, 1 apartment
NZ$1,367 per night
includes taxes & fees
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Dining
Interior
Interior
Private kitchen
Very good
(6 reviews)

6BR3BA w Parking Near T I Foosball & Family Space

Boston

8% off
NZ$8,659
for 7 nights, 1 apartment
NZ$1,237 per night
includes taxes & fees
6BR3BA w Parking Near T I Foosball & Family Space
Interior
Exterior detail
Exterior detail
Living area
Exceptional
(8 reviews)

3-bedroom 2 baths beautiful victorian with WiFi, AC

Boston

8% off
NZ$8,057
for 7 nights, 1 apartment
NZ$1,151 per night
includes taxes & fees
3-bedroom 2 baths beautiful victorian with WiFi, AC
Living area
Living area
Dining
Tufts campus is just a 1 minute walk away with beautiful areas for sitting
Exceptional
(11 reviews)

Comfy, Stylish Apt. Near Uni's, Driveway

Somerville

8% off
NZ$6,447
for 7 nights, 1 apartment
NZ$921 per night
includes taxes & fees
Comfy, Stylish Apt. Near Uni's, Driveway
Room
Living area
Dining
Living area
Exceptional
(78 reviews)

The Pistachio Room at TPH - Boston

Boston

7% off
NZ$1,727
for 7 nights, 1 room
NZ$247 per night
includes taxes & fees
The Pistachio Room at TPH - Boston
Laundry in property
Private kitchen
Overview
Room
Exceptional
(52 reviews)

A beautiful 3BR Apartment near Harvard and MIT.

Cambridge

6% off
NZ$5,232
for 7 nights, 1 apartment
NZ$747 per night
includes taxes & fees
A beautiful 3BR Apartment near Harvard and MIT.
Living area
Room
Interior
Interior
Exceptional
(45 reviews)

A Cozy 5BR Apartment near Harvard Square and MIT

Cambridge

5% off
NZ$7,166
for 7 nights, 1 apartment
NZ$1,024 per night
includes taxes & fees
A Cozy 5BR Apartment near Harvard Square and MIT
Room
Interior
Private kitchen
Interior
Exceptional
(28 reviews)

3BR2BA Retreat - 2min to Savin Hill Station

Boston

8% off
NZ$6,973
for 7 nights, 1 apartment
NZ$996 per night
includes taxes & fees
3BR2BA Retreat - 2min to Savin Hill Station
Room
Dining
Living area
Living area
Very good
(10 reviews)

3-bedroom apartment in charming Boston/ Near Train

Boston

8% off
NZ$6,290
for 7 nights, 1 apartment
NZ$899 per night
includes taxes & fees
3-bedroom apartment in charming Boston/ Near Train
Private kitchen
Interior
Outdoor dining
Living area
Exceptional
(29 reviews)

Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train

Boston

7% off
NZ$3,060
for 7 nights, 1 apartment
NZ$437 per night
includes taxes & fees
Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train
Located on floor 2 of a classic Boston 1860's Rowhouse
Living area
Interior
Entrance/steps to apartment. Please note, steps required
Exceptional
(89 reviews)

Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!

Boston

8% off
NZ$2,765
for 7 nights, 1 apartment
NZ$395 per night
includes taxes & fees
Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!
Living area
Room
Dining
Private kitchen
Exceptional
(23 reviews)

Cozy Cambridge 2bed 2bath w/ Patio & Parking Pass

Cambridge

15% off
NZ$4,517
for 7 nights, 1 home
NZ$645 per night
includes taxes & fees
Cozy Cambridge 2bed 2bath w/ Patio & Parking Pass
Exterior
Interior
Room
Interior
Wonderful
(14 reviews)

Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

Winthrop

8% off
NZ$2,362
for 7 nights, 1 apartment
NZ$337 per night
includes taxes & fees
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

  • 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

Find the perfect holiday 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 Gillette Stadium are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Wellesley

Do you want to discover attractions to visit during your stay? Venture out of your cosy holiday rental and experience everything that Wellesley has to offer. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • New England Aquarium (13.1 mi / 21.1 km)
  • Encore Boston Harbor (13.3 mi / 21.3 km)
  • Massachusetts Horticultural Society's Gardens at Elm Bank (1.6 mi / 2.6 km)
  • The Skating Club of Boston (9.1 mi / 14.6 km)
  • Samuel Adams Brewery (9.8 mi / 15.7 km)
  • Franklin Park Zoo (10.4 mi / 16.7 km)

Exploring the natural features in Wellesley

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Wellesley is a great place to get outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Chestnut Hill Reservoir (7.4 mi / 11.9 km)
  • Arnold Arboretum (8.6 mi / 13.9 km)

Transport 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 centre. 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 travelling by train, Wellesley Square Station, Wellesley Hills Station and Wellesley Farms Station are the main stations in the city.

Frequently asked questions

What is the best area to stay in Wellesley when booking a holiday rental?
When considering a holiday rental in Wellesley, Massachusetts, the best area to stay in is the charming centre of Wellesley itself. This locality is not only picturesque but also offers easy access to a variety of amenities, making it a convenient choice for visitors. The area is characterised by its quaint shops, delightful cafés, and a friendly community atmosphere.One of the highlights of staying in Wellesley is the proximity to Wellesley College, an esteemed institution with beautiful grounds and architecture that are worth exploring. Additionally, the Wellesley Town Forest provides a lovely natural retreat, offering walking trails and serene spots for relaxation.In terms of holiday rentals, the town offers a diverse selection of properties, from cosy cottages to spacious family homes, ensuring that there's something to suit every taste and budget.
What is the most popular type of holiday rental accomodation in Wellesley?
In Wellesley, holiday houses are the most popular type of holiday rental, with around 28 available throughout the area. These spacious homes typically feature multiple bedrooms, fully equipped kitchens, and private gardens, making them ideal for families or groups seeking comfort and convenience. Additionally, there are several apartments and condos that offer a more compact living space, often including amenities such as laundry facilities and communal areas.
Are there any family house rentals in Wellesley?
In Wellesley, Massachusetts, there are several family-friendly house rentals available that cater to a variety of needs. This charming town features lovely neighbourhoods, including the picturesque Wellesley Hills and the vibrant Wellesley Square. Many properties offer spacious living areas, superb for family gatherings, alongside fully equipped kitchens that make meal preparation a breeze.Visitors can expect amenities such as outdoor spaces for children to play and even some homes featuring private gardens or patios for relaxation. Proximity to local parks, such as Wellesley College Botanic Gardens, provides additional opportunities for outdoor activities and exploration, while the nearby shops and restaurants in Wellesley Square add convenience to your stay.
Are there pet-friendly house rentals in Wellesley?
In Wellesley, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these homes are located in tranquil residential neighbourhoods, offering a peaceful retreat while still being close to local amenities. Expect to find properties equipped with spacious backyards, ideal for pets to roam freely, as well as modern amenities such as fully equipped kitchens, comfortable living spaces, and sometimes even features like outdoor patios or decks for relaxation.Wellesley is also home to beautiful parks, such as the popular Wellesley College Botanic Gardens and the scenic Morses Pond, both of which provide lovely settings for walks and outdoor activities with your furry companions. The area's charming downtown offers pet-friendly cafes and shops, making it a delightful spot for both you and your pet to explore.
Are there any remote work holiday rentals in Wellesley?
In Wellesley, Massachusetts, there are plenty of remote work-friendly holiday rentals available, with around 32 options for those seeking a productive stay. The town's charming atmosphere and proximity to Boston make it an attractive location for remote workers. Many of these properties come equipped with essential amenities such as high-speed internet, Wi-Fi, and dedicated workspaces, including desks in various accommodations, ensuring a comfortable and efficient work environment.Wellesley is known for its beautiful parks and vibrant community, with easy access to local cafes and shops that are great for taking breaks or enjoying a change of scenery. Additionally, the nearby Wellesley College offers picturesque walking paths, ideal for a refreshing stroll during work breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Wellesley?
In Wellesley, popular rental amenities include decks or patios for enjoying the pleasant New England weather, kitchens that allow guests to prepare their own meals, and onsite parking for convenience. Many rentals also feature coffee and tea makers for a quick morning brew and desks for those needing a workspace during their stay.
When is the best time to visit Wellesley for a holiday rental?
April is the most popular month to visit Wellesley, as it falls within the peak season from March to May. During this time, the town comes alive with blooming flowers and mild temperatures, making it superb for outdoor activities and leisurely strolls through its picturesque streets. Many visitors enjoy exploring local parks, such as Elm Bank Reservation, where the vibrant colours of spring create a stunning backdrop for a day out.While the peak season offers a lively option, it's worth noting that the climate during April typically ranges from about 5 to 15 degrees Celsius, providing comfortable conditions for sightseeing and enjoying the scenic beauty of the area. This is an ideal time to take in the charm of Wellesley's historic architecture and perhaps indulge in a picnic by the lake.For those seeking a more budget-friendly option, consider a visit in November. While this month is quieter, it presents a unique opportunity to experience Wellesley's serene beauty as the fall foliage begins to fade and the town prepares for winter. This off-peak time allows for a more relaxed pace, superb for exploring local shops and enjoying the community's welcoming atmosphere.
What are the top attractions in Wellesley?
In Wellesley, Massachusetts, visitors can enjoy a variety of attractions that showcase the town's charm and natural beauty. The Wellesley College campus, renowned for its stunning grounds and beautiful architecture, is a must-visit, particularly the impressive Green Hall and the picturesque lake that surrounds the campus. The college also hosts the renowned Wellesley College Botanic Gardens, offering serene walking paths and diverse plant collections.For outdoor enthusiasts, the nearby Centennial Park provides ample space for picnics and leisurely strolls, while the Wellesley Town Forest features trails for hiking and nature walks, ideal for those looking to explore the local flora and fauna. The charming Wellesley Square is great for shopping and dining, featuring a mix of boutique stores and cafés, making it a lovely spot to relax and soak in the local atmosphere.
Are all fees included in the Wellesley holiday homes prices shown on Bookabach?
Bookabach 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 Wellesley holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Wellesley 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 Wellesley holiday homes?
You can find great discounts on holiday homes in Wellesley on Bookabach, 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 Wellesley holiday home booking on Bookabach?
To find Wellesley holiday rentals with free cancellation, just use Bookabach'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, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Wellesley?
A long-stay holiday home in Wellesley 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 Bookabach?
Bookabach'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 Wellesley holiday home?
Book your Wellesley 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Wellesley?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Wellesley to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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