Wellesley Holiday Rentals

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Our top choices for Wellesley holiday rentals

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (346 reviews)
"Wonderful stay, convenient location "
United States
Junhu
The price is AU$272
includes taxes & fees
8 Apr - 9 Apr
Temple Place Suites

Free Parking at 1 Bed Basement Apt, Near BU & MIT

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.0 out of 10, Very good, (11 reviews)
"Amazing location for the price. Check-in was super easy with clear instructions. Free parking was such a great perk for Boston. As for the house, despite a few visual damages (and 2 lightbulbs for the lamps not working), there was not much to complain about. Would recommend "
United States
Mai
The price is AU$318
includes taxes & fees
12 Apr - 13 Apr
Free Parking at 1 Bed Basement Apt, Near BU & MIT

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (341 reviews)
"Clean"
United States
Kristin
The price is AU$317
includes taxes & fees
14 Apr - 15 Apr
Maverick Suites at 28 Fenway

Perfect North End Studio

Perfect North End Studio
North End
9.6 out of 10, Exceptional, (50 reviews)
"Host was very helpful and accommodating throughout our whole trip. The place had everything we needed for the weekend. Great location and walking distance to lots of great restaurants and coffee shops."
United States
Matthew M.
The price is AU$757
includes taxes & fees
17 Apr - 18 Apr
Perfect North End Studio

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (262 reviews)
"AMAZING!!! Do NOT listen to all of the negative reviews. When I first found this listing I was really unsure because there was so many bad reviews. I took a chance and booked anyway. The stay was phenomenal. Check in was super easy and the company/host was very responsive. Very close to train station as well. They sent text messages and even let us know the room was ready for check in around 2pm instead of waiting until 4pm check in. The room was super clean and nice. No issues with anything....
United States
Amaya
The price is AU$246
includes taxes & fees
7 Apr - 8 Apr
Premier Suites - Bay Village

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (106 reviews)
"Very quiet, great location. "
United States
Cole
The price is AU$370
includes taxes & fees
7 Apr - 8 Apr
Maverick Suites at 40 Temple St

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (136 reviews)
"I couldn’t quite get the plug in stove to work. But overall it was an alright stay!!"
United States
Myah
The price is AU$304
includes taxes & fees
7 Apr - 8 Apr
Maverick Suites at 400 Columbus Ave

Cozy Studio Steps from Boston Common and Theaters

Cozy Studio Steps from Boston Common and Theaters
Bay Village
7.8 out of 10, Good, (11 reviews)
"Was clean and the location was perfect for my stay. "
United States
Laurie F.
The price is AU$386
includes taxes & fees
8 Apr - 9 Apr
Cozy Studio Steps from Boston Common and Theaters

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (29 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is AU$553
includes taxes & fees
7 Apr - 8 Apr
The Chester Hotel

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very good, (161 reviews)
"Great location, clean and great 😌 "
United States
Catherine
The price is AU$366
includes taxes & fees
12 Apr - 13 Apr
Maverick Suites at 245 Newbury St

Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
The price is AU$683
includes taxes & fees
21 Apr - 22 Apr
Beautiful 1BR near Fenway Park + Kenmore!

King Bed Loft in the Heart of Downtown Boston

King Bed Loft in the Heart of Downtown Boston
Downtown Boston
10.0 out of 10, Exceptional, (38 reviews)
"It was my first time staying here, and the room was very clean and fresh. The staff were extremely friendly and helpful, and the facilities were perfect. I will definitely stay here again, and I highly recommend it to anyone."
Japan
MINEKI
The price is AU$650
includes taxes & fees
26 Apr - 27 Apr
King Bed Loft in the Heart of Downtown Boston

Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
9.2 out of 10, Wonderful, (5 reviews)
"Would stay again"
United States
mark p.
The price is AU$401
includes taxes & fees
7 Apr - 8 Apr
Studio Awaits Your Next Stay!

Primo North End Studio

Primo North End Studio
North End
9.2 out of 10, Wonderful, (13 reviews)
"Great place, amazing location!"
United States
Christopher W.
The price is AU$613
includes taxes & fees
21 Apr - 22 Apr
Primo North End Studio

Furnished Apartment near BMC

Furnished Apartment near BMC
3.0 star property
South End
6.0 out of 10, (1 review)
The price is AU$487
includes taxes & fees
7 Apr - 8 Apr
Furnished Apartment near BMC

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (203 reviews)
"New spot for us in South Bay. Convenient and easy with easy walk to Commonwealth and restaurants of Newbury"
United States
Brian
The price is AU$537
includes taxes & fees
8 Apr - 9 Apr
Charlesgate Suites

Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!
Downtown Boston
8.6 out of 10, Excellent, (18 reviews)
"Came to Boston to take a few college tours and this was a pretty central location. This property was also very close to several other places we were hoping to see while in town. Communication was great and check in was seamless. The property was clean and perfect for our stay. "
United States
elena d.
The price is AU$463
includes taxes & fees
11 Apr - 12 Apr
Perfect One Bedroom Stay In Downtown Boston!

Come Visit Boston and Stay In Our Homey Studio

Come Visit Boston and Stay In Our Homey Studio
Downtown Boston
8.8 out of 10, Excellent, (3 reviews)
"Great central location! Tiny but super !would come back . Great food , bars, brewery , breakfast at our doorstep. By the park too!"
United States
Dean and Courtenay M.
The price is AU$451
includes taxes & fees
12 Apr - 13 Apr
Come Visit Boston and Stay In Our Homey Studio

North End Entire House

North End Entire House
North End
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful home in the heart of the north end. We had a wonderful stay!"
United States
Kerry y.
The price is AU$736
includes taxes & fees
12 Apr - 13 Apr
North End Entire House

Gorgeous Beacon Hills Studio next to State house

Gorgeous Beacon Hills Studio next to State house
Beacon Hill
9.8 out of 10, Exceptional, (33 reviews)
"We had a great stay and host was welcoming and responsive. Thanks!"
United States
Eric M.
The price is AU$558
includes taxes & fees
27 Apr - 28 Apr
Gorgeous Beacon Hills Studio next to State house
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wellesley Hotel Reviews

Find out more about Wellesley

Everything you need to know about Wellesley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wellesley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wellesley holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Wellesley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wellesley. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wellesley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wellesley holiday rentals we have selected for you start as low as AU$230 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Wellesley rentals

At Expedia, we put the best Wellesley holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wellesley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wellesley holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wellesley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Wellesley?

Yes, there are holiday rentals in Wellesley close to Massachusetts Horticultural Society's Gardens at Elm Bank, or you can select a more secluded option if you're looking for a relaxing stay. Wellesley is known for its university setting and basketball games. Make sure you have time to check out the gardens while you're in the area.

What are some of the best holiday rentals that Wellesley has to offer?

Spacious, New Renovation | Near T: This holiday home rental outside of Wellesley is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Wellesley?

Choose from 12 Expedia holiday rentals in Wellesley for a memorable holiday.

What can I see and do in Wellesley?

Charles River and Wellesley College Botanic Gardens are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Massachusetts Horticultural Society's Gardens at Elm Bank. Other popular places to visit in the area include Fenway Park and Harvard Square.

What are holiday rentals like in Wellesley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Wellesley. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a small group gathering.