Wellesley Holiday Rentals

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Our top choices for Wellesley holiday rentals

Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (631 reviews)
"Great location, Central to all main attractions and great restaurants, food, entertainment. Custom house is fantastic building rich in history. Great place to stay in Boston "
Australia
Antonios
The price is AU$451
includes taxes & fees
25 May - 26 May
Marriott Vacation Club® at Custom House, Boston

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (693 reviews)
"Great location "
Canada
Robert
The price is AU$394
includes taxes & fees
25 May - 26 May
Global Luxury Suites Downtown Boston

Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (283 reviews)
"Good"
South Korea
HYOJUNG
The price is AU$467
includes taxes & fees
24 May - 25 May
Kasa Boston at Fenway

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (32 reviews)
"Charming room, fresh towels, clean!! I would stay here again."
United States
Mary
The price is AU$473
includes taxes & fees
24 May - 25 May
The Chester Hotel

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (212 reviews)
"The rooms are very spacious and clean. I liked the lighting provided as well."
United States
Hayley
The price is AU$519
includes taxes & fees
25 May - 26 May
Charlesgate Suites

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (151 reviews)
"The property is clean and for the money, is a win for the visitor. "
United States
Ramon S
The price is AU$320
includes taxes & fees
24 May - 25 May
Maverick Suites at 400 Columbus Ave

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (376 reviews)
"Wonderful stay, convenient location "
United States
Junhu
The price is AU$282
includes taxes & fees
24 May - 25 May
Temple Place Suites

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (366 reviews)
"Great stay. "
United States
Anna
The price is AU$352
includes taxes & fees
24 May - 25 May
Maverick Suites at 28 Fenway

Symple Live

Symple Live
4.0 star property
Fenway–Kenmore
The price is AU$454
includes taxes & fees
24 May - 25 May
Symple Live

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (116 reviews)
"A phenomenal stay at maverick suites! The location was fantastic, the room was spotless and cozy, and the check-in/out process was a breeze. I’d happily stay here again and recommend to anyone taking a trip to Boston!"
United States
Kendra
The price is AU$317
includes taxes & fees
25 May - 26 May
Maverick Suites at 40 Temple St

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, (168 reviews)
"Great place for a solo business trip. Great location"
United States
Eleazar
The price is AU$350
includes taxes & fees
25 May - 26 May
Maverick Suites at 245 Newbury St

Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
Downtown Boston
The price is AU$591
includes taxes & fees
25 May - 26 May
Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

Primo North End Studio

Primo North End Studio
North End
9.2 out of 10, Wonderful, (14 reviews)
"Great place, amazing location!"
United States
Christopher W.
The price is AU$559
includes taxes & fees
30 May - 31 May
Primo North End Studio

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (282 reviews)
"This is a converted space, not a hotel - I stayed in the top floor with a private bath, and it was clean, quiet, comfy and spacious. Can't ask for more for that price walking distance to the amtrak."
United States
CHRISTOPHER
The price is AU$239
includes taxes & fees
24 May - 25 May
Premier Suites - Bay Village

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$445
includes taxes & fees
30 May - 31 May
Perfect One Bedroom Stay In Downtown Boston!

The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (36 reviews)
"Excellent location, very easy check in process, clean, just as the pictures showed online."
United States
shannon
The price is AU$1,142
includes taxes & fees
25 May - 26 May
The Monty Boston

Prime Central 1brm in North End Boston

Prime Central 1brm in North End Boston
North End
9.6 out of 10, Exceptional, (25 reviews)
"Location was ideal and property was well-kept and organized. Definitely would recommend for future visits."
United States
Taye A.
The price is AU$542
includes taxes & fees
31 May - 1 June
Prime Central 1brm in North End Boston

Boston Financial District 1BR | Walk to anything!

Boston Financial District 1BR | Walk to anything!
Downtown Boston
10.0 out of 10, Exceptional, (1 review)
"The room was great, for what little time we spent in it, it was a really cozy place. The bed was huge, and really comfortable, I loved how much light the place got as well, with the windows. We were slightly off put by the pictures of the place with how incredibly beige the place looked, but I can assure you it looks way better in person lol. The location is great as well, I've never been to a city this walkable, so I'm glad we picked somewhere right in the middle of it, almost every direction...
United States
Kyle
The price is AU$539
includes taxes & fees
24 May - 25 May
Boston Financial District 1BR | Walk to anything!

Back-Bay Upscale Central Condo Bos Common Downtown

Back-Bay Upscale Central Condo Bos Common Downtown
Bay Village
10.0 out of 10, Exceptional, (11 reviews)
"Everything went smoothly with booking, checking in and checking out. Unit was as nice as the description and photos."
United States
Helen C.
The price is AU$1,368
includes taxes & fees
31 May - 1 June
Back-Bay Upscale Central Condo Bos Common Downtown

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.6 out of 10, Excellent, (10 reviews)
"Beautiful place right on historic Newbury Street. I’ll definitely return and I’d highly recommend this apartment."
United States
JEANPAUL
The price is AU$418
includes taxes & fees
25 May - 26 May
Stylish Back Bay Retreat, Steps from Prudential
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$218 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?

Centrally located in the heart of Boston near T: This holiday home rental outside of Wellesley has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 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.