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 NZ$653
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, (691 reviews)
"The property is located close to a T station and right at the edge of Chinatown so there's a lot of restaurants and bakeries nearby. We love the apartment's high ceiling making the place feel more spacious. The property is clean and the kitchen well stocked with plates and cups. Overall a very enjoyable stay."
United States
Annie
The price is NZ$417
includes taxes & fees
31 May - 1 June
Global Luxury Suites Downtown Boston

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (210 reviews)
"The rooms are very spacious and clean. I liked the lighting provided as well."
United States
Hayley
The price is NZ$747
includes taxes & fees
31 May - 1 June
Charlesgate Suites

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, (167 reviews)
"Great place for a solo business trip. Great location"
United States
Eleazar
The price is NZ$592
includes taxes & fees
31 May - 1 June
Maverick Suites at 245 Newbury St

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (113 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 NZ$592
includes taxes & fees
19 May - 20 May
Maverick Suites at 40 Temple St

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (276 reviews)
"Yes and clean"
United States
Sindy
The price is NZ$319
includes taxes & fees
19 May - 20 May
Premier Suites - Bay Village

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (147 reviews)
"The property is clean and for the money, is a win for the visitor. "
United States
Ramon S
The price is NZ$433
includes taxes & fees
12 May - 13 May
Maverick Suites at 400 Columbus Ave

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (360 reviews)
"Great stay. "
United States
Anna
The price is NZ$537
includes taxes & fees
17 May - 18 May
Maverick Suites at 28 Fenway

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 NZ$1,589
includes taxes & fees
25 May - 26 May
The Monty Boston

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.4 out of 10, Very good, (30 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is NZ$609
includes taxes & fees
18 May - 19 May
The Chester Hotel

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
3.0 star property
Lynn
The price is NZ$691
includes taxes & fees
17 May - 18 May
Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston
2.5 star property
Everett
8.6 out of 10, Excellent, (14 reviews)
"Nice spot"
United States
Kimberly
The price is NZ$464
includes taxes & fees
12 May - 13 May
Furnished Apartments near Encore Boston

Furnished Apts near Harvard Stadium

Furnished Apts near Harvard Stadium
2.0 star property
Allston
8.8 out of 10, Excellent, (12 reviews)
"Great property. Very clean and spacious. Easy 15 minutes walk to Harvard. Easy check in and check out process"
United States
Tho
The price is NZ$498
includes taxes & fees
12 May - 13 May
Furnished Apts near Harvard Stadium

Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
7.8 out of 10, Good, (71 reviews)
"Apartment has everything you need with a great location. Checkin was easy and rooms were very clean. "
United States
Clodagh
The price is NZ$527
includes taxes & fees
19 May - 20 May
Maverick Suites at 402 Columbus Ave

Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (283 reviews)
"Very nice and clean room, excellent location"
United States
Diana
The price is NZ$445
includes taxes & fees
19 May - 20 May
Maverick Suites at 89 Marion

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,193 reviews)
"Excellent stay as always, my home away from home when traveling in the area."
United States
Sean
The price is NZ$257
includes taxes & fees
31 May - 1 June
Crescent Suites Hotel

Enchanting Hidden Door Escape

Enchanting Hidden Door Escape
2.0 star property
Stoneham
The price is NZ$1,212
includes taxes & fees
18 May - 19 May
Enchanting Hidden Door Escape

Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (188 reviews)
"Perfect location, professional staff, great parking arrangement "
United States
Joli
The price is NZ$461
includes taxes & fees
24 May - 25 May
Global Luxury Suites East Boston

Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very good, (238 reviews)
"Professional and courteous staff and i formative. Room was clean and well stocked with utensils and toiletries. Best olace ive been to so far. "
United States
Joan
The price is NZ$191
includes taxes & fees
28 May - 29 May
Residences at Solomon Pond

Gillette Soccer Event HQ < 1 Mi to Patriot Place!

Gillette Soccer Event HQ < 1 Mi to Patriot Place!
3.0 star property
Foxborough
The price is NZ$2,193
includes taxes & fees
12 May - 13 May
Gillette Soccer Event HQ < 1 Mi to Patriot Place!
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 favorite 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 depends 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 NZ$257 per night. Entering your travel dates in the search wizard you might find 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.