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Holiday Rentals in Wellesley

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Wellesley holiday rentals

An outdoor patio with round tables and chairs, surrounded by green umbrellas.

1. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,310 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is €152
includes taxes & fees
31 Oct - 1 Nov
Crescent Suites Hotel
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

2. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (329 reviews)
"Absolutely gorgeous apartments! Concierge was very friendly!"
United States
Kelly
The price is €277
includes taxes & fees
9 Nov - 10 Nov
Kasa Boston at Fenway
A wooden hallway with a patterned floor leading to a door.

3. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (334 reviews)
"Area is quiet, building is modern, super clean and roomy. Plenty of places to eat within walking distance. Green line is an easy, short walk. Elevator wasn't working, but we were notified ahead of time and we easily managed the one flight of stairs. Would stay here again."
United States
Katerina
The price is €191
includes taxes & fees
9 Nov - 10 Nov
Maverick Suites at 89 Marion
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

4. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (762 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is €238
includes taxes & fees
10 Nov - 11 Nov
Global Luxury Suites Downtown Boston
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

5. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (40 reviews)
"Location was very loud but thank God for earplugs. It was very clean but very old. Very expensive for such a location and room. I always believe in paying for what u get but I paid a lot for 3 nights."
United States
Luda
The price is €245
includes taxes & fees
3 Nov - 4 Nov
The Chester Hotel
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

6. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (442 reviews)
"Great price for the place given the location."
United States
Beenish
The price is €226
includes taxes & fees
1 Nov - 2 Nov
Maverick Suites at 28 Fenway
A modern living room with a round dining table, grey sofas, and large windows offering city views.

7. Furnished Apts near Harvard Stadium

Furnished Apts near Harvard Stadium
2.0 star property
Allston
8.6 out of 10, Excellent, (17 reviews)
"spacious, clean, central location"
United States
Gregory
The price is €266
includes taxes & fees
14 Oct - 15 Oct
Furnished Apts near Harvard Stadium
A row of brick buildings with storefronts, including a bakery and a liquor store.

8. 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, (207 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is €235
includes taxes & fees
9 Nov - 10 Nov
Maverick Suites at 245 Newbury St
A modern hotel lobby with a seating area, a bar, and a kitchen.

9. Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very good, (255 reviews)
"Wonderful!!"
United States
Huynh
The price is €116
includes taxes & fees
2 Nov - 3 Nov
Residences at Solomon Pond
A hotel room with a large bed, two bedside lamps, a headboard, a wall-mounted abstract art piece, and potted plants.

10. Furnished Apartment Near Longwood

Furnished Apartment Near Longwood
3.0 star property
North Brookline
8.2 out of 10, Very good, (12 reviews)
"Great place, clean, well maintained and centrally located. Excellent and timely communication."
United States
Mike Shang-Yu
Furnished Apartment Near Longwood
Room

11. Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (28 reviews)
"Great location. Exactly as pictured."
United States
Erica
The price is €376
includes taxes & fees
9 Nov - 10 Nov
Symple Live
A modern hotel room with a bed, a desk, a sofa, and a dining area.

12. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (241 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is €361
includes taxes & fees
14 Oct - 15 Oct
Charlesgate Suites
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

13. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
8.0 out of 10, Very good, (156 reviews)
"Great property in a great location. Tons of food options nearby. Walking distance to Target and Whole Foods. Easy access to the Blue line. The neighborhood was quiet and clean. Boston common is just a block away. Definitely would stay again and highly recommend."
United States
TommyWallace
The price is €226
includes taxes & fees
1 Nov - 2 Nov
Maverick Suites at 40 Temple St
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

14. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (34 reviews)
"Great location, great Apartment"
United States
Carla Patricia
The price is €315
includes taxes & fees
2 Nov - 3 Nov
The Concord Hotel
A spacious indoor swimming pool with large windows, modern seating, and a wooden ceiling.

15. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (213 reviews)
"Cozy, comfy and cute✨. Would def rent again❤️"
United States
Erica
The price is €278
includes taxes & fees
9 Nov - 10 Nov
Global Luxury Suites East Boston
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

16. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (367 reviews)
"Great location,"
United States
Rosemary
The price is €146
includes taxes & fees
2 Nov - 3 Nov
Premier Suites - Bay Village
A white table with a vase of white orchids, a white chair, and a view of a cityscape through a window with a black frame.

17. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (178 reviews)
"Well located"
United States
Evelyn
The price is €188
includes taxes & fees
9 Nov - 10 Nov
Maverick Suites at 400 Columbus Ave
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

18. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (506 reviews)
"Great location, good value and comfortable beds"
United States
Deborah
The price is €156
includes taxes & fees
3 Nov - 4 Nov
Temple Place Suites
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

19. 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, (675 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is €507
includes taxes & fees
8 Nov - 9 Nov
Marriott Vacation Club® at Custom House, Boston
A hotel room with a bed, a desk, a lamp, a potted plant, and large windows with blinds.

20. Furnished Apartment near BMC

Furnished Apartment near BMC
3.0 star property
South End
5.6 out of 10, (4 reviews)
"I loved this apartment. It was perfect for what we needed. I only gave four stars because the apartment could use a little love and updating, and that may be important to some people. It was not for me. We were just over 2 miles away from Mass General where my husband was having an operation. It had a full kitchen, 1 1/2 baths, and was surprisingly quiet. The description of the apartment was clear there was no parking space associated with the apartment; however, I found that every night...
United States
Christine
The price is €290
includes taxes & fees
14 Oct - 15 Oct
Furnished Apartment near BMC
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

Hyatt Regency Boston

Hyatt Regency Boston

10/10 Excellent
"We loved our stay here. It is right down the block from the show we saw and felt safe walking to and from. Lots of little shops and restaurants near by. Our bonus gifts from being an Expedia member were a nice touch too. Staff went above and beyond, the room was lovely and I would not hesitate to stay here again!"
Hannah 1-night trip
Posted less than an hour ago
Hyatt Regency Boston

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, apart-hotels, 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 €146 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?

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking: This holiday home rental outside of Wellesley has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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 Gillette Stadium.

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.