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Wellesley Holiday Rentals

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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, (1,320 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is AU$215
includes taxes & fees
4 Nov - 5 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, (331 reviews)
"Clean hotel. The space was very nice and open, Very accessible to everything I needed"
United States
Krista
The price is AU$427
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, (340 reviews)
"The area was walkable and the room was great!"
United States
Edna
The price is AU$293
includes taxes & fees
15 Nov - 16 Nov
Maverick Suites at 89 Marion
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

4. 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, (676 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is AU$616
includes taxes & fees
13 Nov - 14 Nov
Marriott Vacation Club® at Custom House, Boston
A living room with a grey sofa, two armchairs, a coffee table, and a large painting on the wall.

5. Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Framingham
10.0 out of 10, Exceptional, (10 reviews)
"Very quiet, quaint and so cozy. We’re very satisfied with this property "
United States
roger n.
The price is AU$348
includes taxes & fees
2 Nov - 3 Nov
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

6. 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 AU$377
includes taxes & fees
1 Nov - 2 Nov
The Chester Hotel
A modern kitchen with white cabinetry, a built-in oven, and a dining area with a table and chairs.

7. Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Framingham
9.6 out of 10, Exceptional, (33 reviews)
"Perfect place to stay. Clean and has everything you need. Would recommend anyone to stay here. "
United States
Michelle M.
The price is AU$498
includes taxes & fees
29 Oct - 30 Oct
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

8. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (763 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is AU$391
includes taxes & fees
10 Nov - 11 Nov
Global Luxury Suites Downtown Boston
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

9. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (446 reviews)
"Really pretty well maintained accomodation close to a lot of cool things to do in boston. its also pretty close to the train and bus station which was helpful to get around"
United States
Rakshitha
The price is AU$363
includes taxes & fees
1 Nov - 2 Nov
Maverick Suites at 28 Fenway
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

10. 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 AU$465
includes taxes & fees
3 Nov - 4 Nov
The Concord Hotel
A modern hotel lobby with a seating area, a bar, and a kitchen.

11. Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very good, (258 reviews)
"Wonderful!!"
United States
Huynh
The price is AU$170
includes taxes & fees
1 Nov - 2 Nov
Residences at Solomon Pond
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, (242 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is AU$568
includes taxes & fees
3 Nov - 4 Nov
Charlesgate Suites
Room

13. 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 AU$604
includes taxes & fees
9 Nov - 10 Nov
Symple Live
A spacious room with a wooden floor, a white door, and a large window with a view of a staircase.

14. The Harvard Room conveniently near BC & Harvard

The Harvard Room conveniently near BC & Harvard
Brighton
9.0 out of 10, Wonderful, (40 reviews)
"The stay here was perfect for my wife and me. It is close ( 0.5 miles) to the purple line, even closer (.2 miles) to a bus stop, and close to restaurants and a brewery (Notch).Note: Big Daddy's Pizza is very close.2 miles) and was superb!"
United States
Michael D.
The price is AU$515
includes taxes & fees
26 Oct - 27 Oct
The Harvard Room conveniently near BC & Harvard
A gazebo with a stone barbecue grill and a table with chairs.

15. Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space

Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
Dedham
9.0 out of 10, Wonderful, (71 reviews)
"Our stay was exactly what we needed while vacationing in Boston. Our host was gracious enough to even let us check in early. We had a ton of space and the beds were very comfortable. Would definitely stay again!"
United States
Cortney
The price is AU$333
includes taxes & fees
28 Oct - 29 Oct
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
A row of brick buildings with storefronts, including a bakery and a liquor store.

16. 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 AU$347
includes taxes & fees
15 Nov - 16 Nov
Maverick Suites at 245 Newbury St
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

17. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (374 reviews)
"Great location,"
United States
Rosemary
The price is AU$223
includes taxes & fees
9 Nov - 10 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.

18. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (181 reviews)
"Very well located. Close to two subways and Copeland Square."
Canada
Lorne
The price is AU$301
includes taxes & fees
9 Nov - 10 Nov
Maverick Suites at 400 Columbus Ave
A spacious indoor swimming pool with large windows, modern seating, and a wooden ceiling.

19. 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 AU$447
includes taxes & fees
9 Nov - 10 Nov
Global Luxury Suites East Boston
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

20. 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, (157 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 AU$363
includes taxes & fees
1 Nov - 2 Nov
Maverick Suites at 40 Temple St
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

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

10/10 Excellent
"Well maintained. Wish they had ac"
James 2-night trip
Posted 1 hour ago
The Midtown Hotel MOD Collection by Sonesta

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$215 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?

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.