Wellesley Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Wellesley holiday rentals

Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (333 reviews)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is HK$704
HK$1,304 total
includes taxes & fees
1 Mar - 2 Mar
Temple Place Suites
Lobby lounge

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (665 reviews)
"Everything was great about this place! I will definitely be staying here again!"
United States
Amanda
Global Luxury Suites Downtown Boston
Exterior

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

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
7.8 out of 10, Good, (8 reviews)
"This location is so convenient to BU! Loved how easy check-in was!"
United States
Laura B.
The price is HK$743
HK$1,705 total
includes taxes & fees
2 Mar - 3 Mar
Free Parking at 1 Bed Basement Apt, Near BU & MIT
Iron/ironing board, free WiFi, bed sheets

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (257 reviews)
"We stayed there for four days. The heaters were not working, I got almost sick. And the customer service was awful. I hope you will find better place to stay"
United States
Aziza
The price is HK$851
HK$1,383 total
includes taxes & fees
13 Mar - 14 Mar
Premier Suites - Bay Village
Front of property

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (103 reviews)
"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"
United Kingdom
Jordan Elizabeth Marie
The price is HK$1,831
HK$2,824 total
includes taxes & fees
13 Mar - 14 Mar
Maverick Suites at 40 Temple St
Rooftop terrace

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, (619 reviews)
"I can’t recommend The Custom House enough, it is perfect! The staff are wonderful, it’s very clean and the perfect location to see Boston! "
United States
Melissa
The price is HK$1,523
HK$1,750 total
includes taxes & fees
12 Mar - 13 Mar
Marriott Vacation Club® at Custom House, Boston
Exterior

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, (159 reviews)
"Great location, clean and great 😌 "
United States
Catherine
Maverick Suites at 245 Newbury St
Desk, laptop workspace, free WiFi, bed sheets

Bay Village Suites

Bay Village Suites
2.0 star property
Bay Village
6.6 out of 10, (254 reviews)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites
Front of property

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (337 reviews)
"Good place"
United States
Elijah
The price is HK$739
HK$1,614 total
includes taxes & fees
1 Mar - 2 Mar
Maverick Suites at 28 Fenway
Living area

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (28 reviews)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
United States
kelly
The price is HK$1,169
HK$2,737 total
includes taxes & fees
1 Mar - 2 Mar
The Chester Hotel
1 bedroom, desk, iron/ironing board, WiFi

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 HK$908
HK$1,810 total
includes taxes & fees
1 Mar - 2 Mar
Perfect One Bedroom Stay In Downtown Boston!
Exterior

Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
8.0 out of 10, Very good, (69 reviews)
"Loved how cozy and clean it was. Location was great, near many points of interest. Parking at an extra fee, but plenty of street parking in the area. "
United States
Isaiah Joel Santa
The price is HK$1,758
HK$2,741 total
includes taxes & fees
13 Mar - 14 Mar
Maverick Suites at 402 Columbus Ave
1 bedroom, desk, iron/ironing board, Internet

Cozy Studio Steps from Boston Common and Theaters

Cozy Studio Steps from Boston Common and Theaters
Bay Village
7.4 out of 10, Good, (10 reviews)
"Was clean and the location was perfect for my stay. "
United States
Laurie F.
The price is HK$626
HK$2,079 total
includes taxes & fees
1 Mar - 2 Mar
Cozy Studio Steps from Boston Common and Theaters
Exterior detail

Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!

Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
Beacon Hill
9.6 out of 10, Exceptional, (4 reviews)
"Had a wonderful stay! Beautiful condo in a beautiful neighborhood that is walking distance to the commons."
United States
Grant T.
The price is HK$876
HK$2,284 total
includes taxes & fees
2 Mar - 3 Mar
Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
Interior

Luxury Home located in Back Bay 8min walk to Fewnway Park, close to Boston University, Berklee & MIT

Luxury Home located in Back Bay 8min walk to Fewnway Park, close to Boston University, Berklee & MIT
Fenway–Kenmore
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,713
HK$3,753 total
includes taxes & fees
24 Mar - 25 Mar
Luxury Home located in Back Bay 8min walk to Fewnway Park, close to Boston University, Berklee & MIT
Exterior

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.6 out of 10, Excellent, (7 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 HK$954
HK$2,331 total
includes taxes & fees
2 Mar - 3 Mar
Stylish Back Bay Retreat, Steps from Prudential
Interior

Furnished Apartment near BMC

Furnished Apartment near BMC
3.0 star property
South End
The price is HK$915
HK$2,131 total
includes taxes & fees
1 Mar - 2 Mar
Furnished Apartment near BMC
TV, offices

Perfect location Sleeps 3

Perfect location Sleeps 3
Bay Village
7.8 out of 10, Good, (12 reviews)
"Great location but the unit wasn't exactly what was pictured. Not has updated as the pictures, but it was clean and"
United States
Jaime M.
The price is HK$908
HK$1,776 total
includes taxes & fees
1 Mar - 2 Mar
Perfect location Sleeps 3
TV

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 HK$1,252
HK$2,932 total
includes taxes & fees
22 Mar - 23 Mar
Prime Central 1brm in North End Boston
TV, offices

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 HK$908
HK$1,828 total
includes taxes & fees
8 Mar - 9 Mar
Come Visit Boston and Stay In Our Homey Studio
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wellesley Hotel Reviews

citizenM Boston Back Bay

citizenM Boston Back Bay

10/10 Excellent
"Very clean room, amazing view and kind greeting staff"
Anastasia 1-night trip
Posted 2 days ago
citizenM Boston Back Bay

Find out more about Wellesley

Search for holiday rentals in Wellesley on Expedia! You can easily find your home rentals, villas, holiday apartments in Wellesley using one of the methods below:

  • View our selection of featured holiday rentals in Wellesley
  • Use the map to find apartments and other holiday homes in the Wellesley neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Wellesley while they last

Look no further and take a look at our great range of rental properties in Wellesley!

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?

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino: This holiday home rental outside of Wellesley is located on the waterfront, and has a fireplace, a patio and air conditioning to put you at ease 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. Kick off your shoes and enjoy yourself with a garden and a selection of books.

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?

Wellesley College Botanic Gardens and Charles River 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.