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Wellesley Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Wellesley holiday rentals

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, (641 reviews)
"Best hotel for stay in Boston!"
United States
Frank
The price is HK$2,525
HK$2,902 total
includes taxes & fees
19 Jul - 20 Jul
Marriott Vacation Club® at Custom House, Boston
Lobby lounge

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (718 reviews)
"Clean room, great staff and fantastic location for a reasonable price."
United States
April
The price is HK$1,308
HK$2,444 total
includes taxes & fees
30 Jul - 31 Jul
Global Luxury Suites Downtown Boston
Lobby

Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (294 reviews)
"Amazing location we loved it"
United States
MARLYN
The price is HK$2,462
HK$3,641 total
includes taxes & fees
19 Jul - 20 Jul
Kasa Boston at Fenway
Living area

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (34 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is HK$1,256
HK$2,434 total
includes taxes & fees
16 Jul - 17 Jul
The Chester Hotel
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, (184 reviews)
"Great location and easy to get into. Appreciated the cheaper cost, as I really just need a place to sleep. It served it's purpose well and walking distance to many great locations."
United States
Jason
The price is HK$1,262
HK$2,171 total
includes taxes & fees
16 Jul - 17 Jul
Maverick Suites at 245 Newbury St
Premium bedding, desk, iron/ironing board, free WiFi

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (218 reviews)
"The rooms are very spacious and clean. I liked the lighting provided as well."
United States
Hayley
The price is HK$1,897
HK$3,532 total
includes taxes & fees
19 Jul - 20 Jul
Charlesgate 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, (387 reviews)
"Everything was perfect"
United States
Catherine
The price is HK$1,238
HK$2,189 total
includes taxes & fees
20 Jul - 21 Jul
Maverick Suites at 28 Fenway
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, (305 reviews)
"Great location and well maintained"
United States
EDDIE
The price is HK$811
HK$1,338 total
includes taxes & fees
19 Jul - 20 Jul
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
7.8 out of 10, Good, (130 reviews)
"Location Location Location"
United States
Rebecca
The price is HK$1,764
HK$2,748 total
includes taxes & fees
16 Jul - 17 Jul
Maverick Suites at 40 Temple St
42-inch TV with satellite channels

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (158 reviews)
"Great location!"
United States
Kevin
The price is HK$1,293
HK$2,027 total
includes taxes & fees
16 Jul - 17 Jul
Maverick Suites at 400 Columbus Ave
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, (405 reviews)
"Wonderful stay at this property. Location was excellent, and the host is very quick and responsive to answer any questions you may have."
United States
Jennifer
The price is HK$945
HK$1,582 total
includes taxes & fees
19 Jul - 20 Jul
Temple Place Suites
Iron/ironing board, free WiFi

The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (2 reviews)
"There was very little loud construction outside the window as well as in the building before 8:30 am. The place was cute and relatively clean. Owners gave us a discount for the noise"
United States
Sara
The price is HK$1,785
HK$3,043 total
includes taxes & fees
2 Aug - 3 Aug
The Concord Hotel
1 bedroom, desk, iron/ironing board, WiFi

Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
8.6 out of 10, Excellent, (7 reviews)
"Would stay again"
United States
mark p.
The price is HK$1,011
HK$1,943 total
includes taxes & fees
16 Jul - 17 Jul
Studio Awaits Your Next Stay!
2 bedrooms, desk, iron/ironing board, WiFi

Free Parking 2 Bed 1 Bath Steps from BU/Kenmore

Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
Fenway–Kenmore
8.0 out of 10, Very good, (5 reviews)
"Welcoming host, very responsive"
United States
Matthew G.
The price is HK$956
HK$2,523 total
includes taxes & fees
19 Jul - 20 Jul
Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (9 reviews)
"Looks like a brand new unit - very tastefully done. Immaculately clean. Stocked with everything you might need. Easy check in and great location - walkable to BU and Fenway."
United States
Kimberley
The price is HK$1,873
HK$3,009 total
includes taxes & fees
3 Aug - 4 Aug
Symple Live
Exterior

Rare FREE Parking • Private North End Gem • Prime Location

Rare FREE Parking • Private North End Gem • Prime Location
North End
9.6 out of 10, Exceptional, (61 reviews)
"Great place and a great location"
United States
Thomas M.
The price is HK$1,740
HK$3,637 total
includes taxes & fees
23 Jul - 24 Jul
Rare FREE Parking • Private North End Gem • Prime Location
1 bedroom, desk, iron/ironing board, WiFi

Downtown Crossing, Affordable Stay, Book Now!

Downtown Crossing, Affordable Stay, Book Now!
Downtown Boston
6.2 out of 10, (14 reviews)
"Great location!"
United States
Sean
The price is HK$1,231
HK$2,247 total
includes taxes & fees
19 Jul - 20 Jul
Downtown Crossing, Affordable Stay, Book Now!
Exterior

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

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.6 out of 10, Excellent, (26 reviews)
"Friendly hosts"
United States
Jan
The price is HK$745
HK$1,673 total
includes taxes & fees
19 Jul - 20 Jul
Free Parking at 1 Bed Basement Apt, Near BU & MIT
Exterior

Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
10.0 out of 10, Exceptional, (4 reviews)
"It was a great stay!"
United States
Adina S.
The price is HK$854
HK$2,286 total
includes taxes & fees
10 Aug - 11 Aug
Light-filled Studio | Back Bay
Exterior

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
10.0 out of 10, Exceptional, (1 review)
"Host was very communicative. The apartment was very clean and spacious and the location was fantastic! A lot of things in walking distance and train stop nearby for getting to other parts of the city was convenient. I would highly recommend this host and their space! Thank you for your hospitality! Would love to come back."
United States
Rachael M.
The price is HK$1,273
HK$3,088 total
includes taxes & fees
20 Jul - 21 Jul
Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
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 Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"Amazing stay! Amari was so wonderful and helpful!"
Braselina 2-night trip
Posted 1 hour ago
The Godfrey Hotel Boston

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
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  • 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?

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 TD Garden.

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.