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Wellesley Holiday Rentals

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Wellesley holiday rentals

Lobby lounge

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (706 reviews)
"Clean room, great staff and fantastic location for a reasonable price."
United States
April
The price is HK$1,193
HK$2,272 total
includes taxes & fees
6 Jul - 7 Jul
Global Luxury Suites Downtown Boston
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, (633 reviews)
"Excellent location and clean room with beautiful views. Very comfortable and convenient."
United States
Noelle
The price is HK$2,524
HK$2,902 total
includes taxes & fees
6 Jul - 7 Jul
Marriott Vacation Club® at Custom House, Boston
Premium bedding, desk, iron/ironing board, free WiFi

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (213 reviews)
"The rooms are very spacious and clean. I liked the lighting provided as well."
United States
Hayley
The price is HK$1,403
HK$2,964 total
includes taxes & fees
21 Jun - 22 Jun
Charlesgate Suites
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, (389 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
15 Jun - 16 Jun
Temple Place Suites
Living area

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (33 reviews)
"Charming room, fresh towels, clean!! I would stay here again."
United States
Mary
The price is HK$1,254
HK$2,432 total
includes taxes & fees
30 Jun - 1 Jul
The Chester Hotel
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, (290 reviews)
"Great location and well maintained"
United States
EDDIE
The price is HK$945
HK$1,492 total
includes taxes & fees
21 Jun - 22 Jun
Premier Suites - Bay Village
Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
8.0 out of 10, Very good, (2 reviews)
"The property was great, aside from very busy outside streets, which made it difficult to sleep, but was not the fault of the host."
United States
Nicholas
The price is HK$1,520
HK$2,513 total
includes taxes & fees
24 Jun - 25 Jun
Symple Live
Lobby

Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (288 reviews)
"Amazing location we loved it"
United States
MARLYN
The price is HK$1,591
HK$2,639 total
includes taxes & fees
15 Jun - 16 Jun
Kasa Boston at Fenway
Interior

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 HK$1,293
HK$3,232 total
includes taxes & fees
27 Jun - 28 Jun
Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
Living area

The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (37 reviews)
"Excellent location, very easy check in process, clean, just as the pictures showed online."
United States
shannon
The price is HK$4,993
HK$7,090 total
includes taxes & fees
15 Jun - 16 Jun
The Monty Boston
Interior

Furnished Apartment Near Longwood

Furnished Apartment Near Longwood
3.0 star property
North Brookline
7.4 out of 10, Good, (3 reviews)
"Easy to check in, students friendly apartment, convenient location, easy to call Uber or Lyft, and within 20 min. drive to the famous universities."
United States
Sujiang
Furnished Apartment Near Longwood
Indoor pool, pool umbrellas, pool loungers

Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (196 reviews)
"The unit smelled like cigarette smoke and was not well appointed at all. The property address given was not the one where I was to stay. Instead I had to walk to a building two blocks away which was not as nice. The neighborhood felt dicey to me."
United States
susan
The price is HK$1,942
HK$3,133 total
includes taxes & fees
6 Jul - 7 Jul
Global Luxury Suites East Boston
Terrace/patio

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,218 reviews)
"Everything was comfortable."
United States
John
The price is HK$1,262
HK$1,410 total
includes taxes & fees
5 Jul - 6 Jul
Crescent Suites Hotel
5 bedrooms, desk

Enchanting Hidden Door Escape

Enchanting Hidden Door Escape
2.0 star property
Stoneham
The price is HK$3,131
HK$6,499 total
includes taxes & fees
14 Jun - 15 Jun
Enchanting Hidden Door Escape
3 bedrooms, desk

Lakeview Getaway With Hot Tub

Lakeview Getaway With Hot Tub
2.5 star property
Billerica
The price is HK$2,688
HK$6,065 total
includes taxes & fees
15 Jun - 16 Jun
Lakeview Getaway With Hot Tub
Interior

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 HK$5,751
HK$10,252 total
includes taxes & fees
12 Jul - 13 Jul
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

Hilton Boston Back Bay

Hilton Boston Back Bay

4/10 Poor
"elevator to parking didn't work. wifi was so weak, not effective. staff gave conflicting information and manager threw new staff member under the bus. very unpleasant experience. breakfast staff was very pleasant. location good. expensive for service rendered. not up to hilton standards."
caryn 1-night trip
Posted less than an hour ago
Hilton 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?

Cozy 3BD 1BA near Beach T-10 Min from Boston: This holiday home rental outside of Wellesley is equipped with a patio, free WiFi and a Smart TV to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, 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 Copley 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.