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Top Holiday Rentals in Wellesley

Charming garden level 1 bedroom 1 bath apartment in Brockton

9.0 out of 10, Wonderful, (2)
"The property is clean and functional. It’s a basement apartment without AC so keep that in mind for warmer months. Busy neighborhood so backing out of the driveway on weekday mornings is tricky. "
The price is £138
includes taxes & fees
23 Jul - 24 Jul
Charming garden level 1 bedroom 1 bath apartment in Brockton

Casa Castor • Private Room 1

The price is £95
includes taxes & fees
23 Jul - 24 Jul
Casa Castor • Private Room 1

CityScape: Urban Convenience Meets Affordability in this Modern City Living in the Heart of Chelsea!

2.0 star property
9.4 out of 10, Exceptional, (23)
"We stayed for a short trip for a concert, and it worked out great! The space was very comfortable and clean, and was very conveniently located! Would stay again!"
The price is £392
includes taxes & fees
27 Jul - 28 Jul
CityScape: Urban Convenience Meets Affordability in this Modern City Living in the Heart of Chelsea!

Spacious & Convenient 1BR unit-20min to Boston

2.0 star property
9.8 out of 10, Exceptional, (10)
"Property was small and cozy. Quiet neighborhood and had all amenities except for coffee creamer. "
The price is £283
includes taxes & fees
31 Jul - 1 Aug
Spacious & Convenient 1BR unit-20min to Boston

Gorgeous Beacon Hills Studio next to State house

10.0 out of 10, Exceptional, (23)
"Great location, easy access to TD Garden and restaurants. Very clean, and comfy bed. We would definitely recommend. Thanks for a great week!"
The price is £307
includes taxes & fees
13 Aug - 14 Aug
Gorgeous Beacon Hills Studio next to State house

Grandeur Living near Boston - 3bed 1 bath

8.8 out of 10, Excellent, (8)
"Lovely, comfortable apartment, lovely, gracious hosts."
The price is £219
includes taxes & fees
28 Jul - 29 Jul
Grandeur Living near Boston - 3bed 1 bath

Opulence Living close to Boston- Family and pet friendly

8.8 out of 10, Excellent, (5)
"Just a group of friends getting ready for a weekend wedding- we couldn’t have asked for a better place - we all felt like we were at home. The communication was great. The pictures do this place no justice - the rooms are giant and there is PLENTY of space for your group"
The price is £218
includes taxes & fees
28 Jul - 29 Jul
Opulence Living close to Boston- Family and pet friendly

LUXE 3BR Near Boston, Airport, and Beach!

10.0 out of 10, Exceptional, (4)
"Very nice and comfortable place to stay in a very quiet neighborhood. Host was very caring and quick to respond. Two thumbs up👍👍"
The price is £337
includes taxes & fees
23 Jul - 24 Jul
LUXE 3BR Near Boston, Airport, and Beach!

Hidden Gem right in the city of Boston!

9.8 out of 10, Exceptional, (21)
"We were in town for a conference for work and didn't want to stay in a hotel. The place was very clean and smelled amazing. Perfect space 3 friends to stay. Host was great she answered when reaching out before the stay and the arrival was seamless."
The price is £313
includes taxes & fees
19 Aug - 20 Aug
Hidden Gem right in the city of Boston!

Cozy three-bedroom home close to Boston

10.0 out of 10, Exceptional, (35)
"We were very happy in this clean, comfortable, and welcoming home with all amenities included for a relaxing vacation with friends. Nearby restaurants and train station allowed for easy access to the city and meals."
The price is £399
includes taxes & fees
21 Aug - 22 Aug
Cozy three-bedroom home close to Boston

✨Private Studio w/ Loft Center Historic Carlisle✨

9.4 out of 10, Exceptional, (19)
"Charming and impeccably clean place to stay for a quick trip out to the Greater Boston Area for travel and exploration. Easy access to main roads and visiting Kimball Farm for some great ice cream right down the road is an absolute must! "
The price is £157
includes taxes & fees
25 Jul - 26 Jul
✨Private Studio w/ Loft Center Historic Carlisle✨

85b Spacious 3-bedroom apartment in delightful Boston

10.0 out of 10, Exceptional, (1)
"This place was fabulous! Very clean and cute. Check-in/out was very easy. The host responded to messages within minutes and was very kind. Would definitely stay again. "
The price is £333
includes taxes & fees
23 Jul - 24 Jul
85b Spacious 3-bedroom apartment in delightful Boston

37-SPRING GETAWAY EARLY BIRD 10%! Greater Boston Cozy Townhouse

9.0 out of 10, Wonderful, (30)
"This was a great stay in a great location. Unit was clean and the mananger was courteous and very responsive"
The price is £265
includes taxes & fees
23 Jul - 24 Jul
37-SPRING GETAWAY EARLY BIRD 10%! Greater Boston Cozy Townhouse

558/1 - 3BR Boston - Modern Nest near Franklin Park

8.6 out of 10, Excellent, (4)
"The apartment looks recently renovated, is clean and spacious,the mattresses were really good"
The price is £346
includes taxes & fees
30 Jul - 31 Jul
558/1 - 3BR Boston - Modern Nest near Franklin Park

Charming 2-bedroom apartment with WiFi, AC in superb Canton

9.8 out of 10, Exceptional, (8)
"Beautiful home and quiet place. Exactly what we were looking for. Little trouble with lock codes but overall a wonderful stay."
The price is £174
includes taxes & fees
31 Jul - 1 Aug
Charming 2-bedroom apartment with WiFi, AC in superb Canton

Cozy House close to TUFTS, Harvard, MIT 3BR

10.0 out of 10, Exceptional, (13)
"Great stay and as advertised. Beds were very comfortable, unit was very clean, and ideal location for visiting Medford area!"
The price is £718
includes taxes & fees
28 Jul - 29 Jul
Cozy House close to TUFTS, Harvard, MIT 3BR

Under the Sun Apartment

10.0 out of 10, Exceptional, (1)
"We stayed durinig Marathon weekend to run the marathon on Monday. The unit was perfect for our size and very comfortable. The living spaces were surprisingly larger than expected, very comfortable with lots of space to spread out and relax. The place was freshly updated and very well done. The neighborhood was quiet and relaxing and we were able experience Boston living. We would definitely look to stay again if find ourselves back in Boston. "
The price is £427
includes taxes & fees
28 Jul - 29 Jul
Under the Sun Apartment

Casa Castor • Private Room 3

The price is £95
includes taxes & fees
23 Jul - 24 Jul
Casa Castor • Private Room 3

558/3 - 3BR Boston - Modern Nest near Franklin Park

10.0 out of 10, Exceptional, (1)
"Excellent host and property. Would recommend to friends and family! "
The price is £318
includes taxes & fees
28 Jul - 29 Jul
558/3 - 3BR Boston - Modern Nest near Franklin Park

Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

10.0 out of 10, Exceptional, (12)
"The rental was lovely in a quiet area of town. Our host was wonderful and aways responded quickly with and questions we had. "
The price is £473
includes taxes & fees
15 Aug - 16 Aug
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
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

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?

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi: This holiday home rental outside of Wellesley is located in the city centre, and offers a balcony, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 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 11 Expedia holiday rentals in Wellesley for a memorable holiday.

What can I see and do in Wellesley?

Charles River and Elm Bank Reservation 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.