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Our top choices for Wellesley holiday homes

Gorgeous Beacon Hills Studio next to State house

Gorgeous Beacon Hills Studio next to State house
Beacon Hill
9.6 out of 10, Exceptional, (34 reviews)
"We had a great stay and host was welcoming and responsive. Thanks!"
United States
Eric M.
The price is HK$1,639
HK$3,047 total
includes taxes & fees
20 Jul - 21 Jul
Gorgeous Beacon Hills Studio next to State house

3BR3Bth Entire House/Steps to Downtown & TD Garden

3BR3Bth Entire House/Steps to Downtown & TD Garden
North End
10.0 out of 10, Exceptional, (14 reviews)
"This place is so cool! Was incredibly clean, updated and offered all the amenities you need for a weekend get away. The location is wonderful as well with lots of markets, bakeries and restaurants all within walking distance. This is a must stay! "
United States
mary j.
The price is HK$2,541
HK$5,400 total
includes taxes & fees
28 Jul - 29 Jul
3BR3Bth Entire House/Steps to Downtown & TD Garden

Charming garden level 1 bedroom 1 bath apartment in Brockton

Charming garden level 1 bedroom 1 bath apartment in Brockton
Brockton
8.2 out of 10, Very good, (12 reviews)
"Easy to find, very comfortable, clean and convenient"
United States
David W.
The price is HK$755
HK$1,369 total
includes taxes & fees
1 Jul - 2 Jul
Charming garden level 1 bedroom 1 bath apartment in Brockton

Just Ducky: Lake Front, Easy Access to Boston, Mobility Friendly

Just Ducky: Lake Front, Easy Access to Boston, Mobility Friendly
Wilmington
The price is HK$2,497
HK$6,161 total
includes taxes & fees
30 Jun - 1 Jul
Just Ducky: Lake Front, Easy Access to Boston, Mobility Friendly

charming space in Lynn

charming space in Lynn
Lynn
The price is HK$614
HK$1,018 total
includes taxes & fees
29 Jun - 30 Jun
charming space in Lynn

Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking

Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking
South Medford
9.6 out of 10, Exceptional, (5 reviews)
"Clean rooms and comfortable beds "
United States
camilo r.
The price is HK$734
HK$2,940 total
includes taxes & fees
13 Jul - 14 Jul
Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking

✨Private Studio w/ Loft Center Historic Carlisle✨

✨Private Studio w/ Loft Center Historic Carlisle✨
Carlisle
9.4 out of 10, Exceptional, (34 reviews)
"Wonderful stay"
United States
Brent H.
The price is HK$776
HK$1,401 total
includes taxes & fees
29 Jun - 30 Jun
✨Private Studio w/ Loft Center Historic Carlisle✨

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Dorchester
8.8 out of 10, Excellent, (5 reviews)
"Great place for our overnight stay. Red line was close by to get us in and out of Boston. Host was incredibly responsive. She suggested a restaurant close by, via Cannuccia.. stunning pastries on the weekend. "
United States
Ingrid
The price is HK$993
HK$1,601 total
includes taxes & fees
16 Jul - 17 Jul
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

2 bedroom's 1 bathroom 10 min-Airport/Downtown Boston 7 min-Encore Casino

2 bedroom's 1 bathroom 10 min-Airport/Downtown Boston 7 min-Encore Casino
Everett
10.0 out of 10, Exceptional, (8 reviews)
"Great neighborhood! House is beautiful and alot bigger then expected! If we ever get back to the area, this would be my first pick to stay. "
United States
Danielle s.
The price is HK$1,270
HK$2,829 total
includes taxes & fees
29 Jun - 30 Jun
2 bedroom's 1 bathroom 10 min-Airport/Downtown Boston 7 min-Encore Casino

Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
Westwood
10.0 out of 10, Exceptional, (1 review)
"Easy-to-find location and charming accommodations. Everything was organized well and very clean. Would highly recommend this listing."
United States
Eva O.
The price is HK$988
HK$1,550 total
includes taxes & fees
4 Jul - 5 Jul
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

Charming 3-bedroom house in delightful Ashland for your getaway

Charming 3-bedroom house in delightful Ashland for your getaway
Ashland
10.0 out of 10, Exceptional, (2 reviews)
"This is our second stay here and both times have been good. The house is quiet, even for it being on a well traveled road. "
United States
John W.
The price is HK$1,101
HK$2,341 total
includes taxes & fees
5 Jul - 6 Jul
Charming 3-bedroom house in delightful Ashland for your getaway

Eagles Landing - Logan Airport

Eagles Landing - Logan Airport
East Boston
The price is HK$865
HK$1,692 total
includes taxes & fees
30 Jun - 1 Jul
Eagles Landing - Logan Airport

Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams

Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams
Quincy
9.4 out of 10, Exceptional, (3 reviews)
"It was close to the location where we were attending an event."
United States
Erica M.
The price is HK$1,294
HK$2,242 total
includes taxes & fees
6 Jul - 7 Jul
Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams

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
9.8 out of 10, Exceptional, (25 reviews)
"Clean home, comfortable beds, host very responsive."
United States
Richard M.
The price is HK$2,026
HK$3,051 total
includes taxes & fees
5 Jul - 6 Jul
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

Spacious & Convenient 1BR unit-20min to Boston

Spacious & Convenient 1BR unit-20min to Boston
Melrose
9.8 out of 10, Exceptional, (16 reviews)
"very pleased with our stay! "
United States
Patrick G.
The price is HK$1,561
HK$3,206 total
includes taxes & fees
14 Jul - 15 Jul
Spacious & Convenient 1BR unit-20min to Boston

totally remodeled house with fitness room, close to Boston and Worcester

totally remodeled house with fitness room, close to Boston and Worcester
Framingham
9.2 out of 10, Wonderful, (11 reviews)
"Property was as described. It was clean and owner was very responsive. Could walk to great coffee shop. "
United States
michelle s.
The price is HK$812
HK$1,818 total
includes taxes & fees
29 Jun - 30 Jun
totally remodeled house with fitness room, close to Boston and Worcester

Lorenzo Inn

Lorenzo Inn
Dorchester
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful house. Very well furnished and equipped. Friendly host. Comfortable beds. Easy to quickly get town centre in an Uber. Highly recommend."
United Kingdom
patrick
The price is HK$2,039
HK$3,020 total
includes taxes & fees
19 Jul - 20 Jul
Lorenzo Inn

Newly Renovated 2 Bedroom in Southie!

Newly Renovated 2 Bedroom in Southie!
South Boston
The price is HK$1,412
HK$2,524 total
includes taxes & fees
30 Jun - 1 Jul
Newly Renovated 2 Bedroom in Southie!

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

Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
Bayside
9.8 out of 10, Exceptional, (17 reviews)
"Great property, clean, close to a baseball field which we loved. Super close to a beautiful beach that our kids enjoyed skim boarding and swimming in. "
United States
Candice C.
The price is HK$1,976
HK$4,029 total
includes taxes & fees
1 Jul - 2 Jul
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383
Quincy
9.8 out of 10, Exceptional, (52 reviews)
"The host was welcoming and answered all of my messages to her really fast. The house itself was beautiful, very clean, and close to everything."
United States
Deletra S.
The price is HK$1,419
HK$2,996 total
includes taxes & fees
30 Jun - 1 Jul
Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383
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

Find out more about Wellesley

Wellesley Vacation Homes information

Number of reviews
Accommodation
543 Vacation Homes
Lowest Price
HK$6,054
Highest Price
HK$7,360

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