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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Wellesley vacation homes

Interior
3BR3Bth Entire House/Steps to Downtown & TD Garden

3BR3Bth Entire House/Steps to Downtown & TD Garden

North End
10.0 out of 10, Exceptional, (2)
"Clean and bright throughout, host was great with timely responses to all inquiries. Maybe not the best for young children bc of the all the stairs (which are beautiful btw)."
United States
Margaret S.
The price is AED 920
AED 2,147 total
includes taxes & fees
15 Dec - 16 Dec
3BR3Bth Entire House/Steps to Downtown & TD Garden
Exterior
37 - 3BR Quincy - Cozy Townhouse near Adams Park

37 - 3BR Quincy - Cozy Townhouse near Adams Park

Quincy
9.2 out of 10, Wonderful, (36)
"property was as described, very clean and remodeled. Owner was a pleasure to deal with. Would stay again in the future. "
United States
Andrew A.
The price is AED 356
AED 1,152 total
includes taxes & fees
11 Dec - 12 Dec
37 - 3BR Quincy - Cozy Townhouse near Adams Park
Terrace/patio
Gorgeous Beacon Hills Studio next to State house

Gorgeous Beacon Hills Studio next to State house

Beacon Hill
9.8 out of 10, Exceptional, (30)
"As promised in listing, great location and property management team we will be back!"
United States
Cathie B.
The price is AED 731
AED 1,376 total
includes taxes & fees
8 Jan - 9 January 2026
Gorgeous Beacon Hills Studio next to State house
Property grounds
383 - 3BR - Quincy Chic House near Adams Park

383 - 3BR - Quincy Chic House near Adams Park

Quincy
9.6 out of 10, Exceptional, (44)
"Beautiful home! Neighborhood is a little older, but the property is beautiful and close to Boston!"
United States
Christopher S.
The price is AED 418
AED 1,234 total
includes taxes & fees
11 Dec - 12 Dec
383 - 3BR - Quincy Chic House near Adams Park
Sun loungers, beach towels
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, (15)
"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 AED 625
AED 1,475 total
includes taxes & fees
16 Dec - 17 Dec
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
Fridge, microwave, oven, stovetop
41 - 3BR Quincy - Lovely Townhouse near Adams

41 - 3BR Quincy - Lovely Townhouse near Adams

Quincy
9.4 out of 10, Exceptional, (26)
"Nice and clean place with parking. All questions were answered quickly. We enjoyed our stay!"
United States
victoria
The price is AED 372
AED 1,174 total
includes taxes & fees
11 Dec - 12 Dec
41 - 3BR Quincy - Lovely Townhouse near Adams
Fridge, microwave, oven, stovetop
LUXE 3BR Near Boston, Airport, and Beach!

LUXE 3BR Near Boston, Airport, and Beach!

Revere
9.8 out of 10, Exceptional, (6)
"Very nice and comfortable place to stay in a very quiet neighborhood. Host was very caring and quick to respond. Two thumbs up👍👍"
Canada
Irma S.
The price is AED 342
AED 1,125 total
includes taxes & fees
14 Dec - 15 Dec
LUXE 3BR Near Boston, Airport, and Beach!
Interior
Hidden Gem right in the city of Boston!

Hidden Gem right in the city of Boston!

Hyde Park
9.6 out of 10, Exceptional, (24)
"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."
United States
TIARA V.
The price is AED 476
AED 1,425 total
includes taxes & fees
16 Dec - 17 Dec
Hidden Gem right in the city of Boston!
Interior
Charming garden level 1 bedroom 1 bath apartment in Brockton

Charming garden level 1 bedroom 1 bath apartment in Brockton

Brockton
7.6 out of 10, Good, (8)
"Easy to find, very comfortable, clean and convenient"
United States
David W.
The price is AED 349
AED 636 total
includes taxes & fees
4 Jan - 5 January 2026
Charming garden level 1 bedroom 1 bath apartment in Brockton
Private kitchen
Cozy 4BD/2BA Near Boston-Encore-T-Station & Diners

Cozy 4BD/2BA Near Boston-Encore-T-Station & Diners

East Somerville
Cozy 4BD/2BA Near Boston-Encore-T-Station & Diners
Beach
Beautiful Hill top 2BR Near Boston & Salem

Beautiful Hill top 2BR Near Boston & Salem

2.0 star property
Lynn
Beautiful Hill top 2BR Near Boston & Salem
Beach
Spectacular Ocean Sunsets I Pet Friendly

Spectacular Ocean Sunsets I Pet Friendly

Weymouth
9.4 out of 10, Exceptional, (3)
"We had a wonderful stay in this beautiful spot!"
United States
Laura A.
The price is AED 694
AED 1,600 total
includes taxes & fees
11 Dec - 12 Dec
Spectacular Ocean Sunsets I Pet Friendly
4 bedrooms, desk, iron/ironing board, travel crib
Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area

Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area

Dorchester
9.6 out of 10, Exceptional, (14)
"Amazing location close to everything you are going to want to see in Boston, and great communication with the host."
United States
Shane M.
The price is AED 593
AED 1,484 total
includes taxes & fees
15 Dec - 16 Dec
Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area
Fridge, microwave, oven, stovetop
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, (5)
"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 AED 595
AED 1,305 total
includes taxes & fees
30 Dec - 31 Dec
2 bedroom's 1 bathroom 10 min-Airport/Downtown Boston 7 min-Encore Casino
Exterior
Cozy Large House close to TUFTS/Harvard/MIT 4BR

Cozy Large House close to TUFTS/Harvard/MIT 4BR

South Medford
9.6 out of 10, Exceptional, (8)
"Very nice house check in was easy there was parking and the beds were comfortable. Shower with great water pressure and a well stocked kitchen for making and eating food! "
United States
Ronan B.
The price is AED 804
AED 2,055 total
includes taxes & fees
11 Dec - 12 Dec
Cozy Large House close to TUFTS/Harvard/MIT 4BR
Cookware/dishes/utensils
Cozy 3 bedroom - Free Parking, close to buses.

Cozy 3 bedroom - Free Parking, close to buses.

Dorchester
10.0 out of 10, Exceptional, (1)
"The space was great! Exactly what we needed as coworkers travelling for a conference. Host was very communicative, the place was clean and safe, and the beds were very comfortable. Would recommend to anyone!"
Canada
Melissa S.
The price is AED 628
AED 1,672 total
includes taxes & fees
30 Dec - 31 Dec
Cozy 3 bedroom - Free Parking, close to buses.
Fridge, microwave, oven, stovetop
Centrally located in the heart of Boston near T

Centrally located in the heart of Boston near T

Dorchester
9.0 out of 10, Wonderful, (20)
"This was the best vacation, the owner was available to talk anytime to make my stay pleasant."
United States
ADEWALE A.
The price is AED 826
AED 1,870 total
includes taxes & fees
11 Dec - 12 Dec
Centrally located in the heart of Boston near T
Stereo
PEACE IN THE CITY - Humble Luxury minutes from Boston, Beach & Casino

PEACE IN THE CITY - Humble Luxury minutes from Boston, Beach & Casino

Everett
10.0 out of 10, Exceptional, (2)
"We went to a concert at TD Gardens and this place was perfect for 2 couples in close proximity!"
United States
Chelsea J.
The price is AED 650
AED 1,214 total
includes taxes & fees
15 Dec - 16 Dec
PEACE IN THE CITY - Humble Luxury minutes from Boston, Beach & Casino
Exterior
✨Private Studio w/ Loft Center Historic Carlisle✨

✨Private Studio w/ Loft Center Historic Carlisle✨

Carlisle
9.4 out of 10, Exceptional, (33)
"We had a great stay! The place was perfect for our weekend trip. We were able to hit all of the spots we planned, with the central location!"
United States
C Z.
The price is AED 459
AED 757 total
includes taxes & fees
8 Jan - 9 January 2026
✨Private Studio w/ Loft Center Historic Carlisle✨
Fridge, microwave, oven, stovetop
Stylish Boston-Area Duplex - Free Parking, Yard, Comfortable Stay

Stylish Boston-Area Duplex - Free Parking, Yard, Comfortable Stay

Everett
9.4 out of 10, Exceptional, (28)
"It worked perfect for me and my friends and was a nice distance from the city. Amenities were nice and the whole process was super easy!"
United States
Brendan D.
The price is AED 617
AED 1,526 total
includes taxes & fees
11 Dec - 12 Dec
Stylish Boston-Area Duplex - Free Parking, Yard, Comfortable Stay
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

Wyndham Boston Beacon Hill

Wyndham Boston Beacon Hill

10/10 Excellent
"Staff is very friendly and accommodating. Room was clean and the bed was comfortable. Breakfast was very good."
Geraldine 1-night trip
Posted 2 days ago
Wyndham Boston Beacon Hill