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Wellesley Vacation Rentals

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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select Wellesley Vacation Homes

Our top choices for Wellesley vacation homes

Casa Castor • Private Room 1
Free WiFi, bed sheets

Casa Castor • Private Room 1

10.0 out of 10, Exceptional, (1)
"We loved staying at Judith's place! Much recommended!"
The price is CA $137
CA $183 total
includes taxes & fees
Aug 26 - Aug 27
Casa Castor • Private Room 1
Spacious & Convenient 1BR unit-20min to Boston
Exterior

Spacious & Convenient 1BR unit-20min to Boston

2.0 star property
9.8 out of 10, Exceptional, (10)
"The host stays in the same building and are friendly and helpful. We enjoy the timely response from th host, the clean and modern property, and the convenient location! "
The price is CA $231
CA $513 total
includes taxes & fees
Aug 26 - Aug 27
Spacious & Convenient 1BR unit-20min to Boston
CityScape: Urban Convenience Meets Affordability in this Modern City Living in the Heart of Chelsea!
Fishing

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, (27)
"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 CA $274
CA $740 total
includes taxes & fees
Sep 14 - Sep 15
CityScape: Urban Convenience Meets Affordability in this Modern City Living in the Heart of Chelsea!
Opulence Living close to Boston- Family and pet friendly
Fridge, microwave, oven, stovetop

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 CA $207
CA $395 total
includes taxes & fees
Aug 26 - Aug 27
Opulence Living close to Boston- Family and pet friendly
Charming garden level 1 bedroom 1 bath apartment in Brockton
Interior

Charming garden level 1 bedroom 1 bath apartment in Brockton

8.6 out of 10, Excellent, (4)
"Easy to find, very comfortable, clean and convenient"
The price is CA $124
CA $232 total
includes taxes & fees
Sep 3 - Sep 4
Charming garden level 1 bedroom 1 bath apartment in Brockton
Beacon Hill Studio with Full Kitchen, Short Walk to MGH, Multiple Train Lines
Smart TV

Beacon Hill Studio with Full Kitchen, Short Walk to MGH, Multiple Train Lines

The price is CA $243
CA $556 total
includes taxes & fees
Aug 27 - Aug 28
Beacon Hill Studio with Full Kitchen, Short Walk to MGH, Multiple Train Lines
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
Sun loungers, beach towels

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

10.0 out of 10, Exceptional, (12)
"Easy to find, close to everything, very clean"
The price is CA $248
CA $570 total
includes taxes & fees
Sep 1 - Sep 2
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.
3 bedrooms, desk, iron/ironing board, WiFi

Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.

2.0 star property
9.8 out of 10, Exceptional, (8)
"Lived the location and light!!Thanks!!"
Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.
PEACE IN THE CITY - Humble Luxury minutes from Boston, Beach & Casino
Stereo

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

10.0 out of 10, Exceptional, (2)
"Great overall experience. Apartment has anything one needs, clean and functional. Home owner expremely good communicator. Will happily come back. "
The price is CA $310
CA $539 total
includes taxes & fees
Aug 27 - Aug 28
PEACE IN THE CITY - Humble Luxury minutes from Boston, Beach & Casino
558/2 - 3BR Boston - Modern Nest near Franklin Park
Interior

558/2 - 3BR Boston - Modern Nest near Franklin Park

10.0 out of 10, Exceptional, (3)
"Great place with very usable space. Quiet yet very convenient --- walking distance to CVS and several restaurants, a grocery store, and more. "
The price is CA $175
CA $500 total
includes taxes & fees
Aug 26 - Aug 27
558/2 - 3BR Boston - Modern Nest near Franklin Park
✨Private Studio w/ Loft Center Historic Carlisle✨
Exterior

✨Private Studio w/ Loft Center Historic Carlisle✨

9.4 out of 10, Exceptional, (25)
"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 CA $123
CA $218 total
includes taxes & fees
Aug 26 - Aug 27
✨Private Studio w/ Loft Center Historic Carlisle✨
Grandeur Living near Boston - 3bed 1 bath
Interior

Grandeur Living near Boston - 3bed 1 bath

8.8 out of 10, Excellent, (8)
"This place was very cozy, super cute and very clean. Owners were very attentive and responded within minutes of messages. We would def stay at this place again!! "
The price is CA $250
CA $449 total
includes taxes & fees
Aug 26 - Aug 27
Grandeur Living near Boston - 3bed 1 bath
2 bedroom's 1 bathroom 10 min-Airport/Downtown Boston 7 min-Encore Casino
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (3)
"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. "
The price is CA $231
CA $507 total
includes taxes & fees
Sep 11 - Sep 12
2 bedroom's 1 bathroom 10 min-Airport/Downtown Boston 7 min-Encore Casino
Cozy three-bedroom home close to Boston
Property grounds

Cozy three-bedroom home close to Boston

10.0 out of 10, Exceptional, (37)
"Confortable Beds, easy to find, close to the T to get in and out of town easily. Friendly hosts. Highly recommend "
The price is CA $311
CA $673 total
includes taxes & fees
Sep 1 - Sep 2
Cozy three-bedroom home close to Boston
Hidden Gem right in the city of Boston!
Interior

Hidden Gem right in the city of Boston!

9.6 out of 10, Exceptional, (22)
"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 CA $179
CA $543 total
includes taxes & fees
Aug 31 - Sep 1
Hidden Gem right in the city of Boston!
PEACEFUL CHARM - Humble Luxury minutes from Boston, Beach & Casino
Fridge, dishwasher, cookware/dishes/utensils

PEACEFUL CHARM - Humble Luxury minutes from Boston, Beach & Casino

9.0 out of 10, Wonderful, (4)
"Barry was just the best. Great communication. Lovely home. Described just as listed maybe even nicer. We enjoyed our stay. Pretty close to everything. Thank you for sharing your home with us! "
The price is CA $199
CA $402 total
includes taxes & fees
Aug 27 - Aug 28
PEACEFUL CHARM - Humble Luxury minutes from Boston, Beach & Casino
Charming 2-bedroom apartment with WiFi, AC in superb Canton
Exterior

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

9.8 out of 10, Exceptional, (10)
"The place looked very clean and definitely made for a comfy stay. Instructions and service from the host were clear and timely."
The price is CA $247
CA $315 total
includes taxes & fees
Aug 26 - Aug 27
Charming 2-bedroom apartment with WiFi, AC in superb Canton
37 - 3BR Quincy - Cozy Townhouse near Adams Park
Exterior

37 - 3BR Quincy - Cozy Townhouse near Adams Park

9.0 out of 10, Wonderful, (31)
"This was a great stay in a great location. Unit was clean and the mananger was courteous and very responsive"
The price is CA $175
CA $486 total
includes taxes & fees
Aug 26 - Aug 27
37 - 3BR Quincy - Cozy Townhouse near Adams Park
41 - 3BR Quincy - Lovely Townhouse near Adams
Fridge, microwave, oven, stovetop

41 - 3BR Quincy - Lovely Townhouse near Adams

9.4 out of 10, Exceptional, (23)
"Nice and clean place with parking. All questions were answered quickly. We enjoyed our stay!"
The price is CA $185
CA $499 total
includes taxes & fees
Aug 26 - Aug 27
41 - 3BR Quincy - Lovely Townhouse near Adams
85a Charming, Cozy 3BR, 2BA Home Near Downtown Boston
Terrace/patio

85a Charming, Cozy 3BR, 2BA Home Near Downtown Boston

10.0 out of 10, Exceptional, (3)
"Everything was clean and pleasant "
The price is CA $109
CA $434 total
includes taxes & fees
Sep 22 - Sep 23
85a Charming, Cozy 3BR, 2BA Home Near Downtown Boston
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

Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor

10/10 Excellent
"Very nice property "
BRUCE 1-night trip
Posted 5 hours ago
Hyatt Regency Boston Harbor