Holiday Homes in Winthrop

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Winthrop

NEW 2BR Historic Marblehead Home+Minutes to Beach
Smart TV, fireplace

NEW 2BR Historic Marblehead Home+Minutes to Beach

2.0 star property
10.0 out of 10, Exceptional, (12)
"We loved staying here, enjoying all that Marblehead had to offer. It was the perfect distance from both Salem and Boston and had lots to offer when we decided to stay in. We came on an unseasonably cold week but stayed nice and cozy in the Vrbo. Highly recommend! "
The price is AU$624
includes taxes & fees
2 Sept - 3 Sept
NEW 2BR Historic Marblehead Home+Minutes to Beach
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 AU$207
includes taxes & fees
28 Aug - 29 Aug
Casa Castor • Private Room 1
Moody Salem Home Away From Home
Fridge, microwave, oven, stovetop

Moody Salem Home Away From Home

10.0 out of 10, Exceptional, (14)
"Cozy little corner , perfect for taking a break and relaxing for a bit. Well situated and close to everything the city has to offer. Loved my stay here"
The price is AU$439
includes taxes & fees
26 Aug - 27 Aug
Moody Salem Home Away From Home
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 AU$578
includes taxes & fees
26 Aug - 27 Aug
Spacious & Convenient 1BR unit-20min to Boston
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 AU$620
includes taxes & fees
1 Sept - 2 Sept
Beacon Hill Studio with Full Kitchen, Short Walk to MGH, Multiple Train Lines
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 AU$508
includes taxes & fees
1 Sept - 2 Sept
PEACE IN THE CITY - Humble Luxury minutes from Boston, Beach & Casino
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 AU$833
includes taxes & fees
14 Sept - 15 Sept
CityScape: Urban Convenience Meets Affordability in this Modern City Living in the Heart of Chelsea!
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!!"
The price is AU$789
includes taxes & fees
24 Aug - 25 Aug
Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.
Entire Lower Level of the House, Across From The Beach
Beach

Entire Lower Level of the House, Across From The Beach

9.8 out of 10, Exceptional, (17)
"Loved getting to visit the beach and the short drive to Salem!"
The price is AU$578
includes taxes & fees
7 Sept - 8 Sept
Entire Lower Level of the House, Across From The Beach
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 AU$447
includes taxes & fees
25 Aug - 26 Aug
Opulence Living close to Boston- Family and pet friendly
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 AU$511
includes taxes & fees
26 Aug - 27 Aug
Grandeur Living near Boston - 3bed 1 bath
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 AU$422
includes taxes & fees
24 Aug - 25 Aug
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)
"They where beautiful people from the start and great vibes "
The price is AU$353
includes taxes & fees
1 Sept - 2 Sept
Charming 2-bedroom apartment with WiFi, AC in superb Canton
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 AU$565
includes taxes & fees
24 Aug - 25 Aug
558/2 - 3BR Boston - Modern Nest near Franklin Park
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 AU$620
includes taxes & fees
31 Aug - 1 Sept
Hidden Gem right in the city of Boston!
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 AU$643
includes taxes & fees
1 Sept - 2 Sept
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
3BR3Bth Entire House/Steps to Downtown & TD Garden
Interior

3BR3Bth Entire House/Steps to Downtown & TD Garden

The price is AU$1,223
includes taxes & fees
24 Aug - 25 Aug
3BR3Bth Entire House/Steps to Downtown & TD Garden
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 AU$766
includes taxes & fees
24 Aug - 25 Aug
Cozy three-bedroom home close to Boston
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Fridge, microwave, oven, stovetop

Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

9.6 out of 10, Exceptional, (85)
"This place is so well located. So close everything. EXCELLENT.If one complaint sometimes upstairs people are very loud. Overall great stay"
The price is AU$631
includes taxes & fees
21 Sept - 22 Sept
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
37-SPRING GETAWAY EARLY BIRD 10%! Greater Boston Cozy Townhouse
Exterior

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

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 AU$549
includes taxes & fees
24 Aug - 25 Aug
37-SPRING GETAWAY EARLY BIRD 10%! Greater Boston Cozy Townhouse
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 Winthrop Hotel Reviews

The Langham, Boston

The Langham, Boston

10/10 Excellent
"Great place"
Mariana 3-night trip
Posted 21 hours ago
The Langham, Boston