A coastal town with a lighthouse, sandy beach, and residential buildings.

Winthrop Vacation Rentals

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Our top choices for Winthrop vacation homes

1. Steps from the ocean - minutes from Boston

Steps from the ocean - minutes from Boston
Winthrop
9.8 out of 10, Exceptional, (6 reviews)
The price is CA $266
CA $546 total
includes taxes & fees
Nov 18 - Nov 19
Steps from the ocean - minutes from Boston

2. Modern 2BR Getaway Near Revere Beach

Modern 2BR Getaway Near Revere Beach
Revere
10.0 out of 10, Exceptional, (1 review)
"Great home! Quiet neighborhood, great home, and excellent communication from the host. We had a great stay."
United States
Steve S.
The price is CA $312
CA $524 total
includes taxes & fees
Nov 15 - Nov 16
Modern 2BR Getaway Near Revere Beach

3. Stylish 3BR Revere Home|Sleeps 8|Near Boston&Beach

Stylish 3BR Revere Home|Sleeps 8|Near Boston&Beach
Revere
10.0 out of 10, Exceptional, (6 reviews)
"The apartment is well set up for a group and served us really well!"
United States
Sarah T.
The price is CA $383
CA $605 total
includes taxes & fees
Nov 16 - Nov 17
Stylish 3BR Revere Home|Sleeps 8|Near Boston&Beach

4. 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, (3 reviews)
"Beautiful and clean. Very friendly and helpful host. If ever in the area would definitely choose this lovely home first!"
United States
Dawn B.
The price is CA $227
CA $419 total
includes taxes & fees
Nov 13 - Nov 14
PEACE IN THE CITY - Humble Luxury minutes from Boston, Beach & Casino

5. Luxury 3BR • Free Parking • 10 Min to Logan

Luxury 3BR • Free Parking • 10 Min to Logan
Revere
10.0 out of 10, Exceptional, (1 review)
"Great property. New and clean"
United States
Nash B.
The price is CA $277
CA $633 total
includes taxes & fees
Nov 15 - Nov 16
Luxury 3BR • Free Parking • 10 Min to Logan

6. 3BR Home ♥ Pet-Friendly | Free Parking

3BR Home ♥ Pet-Friendly | Free Parking
Revere Beach
9.0 out of 10, Wonderful, (8 reviews)
"Very nice place, suited our needs perfectly - very clean, quite neighborhood. Definitely will recommend."
United States
Minerva P.
The price is CA $511
CA $908 total
includes taxes & fees
Nov 17 - Nov 18
3BR Home ♥ Pet-Friendly | Free Parking

7. Home for Families | Sleeps 11 | 5 min Downtown

Home for Families | Sleeps 11 | 5 min Downtown
Chelsea
10.0 out of 10, Exceptional, (1 review)
The price is CA $467
CA $510 total
includes taxes & fees
Dec 13 - Dec 14
Home for Families | Sleeps 11 | 5 min Downtown

8. Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Chelsea
9.4 out of 10, Exceptional, (129 reviews)
"Great stay for a couple of nights. Great location."
United States
Kevin C.
The price is CA $534
CA $972 total
includes taxes & fees
Nov 16 - Nov 17
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

9. Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking

Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking
Ward Two
9.8 out of 10, Exceptional, (20 reviews)
"Easy access to the trains and buses, great food within a few blocks"
United States
Mike w.
The price is CA $180
CA $434 total
includes taxes & fees
Nov 16 - Nov 17
Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking

10. 3BR3Bth Entire House/Steps to Downtown & TD Garden

3BR3Bth Entire House/Steps to Downtown & TD Garden
North End
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful property, very clean and modern with the perfect location."
United States
Joel F.
The price is CA $300
CA $729 total
includes taxes & fees
Dec 8 - Dec 9
3BR3Bth Entire House/Steps to Downtown & TD Garden

11. Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem

Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem
Everett
8.8 out of 10, Excellent, (50 reviews)
"This is our second time staying here. We find it so nice and great for traveling to Boston! The host is great and responsive."
United States
Shannon K.
The price is CA $249
CA $587 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem

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

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Dorchester
9.6 out of 10, Exceptional, (11 reviews)
"Amazing place and great host!"
United States
Harmoni C.
The price is CA $192
CA $292 total
includes taxes & fees
Nov 16 - Nov 17
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

13. Newly Renovated 2 Bedroom in Southie!

Newly Renovated 2 Bedroom in Southie!
South Boston
The price is CA $230
CA $460 total
includes taxes & fees
Nov 15 - Nov 16
Newly Renovated 2 Bedroom in Southie!

14. The Everett House - Five Bedroom House, Sleeps 11

The Everett House - Five Bedroom House, Sleeps 11
Everett
10.0 out of 10, Exceptional, (3 reviews)
"We stayed here for my brother’s MIT graduation, and I cannot say enough good things about this stunning property. Finding a home that comfortably fits the whole family can be a challenge, but this place was absolutely perfect. The house is gorgeous, incredibly spacious, and felt like a true home away from home. Being so close to Cambridge made our commute to the commencement events stress-free. If you’re looking for a beautiful, high-end spot for a family gathering, look no further. Five stars...
United States
Meshullam
The price is CA $693
CA $1,030 total
includes taxes & fees
Nov 30 - Dec 1
The Everett House - Five Bedroom House, Sleeps 11

15. LUXE 4BDR/2BA Near Boston- T-Station & Encore Casino

LUXE 4BDR/2BA Near Boston- T-Station & Encore Casino
East Somerville
9.6 out of 10, Exceptional, (8 reviews)
"Very sweet place to stay. Located in a very nice area. Close to the "T" and very walkable "
United States
Tobakeion B.
The price is CA $200
CA $588 total
includes taxes & fees
Nov 17 - Nov 18
LUXE 4BDR/2BA Near Boston- T-Station & Encore Casino

16. 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
8.6 out of 10, Excellent, (19 reviews)
"Great place, friendly check-in"
United States
Anonymous traveller
The price is CA $230
CA $625 total
includes taxes & fees
Nov 28 - Nov 29
Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking

17. 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, (24 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 CA $241
CA $547 total
includes taxes & fees
Nov 16 - Nov 17
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

18. Spacious & Convenient 1BR unit-20min to Boston

Spacious & Convenient 1BR unit-20min to Boston
Melrose
9.6 out of 10, Exceptional, (20 reviews)
"very pleased with our stay! "
United States
Patrick G.
The price is CA $254
CA $523 total
includes taxes & fees
Nov 16 - Nov 17
Spacious & Convenient 1BR unit-20min to Boston

19. Gorgeous Beacon Hills Studio next to State house

Gorgeous Beacon Hills Studio next to State house
Beacon Hill
9.6 out of 10, Exceptional, (37 reviews)
"The Beacon Hill studio made for an excellent pied de terre for our weekend in Boston."
United States
Heather B.
The price is CA $268
CA $493 total
includes taxes & fees
Nov 25 - Nov 26
Gorgeous Beacon Hills Studio next to State house

20. Skylit Suite in Musical home

Skylit Suite in Musical home
Roxbury
9.6 out of 10, Exceptional, (15 reviews)
"The property was well furnished and had all the amenities we needed. "
United States
Anonymous traveller
The price is CA $282
CA $572 total
includes taxes & fees
Nov 16 - Nov 17
Skylit Suite in Musical home
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

Find out more about Winthrop

Winthrop Vacation Homes information

Number of reviews
177
Accommodation
576 Vacation Homes
Lowest Price
CA $292
Highest Price
CA $1,030

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