Sunny 3 bedroom by the sea in scenic Winthrop with home town charm.

Sleeps 10

10
bedrooms

3
bathroom

1

3 BR
1 BA
Sleeps 10

$500

avg/night

Boston Harbor Two Bedroom Waterfront Home

Sleeps 4

4
bedrooms

2
bathroom

1

2 BR
1 BA
Sleeps 4

$3,000

avg/night

Viewed 37 times in the last 48 hours

Contemporary Style And Comfort Convenient To Boston And Route 128

Sleeps 2

2
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 2

Wonderful! 4.9/5
(16 reviews)

$114

avg/night

Viewed 49 times in the last 48 hours

Sweeping Harbor Views, Antique Charm And First Class Amenities In Old Town

Sleeps 4

4
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 4

Wonderful! 4.9/5
(36 reviews)

$160

avg/night

Viewed 11 times in the last 48 hours

Handsome, Homey, V. Clean!, 1 Bedroom Unit, 2 Min Walk To Ocean!

Sleeps 2

2
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 2

Excellent! 4.7/5
(18 reviews)

$133

avg/night

Viewed 58 times in the last 48 hours

Charming, Antique Home In The Heart Of Historic Salem

Sleeps 4

4
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 4

Wonderful! 4.9/5
(90 reviews)

$136

avg/night

Viewed 55 times in the last 48 hours

Charming One Bedroom Condo Located In Beacon Hill - Newly Renovated

Sleeps 2

2
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 2

Wonderful! 4.9/5
(33 reviews)

$214

avg/night

Viewed 28 times in the last 48 hours

Spring is coming Book now and Boston Is 12 Minutes Away

Sleeps 4

4
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 4

Excellent! 4.7/5
(10 reviews)

$93

avg/night

Viewed 29 times in the last 48 hours

Beautiful Beacon Hill! Prestigious, historic heart of Boston! Sweet 1-bd condo.

Sleeps 4

4
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 4

Wonderful! 4.9/5
(124 reviews)

$209

avg/night

124

Viewed 39 times in the last 48 hours

Steps from Scituate Lighthouse, near harbor and beaches

Sleeps 4

4
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 4

Excellent! 4.7/5
(42 reviews)

$118

avg/night

Viewed 62 times in the last 48 hours

Top rated in Boston: 1 Bedroom hideaway on Beacon Hill!

Sleeps 4

4
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 4

Wonderful! 4.8/5
(73 reviews)

$185

avg/night

Viewed 54 times in the last 48 hours

SUNNY AND COZY 2 BEDROOM DUPLEX, JAMAICA PLAIN, BOSTON

Sleeps 6

6
bedrooms

2
bathroom

1

2 BR
1 BA
Sleeps 6

Wonderful! 4.8/5
(60 reviews)

$159

avg/night

Viewed 57 times in the last 48 hours

NORTH END ENCHANTED COTTAGE VACATION RENTAL 18 out of 18 FIVE STAR reviews

Sleeps 2

2
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 2

Exceptional! 5/5
(18 reviews)

$190

avg/night

Viewed 35 times in the last 48 hours

Stylish 3-Bdrm Beacon Hill Condo, Next to Charles St, Boston Common

Sleeps 5

5
bedrooms

3
bathroom

1

3 BR
1 BA
Sleeps 5

Wonderful! 4.9/5
(125 reviews)

$374

avg/night

125

Viewed 17 times in the last 48 hours

Chic, stylish 1 BD Condo in the prestigious Bellevue Hotel on Beacon Hill

Sleeps 4

4
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 4

Wonderful! 4.8/5
(55 reviews)

$225

avg/night

Viewed 29 times in the last 48 hours

Charming Nantasket Beach House

Sleeps 4

4
bedrooms

2
bathroom

1

2 BR
1 BA
Sleeps 4

Wonderful! 4.8/5
(12 reviews)

$129

avg/night

Viewed 37 times in the last 48 hours

Romantic Ocean & Boston Skyline Views

Sleeps 2

2
bedroom

1
bathroom

1
HF BA

1

1 BR
1 BA
1 HF BA
Sleeps 2

Wonderful! 4.9/5
(70 reviews)

$158

avg/night

Viewed 103 times in the last 48 hours

Boston Harbor Yacht, Skyline view, Free Parking, AC/Heat, Walk to North End WiFi

Sleeps 6

6
bedrooms

2
bathrooms

2

2 BR
2 BA
Sleeps 6

Wonderful! 4.8/5
(32 reviews)

$283

avg/night

Viewed 32 times in the last 48 hours

Back Bay Boston Furnished Apartment Rental - 387 Commonwealth Avenue Unit 2

Sleeps 6

6
bedrooms

3
bathroom

1

3 BR
1 BA
Sleeps 6

$340

avg/night

Viewed 36 times in the last 48 hours

Wonderful Jamaica Plain location, steps from T

Sleeps 4

4
bedroom

1
bathrooms

2

1 BR
2 BA
Sleeps 4

Excellent! 4.6/5
(57 reviews)

$134

avg/night

Viewed 22 times in the last 48 hours

Spacious Bright 2 Bedroom Sleeps 4 walking distance to everything

Sleeps 6

6
bedrooms

2
bathroom

1

2 BR
1 BA
Sleeps 6

Very Good! 4.1/5
(8 reviews)

$75

avg/night

Viewed 44 times in the last 48 hours

WALK TO FANUEIL HALL, 4 bedroom Historic Brick Townhome on Gas lit street

Sleeps 8

8
bedrooms

4
bathrooms

2
HF BA

1

4 BR
2 BA
1 HF BA
Sleeps 8

Wonderful! 4.9/5
(24 reviews)

$600

avg/night

Viewed 29 times in the last 48 hours

Boston's Most Charming Bed & Breakfast - Heart of the City

Sleeps 4

4
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 4

Excellent! 4.5/5
(26 reviews)

$220

avg/night

Viewed 36 times in the last 48 hours

The Perfect Location to Explore Boston

Sleeps 4

4
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 4

Wonderful! 4.9/5
(136 reviews)

$250

avg/night

136

Viewed 29 times in the last 48 hours

Beacon Hill -- Sunny Studio ('the Nest')

Sleeps 2

2
bedrooms

Studio
bathroom

1

Studio
1 BA
Sleeps 2

Exceptional! 5/5
(21 reviews)

$200

avg/night

Viewed 37 times in the last 48 hours

Spectacular South End Two Floor Penthouse with a View

Sleeps 6

6
bedrooms

2
bathroom

1

2 BR
1 BA
Sleeps 6

Wonderful! 4.8/5
(31 reviews)

$420

avg/night

Viewed 29 times in the last 48 hours

Luxurious house close to Boston, airport & train

Sleeps 9

9
bedrooms

4
bathrooms

2

4 BR
2 BA
Sleeps 9

Exceptional! 5/5
(43 reviews)

$350

avg/night

Viewed 77 times in the last 48 hours

Furnished 2.5BR / 1 BA Apartment in Boston!

Sleeps 7

7
bedrooms

2
bathroom

1

2 BR
1 BA
Sleeps 7

Excellent! 4.5/5
(40 reviews)

$141

avg/night

Viewed 74 times in the last 48 hours

Amazing Garrison Street Apartment

Sleeps 5

5
bedrooms

2
bathrooms

2

2 BR
2 BA
Sleeps 5

Wonderful! 4.8/5
(97 reviews)

$325

avg/night

Viewed 19 times in the last 48 hours

2BR Boston Condo In the Heart of Back Bay w/Wifi!

Sleeps 4

4
bedrooms

2
bathrooms

2

2 BR
2 BA
Sleeps 4

Excellent! 4.6/5
(18 reviews)

$240

avg/night

Viewed 13 times in the last 48 hours

3 BR/ 3 BATH in Historic Home Mins. from Kendall Sq. , MIT, Harvard & Boston

Sleeps 8

8
bedrooms

3
bathrooms

3

3 BR
3 BA
Sleeps 8

Exceptional! 5/5
(10 reviews)

$500

avg/night

Sunny 2 Bedroom Back Bay Condo

Sleeps 4

4
bedrooms

2
bathroom

1

2 BR
1 BA
Sleeps 4

$357

avg/night

Viewed 38 times in the last 48 hours

Historic North End Boston & Waterfront & Fanueil Hall - walk to everything

Sleeps 4

4
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 4

Excellent! 4.6/5
(59 reviews)

$186

avg/night

Viewed 24 times in the last 48 hours

Heart of Boston - Beacon Hill

Sleeps 4

4
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 4

Wonderful! 4.9/5
(66 reviews)

$202

avg/night

Viewed 12 times in the last 48 hours

Private apt. W/Kitchen Near M.I.T., Harvard,

Sleeps 3

3
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 3

Very Good! 4.1/5
(11 reviews)

$210

avg/night

Viewed 32 times in the last 48 hours

Beautiful, Renovated Beacon Hill Condo

Sleeps 3

3
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 3

Wonderful! 4.9/5
(20 reviews)

$207

avg/night

Viewed 8 times in the last 48 hours

Guest House at Hooper

Sleeps 4

4
bedrooms

2
bathroom

1

2 BR
1 BA
Sleeps 4

Wonderful! 4.9/5
(58 reviews)

$143

avg/night

Viewed 26 times in the last 48 hours

Beautiful Sunny Two Bedroom in Historic Beacon Hill

Sleeps 4

4
bedrooms

2
bathroom

1

2 BR
1 BA
Sleeps 4

Excellent! 4.6/5
(59 reviews)

$365

avg/night

Viewed 21 times in the last 48 hours

Your Source for Charming, Personal Accommodations in Boston

Sleeps 6

6
bedrooms

3
bathrooms

2

3 BR
2 BA
Sleeps 6

Excellent! 4.7/5
(38 reviews)

$430

avg/night

Viewed 35 times in the last 48 hours

Spactacular, Luxurious Faneuil Hall 2 bedroom 2 Bath condo

Sleeps 6

6
bedrooms

2
bathroom

1

2 BR
1 BA
Sleeps 6

Exceptional! 5/5
(9 reviews)

$438

avg/night

Viewed 31 times in the last 48 hours

UltraLuxe Apt in Boston Brownstone2 in Prime Location

Sleeps 8

8
bedrooms

4
bathrooms

4

4 BR
4 BA
Sleeps 8

Exceptional! 5/5
(21 reviews)

$642

avg/night

Viewed 30 times in the last 48 hours

Up-to-date furnishings in a 1920s house.

Sleeps 8

8
bedrooms

3
bathroom

1

3 BR
1 BA
Sleeps 8

Wonderful! 4.9/5
(97 reviews)

$275

avg/night

Viewed 27 times in the last 48 hours

UltraLuxe Apt in Boston Brownstone in Prime Area

Sleeps 8

8
bedrooms

4
bathrooms

4
HF BA

1

4 BR
4 BA
1 HF BA
Sleeps 8

Wonderful! 4.9/5
(31 reviews)

$649

avg/night

Viewed 35 times in the last 48 hours

Entire Private 2Bd Apartment/Condo Near Airport Blue Line Train Station Boston

Sleeps 6

6
bedrooms

2
bathroom

1

2 BR
1 BA
Sleeps 6

Excellent! 4.7/5
(38 reviews)

$225

avg/night

Viewed 46 times in the last 48 hours

Entire Luxurious Private 2Bd Apartment/Condo Near Airport Train Station Boston

Sleeps 5

5
bedrooms

2
bathroom

1

2 BR
1 BA
Sleeps 5

Excellent! 4.4/5
(40 reviews)

$211

avg/night

Viewed 11 times in the last 48 hours

Newly Renovated Charming apartment in Cambridge

Sleeps 4

4
bedrooms

2
bathroom

1
HF BA

1

2 BR
1 BA
1 HF BA
Sleeps 4

Wonderful! 4.8/5
(12 reviews)

$301

avg/night

Viewed 18 times in the last 48 hours

Perfect View of Marblehead Harbor

Sleeps 3

3
bedrooms

2
bathroom

1

2 BR
1 BA
Sleeps 3

Wonderful! 4.9/5
(47 reviews)

$136

avg/night

Viewed 6 times in the last 48 hours

COMFORTABLE AND WELL-APPOINTED, BRIGHT AND SPACIOUS ON THE BOSTON-CAMBRIDGE LINE

Sleeps 4

4
bedrooms

2
bathroom

1

2 BR
1 BA
Sleeps 4

Exceptional! 5/5
(29 reviews)

$243

avg/night

Viewed 12 times in the last 48 hours

Panoramic view of harbor from roof deck

Sleeps 3

3
bedroom

1
bathroom

1

1 BR
1 BA
Sleeps 3

Wonderful! 4.9/5
(41 reviews)

$136

avg/night

Viewed 17 times in the last 48 hours

Charming Harvard Square Studio

Sleeps 2

2
bedrooms

Studio
bathroom

1

Studio
1 BA
Sleeps 2

Wonderful! 4.9/5
(26 reviews)

$135

avg/night

Winthrop (300+)

Recent Winthrop Reviews

View property

My husband and I enjoyed our long weekend on the Sea Pearl. The marina was nice and quiet and the few people we saw there were friendly. (I believe Deb also rents out the Little Pearl, a 1 bedroom boat docked next to the Sea Pearl.) You are close enough to walk to a few attractions (USS Constitution, Bunker Hill Monument), but we used the water taxi and Uber to visit attractions farther away (other locations along the Freedom Trail) and to go out to eat in the North End and Seaport. For those interested in the duck boat tours, note that Super Duck Tours went out of business Fall of 2016. The original tour group, Boston Duck Tours, is still in business. The Sea Pearl was in pretty good shape. The cleaning lady, Sherry, had written down the wrong arrival time of 6pm, so when we arrived at 3:30pm, the boat had not yet been cleaned. She was quick to get it taken care of and orient us to the boat and marina, but we basically had to drop our luggage and find something to do in the meantime. Deb was very apologetic and we appreciated that. Note there are steep steps to enter the boat and also steps within the boat to enter the bedroom/bathroom areas. There is not much in the way of comfortable seating outside the boat, so we didn't really hang out outside. Overall, we were pleased with our stay and would definitely return. Plus, it's just a unique, cool experience!

Submitted: Aug 21, 2017
Stayed: Aug 2017

View property

Great Location and charming place with a lot of character The rooftop deck put the icing on the cake

5 of 5

Every thing was perfect comfortable bed nice kitchen with some essentials already there and amazing views convenient parking space

Submitted: Aug 21, 2017
Stayed: Aug 2017

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Winthrop (300+)

Recent Winthrop Reviews