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Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21
In one month
Jan 2 - Jan 4
In two months
Jan 30 - Feb 1

Vacation Homes in Winthrop

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

Vacation Home in Marblehead

2.0 star property
10.0 out of 10, Exceptional, (18)
"Enjoyed our stay. "
United States
Mary D.
$311 nightly
The price is $347
Dec 8 - Dec 9
Total with taxes and fees
2BR Historic Marblehead Home+Minutes to Beach
Terrace/patio
Gorgeous Beacon Hills Studio next to State house

Vacation Home in Beacon Hill

9.8 out of 10, Exceptional, (30)
"great room and better location "
United States
jonathan C.
$304 nightly
The price is $350
Dec 7 - Dec 8
Total with taxes and fees
Gorgeous Beacon Hills Studio next to State house
TV
LUXE 4BDR/2BA Near Boston- T-Station & Encore Casino

Vacation Home in East Somerville

10.0 out of 10, Exceptional, (2)
"Great stay and host was very responsive to any questions. "
United States
Matt R.
$253 nightly
The price is $283
Dec 7 - Dec 8
Total with taxes and fees
LUXE 4BDR/2BA Near Boston- T-Station & Encore Casino
Property grounds
Entire 4BR 2 Bath Home l Minutes to Downtown Salem

Vacation Home in Salem

2.0 star property
10.0 out of 10, Exceptional, (18)
"Stayed here with the family for a wedding and then stuck around a couple days to see the sights. Wonderful location since we were able to walk almost everywhere we wanted to go. "
United States
Nancy B.
$357 nightly
The price is $399
Dec 8 - Dec 9
Total with taxes and fees
Entire 4BR 2 Bath Home l Minutes to Downtown Salem
Sun loungers, beach towels
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

Vacation Home in 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.
$376 nightly
The price is $413
Dec 8 - Dec 9
Total with taxes and fees
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
Fridge, microwave, oven, stovetop
Historic 1686 Home Near Downtown l 5BR Retreat

Vacation Home in Beverly

2.0 star property
9.4 out of 10, Exceptional, (13)
"The house was perfect "
United States
Patrick J.
$465 nightly
The price is $519
Dec 9 - Dec 10
Total with taxes and fees
Historic 1686 Home Near Downtown l 5BR Retreat
Interior
3BR3Bth Entire House/Steps to Downtown & TD Garden

Vacation Home in 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.
$541 nightly
The price is $622
Dec 14 - Dec 15
Total with taxes and fees
3BR3Bth Entire House/Steps to Downtown & TD Garden
Exterior
Cozy Large House close to TUFTS/Harvard/MIT 4BR

Vacation Home in 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.
$499 nightly
The price is $541
Dec 7 - Dec 8
Total with taxes and fees
Cozy Large House close to TUFTS/Harvard/MIT 4BR
Beach
Beautiful Hill top 2BR Near Boston & Salem

Vacation Home in Lynn

2.0 star property
$165 nightly
The price is $181
Jan 4 - Jan 5, 2026
Total with taxes and fees
Beautiful Hill top 2BR Near Boston & Salem
Beach
Spectacular Ocean Sunsets I Pet Friendly

Vacation Home in Weymouth

9.4 out of 10, Exceptional, (3)
"We had a wonderful stay in this beautiful spot!"
United States
Laura A.
$394 nightly
The price is $432
Dec 7 - Dec 8
Total with taxes and fees
Spectacular Ocean Sunsets I Pet Friendly
Fridge, microwave, oven, stovetop
39 - 3BR - Quincy Stunning Townhouse near Adams

Vacation Home in Quincy

9.6 out of 10, Exceptional, (50)
"Very clean and stay was enjoyable. "
United States
Sheldon S.
$264 nightly
The price is $295
Dec 8 - Dec 9
Total with taxes and fees
39 - 3BR - Quincy Stunning Townhouse near Adams
Property grounds
383 - 3BR - Quincy Chic House near Adams Park

Vacation Home in 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.
$283 nightly
The price is $316
Dec 10 - Dec 11
Total with taxes and fees
383 - 3BR - Quincy Chic House near Adams Park
Fridge, microwave, oven, stovetop
Moody Salem Home Away From Home

Vacation Home in Salem

9.8 out of 10, Exceptional, (21)
"The house was clean and perfect for my husband and i. The hosts was very accommodating and answerd right away when asked any questions. It really was a home away from home. Walking distance to everything in Salem. Would stay there again. "
United States
Brandy
$236 nightly
The price is $264
Dec 14 - Dec 15
Total with taxes and fees
Moody Salem Home Away From Home
Interior
Charming garden level 1 bedroom 1 bath apartment in Brockton

Vacation Home in Brockton

7.6 out of 10, Good, (8)
"Easy to find, very comfortable, clean and convenient"
United States
David W.
$141 nightly
The price is $157
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming garden level 1 bedroom 1 bath apartment in Brockton
Fridge, microwave, oven, stovetop
Lake Access 4 Bed 3 Full Bath

Vacation Home in Billerica

9.8 out of 10, Exceptional, (20)
"A spacious recently remolded house. Nice common areas and large bedrooms. (Could use more furniture in the bedrooms. :). "
United States
scott r.
$616 nightly
The price is $661
Dec 7 - Dec 8
Total with taxes and fees
Lake Access 4 Bed 3 Full Bath
Fridge, microwave, oven, stovetop
LUXE 3BR Near Boston, Airport, and Beach!

Vacation Home in 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.
$274 nightly
The price is $306
Dec 14 - Dec 15
Total with taxes and fees
LUXE 3BR Near Boston, Airport, and Beach!
Interior
Hidden Gem right in the city of Boston!

Vacation Home in 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.
$339 nightly
The price is $389
Dec 16 - Dec 17
Total with taxes and fees
Hidden Gem right in the city of Boston!
View from property
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

Vacation Home in Marblehead

2.0 star property
9.6 out of 10, Exceptional, (15)
"Beautiful house with gorgeous views and a wonderful park in the back yard. Every night we watched the sun set from the back porches, the kids had a great time exploring the park, and everything was clean and comfortable. Just a lovely place to stay."
United States
Christina J.
$485 nightly
The price is $542
Dec 8 - Dec 9
Total with taxes and fees
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
Property grounds
Charming 2-bedroom building in delightful Hull with ocean view

Vacation Home in Nantasket Beach

9.6 out of 10, Exceptional, (5)
"Stayed with family for a wedding reception close by. Location is outstanding. Walkable to all the beach restaurants and beach. "
United States
Sarah S.
$250 nightly
The price is $279
Jan 5 - Jan 6, 2026
Total with taxes and fees
Charming 2-bedroom building in delightful Hull with ocean view
Fridge, microwave, oven, stovetop
Enchanting Hidden Door Escape

Vacation Home in Stoneham

2.0 star property
9.8 out of 10, Exceptional, (24)
"Great house and location for what our family needed for our recent trip! "
United States
Jenifer H.
$549 nightly
The price is $591
Dec 7 - Dec 8
Total with taxes and fees
Enchanting Hidden Door Escape
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 Dagny Boston

The Dagny Boston

10/10 Excellent
"Hi, enjoyed the stay. Staff was excellent and room was clean. Restaurant was good. "
Mike 2-night trip
Posted 13 hours ago
The Dagny Boston

Find out more about Winthrop

Winthrop Vacation Homes information

Number of reviews
318
Accommodation
607 Vacation Homes
Lowest Price
$157
Highest Price
$661

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