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Dec 12 - Dec 14
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Jan 30 - Feb 1

Vacation Homes in Winchester

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

2BR Historic Marblehead Home+Minutes to Beach

2.0 star property
Marblehead
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

Gorgeous Beacon Hills Studio next to State house

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
Sun loungers, beach towels
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, (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 3 - Dec 4
Total with taxes and fees
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
On the beach
*NEW Spooky Halloween 2BR|Downtown|Parking

*NEW Spooky Halloween 2BR|Downtown|Parking

Salem
9.2 out of 10, Wonderful, (47)
"Very clean, quiet and convenient location! The owners checked in with me through the app to make sure we had everything we needed. I would stay again!"
United States
Rebecca T.
$256 nightly
The price is $293
Dec 3 - Dec 4
Total with taxes and fees
*NEW Spooky Halloween 2BR|Downtown|Parking
Property grounds
Entire 4BR 2 Bath Home l Minutes to Downtown Salem

Entire 4BR 2 Bath Home l Minutes to Downtown Salem

2.0 star property
Salem
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.
$368 nightly
The price is $411
Dec 4 - Dec 5
Total with taxes and fees
Entire 4BR 2 Bath Home l Minutes to Downtown Salem
Outdoor dining
Nothing Fancy Older Pet Friendly Home – near I-95

Nothing Fancy Older Pet Friendly Home – near I-95

Georgetown
9.0 out of 10, Wonderful, (2)
"Such a great place! Lots of room, beautiful backyard, and quiet. Perfect for relaxing after a day of exploring. We would love to stay again! "
United States
Megan H.
$278 nightly
The price is $294
Dec 4 - Dec 5
Total with taxes and fees
Nothing Fancy Older Pet Friendly Home – near I-95
Interior
3BR3Bth Entire House/Steps to Downtown & TD Garden

3BR3Bth Entire House/Steps to Downtown & TD Garden

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.
$599 nightly
The price is $689
Dec 14 - Dec 15
Total with taxes and fees
3BR3Bth Entire House/Steps to Downtown & TD Garden
Fridge, microwave, oven, stovetop
39 - 3BR - Quincy Stunning Townhouse near Adams

39 - 3BR - Quincy Stunning Townhouse near Adams

Quincy
9.6 out of 10, Exceptional, (50)
"Very clean and stay was enjoyable. "
United States
Sheldon S.
$283 nightly
The price is $316
Dec 3 - Dec 4
Total with taxes and fees
39 - 3BR - Quincy Stunning Townhouse near Adams
Interior
Hidden Gem right in the city of Boston!

Hidden Gem right in the city of Boston!

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.
$354 nightly
The price is $407
Dec 16 - Dec 17
Total with taxes and fees
Hidden Gem right in the city of Boston!
Property grounds
383 - 3BR - Quincy Chic House near Adams Park

383 - 3BR - Quincy Chic House near Adams Park

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.
$275 nightly
The price is $307
Dec 3 - Dec 4
Total with taxes and fees
383 - 3BR - Quincy Chic House near Adams Park
Fridge, microwave, oven, stovetop
Moody Salem Home Away From Home

Moody Salem Home Away From Home

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 7 - Dec 8
Total with taxes and fees
Moody Salem Home Away From Home
Stereo
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, (2)
"We went to a concert at TD Gardens and this place was perfect for 2 couples in close proximity!"
United States
Chelsea J.
$324 nightly
The price is $339
Dec 9 - Dec 10
Total with taxes and fees
PEACE IN THE CITY - Humble Luxury minutes from Boston, Beach & Casino
4 bedrooms, desk, iron/ironing board, travel crib
Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area

Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area

Dorchester
9.6 out of 10, Exceptional, (14)
"Amazing location close to everything you are going to want to see in Boston, and great communication with the host."
United States
Shane M.
$352 nightly
The price is $404
Dec 8 - Dec 9
Total with taxes and fees
Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area
Beach
Beautiful Hill top 2BR Near Boston & Salem

Beautiful Hill top 2BR Near Boston & Salem

2.0 star property
Lynn
$167 nightly
The price is $184
Dec 3 - Dec 4
Total with taxes and fees
Beautiful Hill top 2BR Near Boston & Salem
Fridge, microwave, oven, stovetop
Centrally located in the heart of Boston near T

Centrally located in the heart of Boston near T

Dorchester
9.0 out of 10, Wonderful, (20)
"Made our way from Tx to Boston to beat the heat…unfortunately we brought a record breaking heat wave with us. Nice space. As advertised, clean and spacious. Really happy the a/c was able to keep up with the weather. Short walk to restaurants, bars, and the T station made this an affordable and convenient spot to explore Boston. "
United States
Geoffrey P.
$440 nightly
The price is $506
Dec 3 - Dec 4
Total with taxes and fees
Centrally located in the heart of Boston near T
Fridge, microwave, oven, stovetop
17 - 4BR Randolph - Cozy Single House

17 - 4BR Randolph - Cozy Single House

Randolph
10.0 out of 10, Exceptional, (2)
"It was a cozy and clean home with everything needed to accommodate your stay. My family and young nephews had a great time here and I’d recommend it to anyone looking to visit Boston"
United States
Nicholas P.
$340 nightly
The price is $380
Dec 3 - Dec 4
Total with taxes and fees
17 - 4BR Randolph - Cozy Single House
Fridge, microwave, oven, stovetop
LUXE 3BR Near Boston, Airport, and Beach!

LUXE 3BR Near Boston, Airport, and Beach!

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!
TV
LUXE 4BDR/2BA Near Boston- T-Station & Encore Casino

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

East Somerville
$258 nightly
The price is $289
Dec 3 - Dec 4
Total with taxes and fees
LUXE 4BDR/2BA Near Boston- T-Station & Encore Casino
Fridge, microwave, oven, stovetop
Historic 1686 Home Near Downtown l 5BR Retreat

Historic 1686 Home Near Downtown l 5BR Retreat

2.0 star property
Beverly
9.4 out of 10, Exceptional, (13)
"The house was perfect "
United States
Patrick J.
$511 nightly
The price is $571
Dec 7 - Dec 8
Total with taxes and fees
Historic 1686 Home Near Downtown l 5BR Retreat
Exterior
✨Private Studio w/ Loft Center Historic Carlisle✨

✨Private Studio w/ Loft Center Historic Carlisle✨

Carlisle
9.4 out of 10, Exceptional, (33)
"We had a great stay! The place was perfect for our weekend trip. We were able to hit all of the spots we planned, with the central location!"
United States
C Z.
$169 nightly
The price is $179
Dec 3 - Dec 4
Total with taxes and fees
✨Private Studio w/ Loft Center Historic Carlisle✨
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 Winchester Hotel Reviews

Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"From valet to the front desk staff and the turn down service this is a hotel that will become a go to for our family vacations. Higgly recommend!"
Noelle 2-night trip
Posted 11 hours ago
Seaport Hotel Boston

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
351
Accommodation
548 Vacation Homes
Lowest Price
$179
Highest Price
$689

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