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Vacation Homes in Winchester

NEW 2BR Historic Marblehead Home+Minutes to Beach

2.0 star property
Marblehead
10.0 out of 10, Exceptional, (17)
"This was a great little house surrounded by history. We had all the amenities we needed and were comfortable. Our host was very responsive and helpful. "
United States
Jeremy T.
The price is AED 459
AED 1,423 total
includes taxes & fees
2 Dec - 3 Dec
NEW 2BR Historic Marblehead Home+Minutes to Beach

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.
The price is AED 731
AED 1,376 total
includes taxes & fees
7 Dec - 8 Dec
Gorgeous Beacon Hills Studio next to State house

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.
The price is AED 992
AED 2,170 total
includes taxes & fees
17 Nov - 18 Nov
3BR3Bth Entire House/Steps to Downtown & TD Garden

Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

Bayside
9.8 out of 10, Exceptional, (14)
"Excellent"
United States
Sandy S.
The price is AED 625
AED 1,475 total
includes taxes & fees
17 Nov - 18 Nov
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

Hidden Gem right in the city of Boston!

Hyde Park
9.6 out of 10, Exceptional, (24)
"We had a wonderful stay. The apartment was exactly as advertised. It’s very clean and in a cute borough with some great restaurants and shops and any other convenience you might need. The apartment has a large kitchen that’s great for cooking your own meals if you wish to do so. Check in was completely seamless even though we were arriving late at night. "
Canada
Penelope M.
The price is AED 476
AED 1,447 total
includes taxes & fees
18 Nov - 19 Nov
Hidden Gem right in the city of Boston!

LUXE 3BR Near Boston, Airport, and Beach!

Revere
9.8 out of 10, Exceptional, (6)
"Loved the property! Would defiantly rent again! "
United States
Jessica C.
The price is AED 335
AED 1,133 total
includes taxes & fees
18 Nov - 19 Nov
LUXE 3BR Near Boston, Airport, and Beach!

Entire 4BR 2 Bath Home l Minutes to Downtown Salem

2.0 star property
Salem
10.0 out of 10, Exceptional, (18)
"Great property. Can walk to many things and was a great hub to see beautiful Maine Owner was helpful and quick to respond. "
United States
Michelle B.
The price is AED 536
AED 1,624 total
includes taxes & fees
8 Dec - 9 Dec
Entire 4BR 2 Bath Home l Minutes to Downtown Salem

Charming 2-bedroom building in delightful Hull with ocean view

Nantasket Beach
9.6 out of 10, Exceptional, (5)
"The property is conveniently located next to the beach and has very nice deck views. The poperty manager was very nice and provided timely support. Highly recommeded!!"
United States
Louay A.
The price is AED 441
AED 919 total
includes taxes & fees
19 Nov - 20 Nov
Charming 2-bedroom building in delightful Hull with ocean view

Lovely 2 bedroom- kitchenette

2.0 star property
Andover
9.2 out of 10, Wonderful, (5)
"Very pretty area and the host was extremely pleasant and communicative "
United States
Allen B.
The price is AED 498
AED 1,762 total
includes taxes & fees
17 Nov - 18 Nov
Lovely 2 bedroom- kitchenette

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.
The price is AED 422
AED 1,150 total
includes taxes & fees
18 Nov - 19 Nov
Nothing Fancy Older Pet Friendly Home – near I-95

Family-Friendly Townhouse on the Merrimack River

Methuen
9.6 out of 10, Exceptional, (14)
"A lovely home on a river. Close to wedding venue, which was wonderful. Very clean home, and owner was quick to respond and welcoming. "
United States
Danielle B.
The price is AED 437
AED 1,120 total
includes taxes & fees
19 Nov - 20 Nov
Family-Friendly Townhouse on the Merrimack River

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
The price is AED 311
AED 983 total
includes taxes & fees
20 Nov - 21 Nov
Moody Salem Home Away From Home

Beautiful Hill top 2BR Near Boston & Salem

2.0 star property
Lynn
Beautiful Hill top 2BR Near Boston & Salem

*Spooky 2BR Halloween|HocusPocus|Parking+Downtown

Salem
9.2 out of 10, Wonderful, (46)
"Great property and close to all the major attractions and shopping."
United States
Christina D.
The price is AED 731
AED 1,432 total
includes taxes & fees
23 Nov - 24 Nov
*Spooky 2BR Halloween|HocusPocus|Parking+Downtown

✨Private Studio w/ Loft Center Historic Carlisle✨

Carlisle
9.4 out of 10, Exceptional, (33)
"Great"
United States
J Rhoads R.
The price is AED 311
AED 600 total
includes taxes & fees
17 Nov - 18 Nov
✨Private Studio w/ Loft Center Historic Carlisle✨

Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking

South Medford
10.0 out of 10, Exceptional, (3)
"Clean rooms and comfortable beds "
United States
camilo r.
The price is AED 430
AED 1,251 total
includes taxes & fees
20 Nov - 21 Nov
Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking

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.
The price is AED 576
AED 1,128 total
includes taxes & fees
17 Nov - 18 Nov
PEACE IN THE CITY - Humble Luxury minutes from Boston, Beach & Casino

383 - 3BR - Quincy Chic House near Adams Park

Quincy
9.6 out of 10, Exceptional, (44)
"House was very clean and spacious. The parking lot has a fabulous waterfall and koi fish feature which was very cool. Nice mattresses and plenty of beds. We enjoyed our quick overnight stay. Would definitely stay again. "
United States
Rich T.
The price is AED 528
AED 1,332 total
includes taxes & fees
17 Nov - 18 Nov
383 - 3BR - Quincy Chic House near Adams Park

Entire Private home 3BDS 1 and half BTHS/ Pet Friendly with fee

Lynn
9.4 out of 10, Exceptional, (3)
"Fantastic! The easiest check in and check out I’ve ever had super clean. So close to everything. Would highly recommend "
United States
Amanda W.
The price is AED 716
AED 1,588 total
includes taxes & fees
24 Nov - 25 Nov
Entire Private home 3BDS 1 and half BTHS/ Pet Friendly with fee

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

East Somerville
The price is AED 309
AED 1,170 total
includes taxes & fees
23 Nov - 24 Nov
LUXE 4BDR/2BA Near Boston- T-Station & Encore Casino
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