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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Winchester vacation homes

Exterior detail

3BR pet-friendly Quincy house w/parking — near Adams Park

3BR pet-friendly Quincy house w/parking — near Adams Park
Quincy
9.8 out of 10, Exceptional, (47 reviews)
"very clean. comfortable beds. Very nice stay."
Germany
Stefanie K.
The price is AED 397
AED 1,067 total
includes taxes & fees
29 Mar - 30 Mar
3BR pet-friendly Quincy house w/parking — near Adams Park
TV

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, (13 reviews)
"Nice visit"
United States
Nate P.
The price is AED 417
AED 1,208 total
includes taxes & fees
25 Mar - 26 Mar
Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking
Living area

Just Ducky: Lake Front, Easy Access to Boston, Mobility Friendly

Just Ducky: Lake Front, Easy Access to Boston, Mobility Friendly
Wilmington
The price is AED 523
AED 2,309 total
includes taxes & fees
24 Mar - 25 Mar
Just Ducky: Lake Front, Easy Access to Boston, Mobility Friendly
Interior

Charming 2-bedroom building in delightful Hull with ocean view

Charming 2-bedroom building in delightful Hull with ocean view
Nantasket Beach
9.6 out of 10, Exceptional, (5 reviews)
"Stayed with family for a wedding reception close by. Location is outstanding. Walkable to all the beach restaurants and beach. "
United States
Sarah S.
The price is AED 731
AED 1,309 total
includes taxes & fees
29 Mar - 30 Mar
Charming 2-bedroom building in delightful Hull with ocean view
Smart TV

37 - 3BR Quincy - Cozy Townhouse near Adams Park

37 - 3BR Quincy - Cozy Townhouse near Adams Park
Quincy
9.0 out of 10, Wonderful, (37 reviews)
"Enjoyed our stay. Clean and comfortable"
United States
maureen g.
The price is AED 362
AED 1,012 total
includes taxes & fees
24 Mar - 25 Mar
37 - 3BR Quincy - Cozy Townhouse near Adams Park
Iron/ironing board, WiFi, bed sheets

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

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Dorchester
9.0 out of 10, Wonderful, (2 reviews)
"Easy check-in, and the host was available to assist with any needs. Space was nice and cozy. Also, the view from the top floor was pretty dope. Will definitely book again."
United States
Breshan B.
The price is AED 434
AED 710 total
includes taxes & fees
24 Mar - 25 Mar
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
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, (33 reviews)
"Loved the private outdoor patio"
United States
Robin P.
The price is AED 691
AED 1,297 total
includes taxes & fees
5 Apr - 6 Apr
Gorgeous Beacon Hills Studio next to State house
Fridge, dishwasher, cookware/dishes/utensils

PEACEFUL CHARM - Humble Luxury minutes from Boston, Beach & Casino

PEACEFUL CHARM - Humble Luxury minutes from Boston, Beach & Casino
Everett
9.2 out of 10, Wonderful, (5 reviews)
"This is a fantastic home with a lot of amenities. Barry, the host, was awesome to work with and went above and beyond to make our stay perfect. "
United States
Deanna K.
The price is AED 591
AED 1,148 total
includes taxes & fees
24 Mar - 25 Mar
PEACEFUL CHARM - Humble Luxury minutes from Boston, Beach & Casino
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 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 AED 625
AED 1,502 total
includes taxes & fees
24 Mar - 25 Mar
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
On the beach

*Salem Spooky 2BR Downtown| Halloween+Hocus Pocus

*Salem Spooky 2BR Downtown| Halloween+Hocus Pocus
Salem
9.2 out of 10, Wonderful, (51 reviews)
"Cute place! Perfect size for our group of 3 adults. Kitchen was nicely equiped. Everything is within walking distance from the house. The cons of this house are the small bathrooms and the upstairs neighbors can be heard all hours of the day and night."
United States
Shannon S.
The price is AED 500
AED 1,130 total
includes taxes & fees
26 Mar - 27 Mar
*Salem Spooky 2BR Downtown| Halloween+Hocus Pocus
Exterior

Cozy Large House close to TUFTS/Harvard/MIT 4BR

Cozy Large House close to TUFTS/Harvard/MIT 4BR
South Medford
9.6 out of 10, Exceptional, (8 reviews)
"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.
The price is AED 562
AED 1,726 total
includes taxes & fees
24 Mar - 25 Mar
Cozy Large House close to TUFTS/Harvard/MIT 4BR
Fridge, microwave, oven, stovetop

Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!

Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!
Marblehead
10.0 out of 10, Exceptional, (27 reviews)
"great place and location"
United States
Kacey C.
The price is AED 886
AED 1,601 total
includes taxes & fees
26 Mar - 27 Mar
Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!
Interior

HOLIDAY GETAWAY SPECIAL -EARLY BIRD 10% 39 - Modern 3BR Quincy near Adams

HOLIDAY GETAWAY SPECIAL -EARLY BIRD 10% 39 - Modern 3BR Quincy near Adams
Quincy
9.8 out of 10, Exceptional, (51 reviews)
"Very clean and stay was enjoyable. "
United States
Sheldon S.
The price is AED 362
AED 1,028 total
includes taxes & fees
24 Mar - 25 Mar
HOLIDAY GETAWAY SPECIAL -EARLY BIRD 10% 39 - Modern 3BR Quincy near Adams
Interior

Renovated Beach House Close to Everything, Minutes to Boston

Renovated Beach House Close to Everything, Minutes to Boston
Quincy
9.4 out of 10, Exceptional, (107 reviews)
"House was very clean and spacious. Easy and quick commute to downtown Boston. "
United States
Greg S.
The price is AED 661
AED 1,543 total
includes taxes & fees
25 Mar - 26 Mar
Renovated Beach House Close to Everything, Minutes to Boston
3 bedrooms, desk, iron/ironing board, free WiFi

Cozy three-bedroom home close to Boston w/ plenty of parking

Cozy three-bedroom home close to Boston w/ plenty of parking
North Braintree
10.0 out of 10, Exceptional, (46 reviews)
"The house was just what we needed and the stay was super simple. "
United States
Chris B.
The price is AED 810
AED 1,713 total
includes taxes & fees
24 Mar - 25 Mar
Cozy three-bedroom home close to Boston w/ plenty of parking
Interior

41 - 3BR Quincy - Lovely Townhouse near Adams

41 - 3BR Quincy - Lovely Townhouse near Adams
Quincy
9.4 out of 10, Exceptional, (26 reviews)
"We enjoyed our stay at this place. Comfortable and plenty of space for us."
United States
Jeff L.
The price is AED 362
AED 1,028 total
includes taxes & fees
24 Mar - 25 Mar
41 - 3BR Quincy - Lovely Townhouse near Adams
Dining

Nothing Fancy Older Pet Friendly Home – near I-95

Nothing Fancy Older Pet Friendly Home – near I-95
Georgetown
9.4 out of 10, Exceptional, (3 reviews)
"Came for a short stay and had absolutely no complaints. Easy entry, great communication and an amazing home to stay in. Would highly recommend:)"
United States
Fedalis R.
The price is AED 367
AED 1,079 total
includes taxes & fees
24 Mar - 25 Mar
Nothing Fancy Older Pet Friendly Home – near I-95
Microwave, oven, stovetop, dishwasher

Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams

Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams
Quincy
10.0 out of 10, Exceptional, (1 review)
"Nice amount of room and overall cleanliness."
United States
Jodi A.
The price is AED 606
AED 1,050 total
includes taxes & fees
30 Mar - 31 Mar
Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams
Fridge, microwave, oven, stovetop

2 bedroom's 1 bathroom 10 min-Airport/Downtown Boston 7 min-Encore Casino

2 bedroom's 1 bathroom 10 min-Airport/Downtown Boston 7 min-Encore Casino
Everett
10.0 out of 10, Exceptional, (6 reviews)
"Great neighborhood! House is beautiful and alot bigger then expected! If we ever get back to the area, this would be my first pick to stay. "
United States
Danielle s.
The price is AED 628
AED 1,346 total
includes taxes & fees
24 Mar - 25 Mar
2 bedroom's 1 bathroom 10 min-Airport/Downtown Boston 7 min-Encore Casino
Fridge, microwave, oven, stovetop

Lake Access 4 Bed 3 Full Bath

Lake Access 4 Bed 3 Full Bath
Billerica
9.8 out of 10, Exceptional, (22 reviews)
"The house was perfect for us! Sparkling clean and comfortable. We really enjoyed staying here and would stay again for sure!"
United States
Diane B.
The price is AED 1,041
AED 2,662 total
includes taxes & fees
24 Mar - 25 Mar
Lake Access 4 Bed 3 Full Bath
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

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

10/10 Excellent
"Really enjoyed our stay! The hotel is located perfectly to be able to explore the city by walking. Lots of great restaurant options nearby for dine-in or takeout. Was well situated to stop back into the hotel and rest for a half hour before venturing back out for the second half of the day. Will definitely be back! Loved the water station on each floor too"
Shaye 3-night trip
Posted less than an hour ago
Club Quarters Hotel Faneuil Hall, Boston

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