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Our top choices for Winchester vacation homes

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, (49 reviews)
"very clean. comfortable beds. Very nice stay."
Germany
Stefanie K.
The price is AED 525
AED 1,230 total
includes taxes & fees
28 Apr - 29 Apr
3BR pet-friendly Quincy house w/parking — near Adams Park

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

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Dorchester
8.8 out of 10, Excellent, (3 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 465
AED 754 total
includes taxes & fees
27 Apr - 28 Apr
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

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 658
AED 1,543 total
includes taxes & fees
27 Apr - 28 Apr
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

2BR Historic Marblehead Home+Minutes to Beach

2BR Historic Marblehead Home+Minutes to Beach
Marblehead Historic District
10.0 out of 10, Exceptional, (20 reviews)
"Enjoyed our stay. "
United States
Mary D.
The price is AED 498
AED 1,410 total
includes taxes & fees
4 May - 5 May
2BR Historic Marblehead Home+Minutes to Beach

37 - 3BR Quincy - Cozy Townhouse near Adams Park

37 - 3BR Quincy - Cozy Townhouse near Adams Park
Quincy
9.2 out of 10, Wonderful, (40 reviews)
"Enjoyed our stay. Clean and comfortable"
United States
maureen g.
The price is AED 525
AED 1,226 total
includes taxes & fees
27 Apr - 28 Apr
37 - 3BR Quincy - Cozy Townhouse near Adams Park

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 602
AED 1,794 total
includes taxes & fees
27 Apr - 28 Apr
Cozy Large House close to TUFTS/Harvard/MIT 4BR

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 808
AED 1,407 total
includes taxes & fees
30 Apr - 1 May
Charming 2-bedroom building in delightful Hull with ocean view

3BR3Bth Entire House/Steps to Downtown & TD Garden

3BR3Bth Entire House/Steps to Downtown & TD Garden
North End
10.0 out of 10, Exceptional, (9 reviews)
"This place is so cool! Was incredibly clean, updated and offered all the amenities you need for a weekend get away. The location is wonderful as well with lots of markets, bakeries and restaurants all within walking distance. This is a must stay! "
United States
mary j.
The price is AED 992
AED 2,255 total
includes taxes & fees
13 May - 14 May
3BR3Bth Entire House/Steps to Downtown & TD Garden

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, (108 reviews)
"Great location, description was on point, and the communication with the owner was excellent. Would definitely stay here again. "
United States
Don T.
The price is AED 628
AED 1,502 total
includes taxes & fees
28 Apr - 29 Apr
Renovated Beach House Close to Everything, Minutes to Boston

Spring Getaway 3BR Townhouse in Boston 41

Spring Getaway 3BR Townhouse in Boston 41
Quincy
9.6 out of 10, Exceptional, (27 reviews)
"We enjoyed our stay at this place. Comfortable and plenty of space for us."
United States
Jeff L.
The price is AED 525
AED 1,226 total
includes taxes & fees
27 Apr - 28 Apr
Spring Getaway 3BR Townhouse in Boston 41

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 663
AED 1,228 total
includes taxes & fees
27 Apr - 28 Apr
PEACEFUL CHARM - Humble Luxury minutes from Boston, Beach & Casino

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 574
AED 2,382 total
includes taxes & fees
9 May - 10 May
Just Ducky: Lake Front, Easy Access to Boston, Mobility Friendly

284 - 5BR Boston-Peaceful House near England Aqua

284 - 5BR Boston-Peaceful House near England Aqua
Quincy
9.8 out of 10, Exceptional, (74 reviews)
"The house is very nice and the layout is great. The third floor is super cool and the house is honestly a great price for what you get. "
United States
Caroline C.
The price is AED 599
AED 1,601 total
includes taxes & fees
27 Apr - 28 Apr
284 - 5BR Boston-Peaceful House near England Aqua

Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
Westwood
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

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, (47 reviews)
"The house was just what we needed and the stay was super simple. "
United States
Chris B.
The price is AED 694
AED 1,633 total
includes taxes & fees
3 May - 4 May
Cozy three-bedroom home close to Boston w/ plenty of parking

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 1,362 total
includes taxes & fees
30 Apr - 1 May
2 bedroom's 1 bathroom 10 min-Airport/Downtown Boston 7 min-Encore Casino

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 1,054 total
includes taxes & fees
5 May - 6 May
Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams

Stylish Boston-Area Duplex - Free Parking, Yard, Comfortable Stay

Stylish Boston-Area Duplex - Free Parking, Yard, Comfortable Stay
Everett
9.4 out of 10, Exceptional, (29 reviews)
"Everything was great for our 2-night stay with 3 adults/3 kids!"
United States
Scott
The price is AED 658
AED 1,580 total
includes taxes & fees
30 Apr - 1 May
Stylish Boston-Area Duplex - Free Parking, Yard, Comfortable Stay

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, (22 reviews)
"Excellent stay! "
United States
Melissa R.
The price is AED 878
AED 1,951 total
includes taxes & fees
3 May - 4 May
Centrally located in the heart of Boston near T

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
Marblehead
9.8 out of 10, Exceptional, (16 reviews)
"We used this lovely home as our hub to explore nearby Salem and really enjoyed the house!We were 3 couples, and had plenty of space to spread out and spend time together. The scenery here just simply can't be beat, and we all wished we could have stayed longer to appreciate the island and the home more."
United States
Remy G.
The price is AED 808
AED 2,134 total
includes taxes & fees
27 Apr - 28 Apr
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
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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