Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for Winchester vacation rentals

Rooftop terrace

Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (618 reviews)
"I can’t recommend The Custom House enough, it is perfect! The staff are wonderful, it’s very clean and the perfect location to see Boston! "
United States
Melissa
The price is ₩302,270
₩347,460 total
includes taxes & fees
Mar 1 - Mar 2
Marriott Vacation Club® at Custom House, Boston
Apartment, 2 Bedrooms | Interior

Furnished Apartment near BMC

Furnished Apartment near BMC
3.0 star property
South End
The price is ₩200,223
₩430,292 total
includes taxes & fees
Feb 22 - Feb 23
Furnished Apartment near BMC
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (332 reviews)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is ₩130,164
₩241,060 total
includes taxes & fees
Feb 23 - Feb 24
Temple Place Suites
Premium Apartment | Living area | 24-inch Smart TV with digital channels

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (28 reviews)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
United States
kelly
The price is ₩229,090
₩521,024 total
includes taxes & fees
Feb 23 - Feb 24
The Chester Hotel
Lobby lounge

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very Good, (662 reviews)
"Everything was great about this place! I will definitely be staying here again!"
United States
Amanda
Global Luxury Suites Downtown Boston
Front of property

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (103 reviews)
"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"
United Kingdom
Jordan Elizabeth Marie
Maverick Suites at 40 Temple St
42-inch TV with satellite channels

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.2 out of 10, Good, (135 reviews)
"everything was great! only thing i’ll say is that the dots have some cracks where people can see in on the bathrooms and some rooms, but other than that i’d start here again!"
United States
Maelynn
Maverick Suites at 400 Columbus Ave
Desk, laptop workspace, free WiFi, bed sheets

Bay Village Suites

Bay Village Suites
2.0 star property
Bay Village
6.6 out of 10, (254 reviews)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites
Apartment (1 Bedroom) | Interior

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
3.0 star property
Lynn
The price is ₩96,900
₩441,098 total
includes taxes & fees
Feb 27 - Feb 28
Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
Apartment | 2 bedrooms, desk

Coastal Charm Lobster Ch Teau

Coastal Charm Lobster Ch Teau
2.0 star property
Swampscott
The price is ₩290,450
₩928,696 total
includes taxes & fees
Feb 22 - Feb 23
Coastal Charm Lobster Ch Teau
Exterior

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very Good, (158 reviews)
"Room was clean and a good size. Location was perfect - walking distance to where I needed to be. "
United States
Steven
Maverick Suites at 245 Newbury St
Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (257 reviews)
"We stayed there for four days. The heaters were not working, I got almost sick. And the customer service was awful. I hope you will find better place to stay"
United States
Aziza
Premier Suites - Bay Village
Premium Studio Suite | Premium bedding, desk, iron/ironing board, free WiFi

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (201 reviews)
"New spot for us in South Bay. Convenient and easy with easy walk to Commonwealth and restaurants of Newbury"
United States
Brian
The price is ₩211,155
₩492,107 total
includes taxes & fees
Feb 23 - Feb 24
Charlesgate Suites
Front of property

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (337 reviews)
"Good place"
United States
Elijah
The price is ₩136,672
₩298,417 total
includes taxes & fees
Mar 1 - Mar 2
Maverick Suites at 28 Fenway
Family Apartment | Living area

3 bd 2 ba Unit

3 bd 2 ba Unit
3.0 star property
East Somerville
The price is ₩516,622
₩794,009 total
includes taxes & fees
Feb 23 - Feb 24
3 bd 2 ba Unit
Interior entrance

Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner South Side
8.2 out of 10, Very Good, (272 reviews)
"The room was very clean and perfectly sized for a solo traveler for several nights."
United States
Valeri
Maverick Suites at 89 Marion
Classic Apartment, 3rd floor 3 Bedrooms | 1 bedroom, iron/ironing board, free cribs/infant beds, rollaway beds

Apartments in Salem

Apartments in Salem
3.0 star property
Salem
8.0 out of 10, Very Good, (48 reviews)
"The whole floor was clean and organized. The whole floor also felt inviting and comforting. We enjoyed how close we where to everthing. We were both so happy with found this apartment. "
United States
Jason
The price is ₩234,296
₩477,724 total
includes taxes & fees
Feb 23 - Feb 24
Apartments in Salem
Apartment (0 Bedroom) | Interior

1 Mi to Downtown Salem: Studio w/ Fire Pit Access

1 Mi to Downtown Salem: Studio w/ Fire Pit Access
3.0 star property
Salem
9.6 out of 10, Exceptional, (5 reviews)
"Studio was very nicely laid out and the owner of the property was friendly! Area the house was in was quiet but yet still walkable to downtown Salem. Bagel place across the street was amazing as well"
United States
chris
The price is ₩195,246
₩509,564 total
includes taxes & fees
Feb 27 - Feb 28
1 Mi to Downtown Salem: Studio w/ Fire Pit Access
House | 5 bedrooms, desk

Enchanting Hidden Door Escape

Enchanting Hidden Door Escape
2.0 star property
Stoneham
The price is ₩391,955
₩1,036,789 total
includes taxes & fees
Feb 22 - Feb 23
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 Winchester Hotel Reviews

The Dagny Boston

The Dagny Boston

10/10 Excellent
"The service was phenomenal. I’ve stayed at so many hotels/resorts this hotels service stood out to me. They went above & beyond to make us feel welcome & comfortable. The property location was perfect for walking downtown. The cafe wasn’t great despite the good reviews but everything else was 5/5 stars for me & my family. "
Jada 3-night trip
Posted 16 hours ago
The Dagny Boston

Find out more about Winchester

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Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we have vacation rentals in Winchester close to Winter Pond, or you can choose a more remote option if you're looking for a relaxing stay. Winchester is known for its soccer matches and lake views.

What can I see and do in Winchester?

While exploring the area, visit family-friendly sights like Winter Pond, or get outside and enjoy nature at Boston Common. Fenway Park and Encore Boston Harbor are other popular places to visit in the area.

What are vacation rentals like in Winchester?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Winchester. Vacation rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.