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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Winchester holiday rentals

Desk, laptop workspace, free WiFi, bed sheets

Aparthotel in Bay Village

Bay Village Suites
2.0 star property
6.6 out of 10, (254 reviews)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites
Lobby lounge

Aparthotel in Chinatown

Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very good, (665 reviews)
"Everything was great about this place! I will definitely be staying here again!"
United States
Amanda
Global Luxury Suites Downtown Boston
Exterior

Aparthotel in Back Bay

Maverick Suites at 245 Newbury St
2.0 star property
8.2 out of 10, Very good, (159 reviews)
"Great location, clean and great 😌 "
United States
Catherine
Maverick Suites at 245 Newbury St
Rooftop terrace

Condo resort in Downtown Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
9.4 out of 10, Exceptional, (620 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 5.761.546 ₫
6.622.897 ₫ total
includes taxes & fees
22 Mar - 23 Mar
Marriott Vacation Club® at Custom House, Boston
42-inch TV with satellite channels

Aparthotel in South End

Maverick Suites at 400 Columbus Ave
2.0 star property
7.4 out of 10, Good, (136 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
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets

Apartment in Downtown Boston

Temple Place Suites
2.5 star property
7.2 out of 10, Good, (334 reviews)
"The location is fantastic, the bed is really comfortable. I will stay there again."
Canada
Ivan
The price is 2.345.220 ₫
4.343.283 ₫ total
includes taxes & fees
5 Mar - 6 Mar
Temple Place Suites
Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets

Aparthotel in Bay Village

Premier Suites - Bay Village
2.0 star property
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
The price is 3.335.424 ₫
5.181.985 ₫ total
includes taxes & fees
20 Mar - 21 Mar
Premier Suites - Bay Village
Front of property

Aparthotel in Beacon Hill

Maverick Suites at 40 Temple St
2.0 star property
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
Front of property

Apartment in Fenway–Kenmore

Maverick Suites at 28 Fenway
3.0 star property
8.6 out of 10, Excellent, (337 reviews)
"Good place"
United States
Elijah
The price is 2.462.481 ₫
5.376.683 ₫ total
includes taxes & fees
5 Mar - 6 Mar
Maverick Suites at 28 Fenway
Premium Apartment | Living area | 24-inch Smart TV with digital channels

Aparthotel in South End

The Chester Hotel
4.0 star property
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 4.573.179 ₫
9.899.686 ₫ total
includes taxes & fees
4 Mar - 5 Mar
The Chester Hotel
Terrace/patio

Aparthotel in South Side

Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (1,152 reviews)
"Everything about this facility was pleasing: clean, well-appointed, great kitchen, comfortable, well-located in the area. We were given a warm welcome when we arrived, provided with lots of information about Waltham. Located near shops and restaurants and on a walking trail along the Charles River. Highly recommend and would stay here again. "
Canada
Susan
Crescent Suites Hotel
Family Apartment | Living area

Apartment in East Somerville

3 bd 2 ba Unit
3.0 star property
The price is 9.308.178 ₫
14.305.934 ₫ total
includes taxes & fees
7 Mar - 8 Mar
3 bd 2 ba Unit
Interior entrance

Aparthotel in Coolidge Corner South Side

Maverick Suites at 89 Marion
2.0 star property
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
Premium Studio Suite | Premium bedding, desk, iron/ironing board, free WiFi

Aparthotel in Fenway–Kenmore

Charlesgate Suites
3.5 star property
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 4.501.412 ₫
9.686.934 ₫ total
includes taxes & fees
4 Mar - 5 Mar
Charlesgate Suites
Outdoor dining

Condo in Marblehead Historic District

Zen vacation in historic Marblehead
3.0 star property
The price is 7.687.110 ₫
11.843.753 ₫ total
includes taxes & fees
8 Mar - 9 Mar
Zen vacation in historic Marblehead
House | 5 bedrooms, desk

Holiday Home in Stoneham

Enchanting Hidden Door Escape
2.0 star property
The price is 7.326.835 ₫
19.219.343 ₫ total
includes taxes & fees
4 Mar - 5 Mar
Enchanting Hidden Door Escape
Apartment (1 Bedroom) | Interior

Apartment in Salem

1 Mi to Downtown: Salem Vacation Rental!
3.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Great overall stay! "
United States
Tessa
The price is 3.022.728 ₫
9.518.466 ₫ total
includes taxes & fees
8 Mar - 9 Mar
1 Mi to Downtown: Salem Vacation Rental!
Exterior

Aparthotel in South End

Maverick Suites at 402 Columbus Ave
2.5 star property
8.0 out of 10, Very good, (69 reviews)
"Loved how cozy and clean it was. Location was great, near many points of interest. Parking at an extra fee, but plenty of street parking in the area. "
United States
Isaiah Joel Santa
Maverick Suites at 402 Columbus Ave
Condo (The Warlock House) | Exterior

Condo in Salem

The Warlock House
3.0 star property
The price is 11.603.106 ₫
22.028.016 ₫ total
includes taxes & fees
5 Mar - 6 Mar
The Warlock House
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 Revolution Hotel

The Revolution Hotel

10/10 Excellent
"Best stay "
Mariama 4-night trip
Posted 21 hours ago
The Revolution Hotel

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Winter Pond, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its football 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 holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips.