Holiday Rentals in Winchester

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Our top choices for Winchester holiday rentals

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 €202
includes taxes & fees
19 Feb - 20 Feb
Marriott Vacation Club® at Custom House, Boston

Furnished Apartment near BMC

Furnished Apartment near BMC
3.0 star property
South End
The price is €221
includes taxes & fees
18 Feb - 19 Feb
Furnished Apartment near BMC

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (658 reviews)
"Everything was great about this place! I will definitely be staying here again!"
United States
Amanda
Global Luxury Suites Downtown Boston

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 €295
includes taxes & fees
18 Feb - 19 Feb
The Chester Hotel

Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH

Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Beacon Hill
10.0 out of 10, Exceptional, (21 reviews)
"Great location, highly recommend it!"
United States
Aimee S.
The price is €667
includes taxes & fees
18 Feb - 19 Feb
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH

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 €140
includes taxes & fees
18 Feb - 19 Feb
Temple Place Suites

King Bed Loft in the Heart of Downtown Boston

King Bed Loft in the Heart of Downtown Boston
Downtown Boston
10.0 out of 10, Exceptional, (38 reviews)
"It was my first time staying here, and the room was very clean and fresh. The staff were extremely friendly and helpful, and the facilities were perfect. I will definitely stay here again, and I highly recommend it to anyone."
Japan
MINEKI
The price is €608
includes taxes & fees
18 Feb - 19 Feb
King Bed Loft in the Heart of Downtown Boston

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

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 €293
includes taxes & fees
18 Feb - 19 Feb
Charlesgate Suites

Luxury 1 bedroom downtown appartment

Luxury 1 bedroom downtown appartment
Government Center
10.0 out of 10, Exceptional, (5 reviews)
"This was absolutely phenomenal!! The apartment is immaculate, and the common areas are fabulous!! We used the outdoor deck and billiards table (on the 32nd floor, same floor the apartment is on.) Also, the "walk to all" location is great.Best of all, the unobstructed view is jaw dropping. Dina, the host, is delightful. Highly recommend this!!!"
United States
Paul G.
The price is €492
includes taxes & fees
12 Mar - 13 Mar
Luxury 1 bedroom downtown appartment

Bay Village Suites

Bay Village Suites
2.0 star property
Bay Village
6.6 out of 10, (253 reviews)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites

North End Entire House

North End Entire House
North End
10.0 out of 10, Exceptional, (16 reviews)
"Great location in the Northend!"
United States
Carol T.
The price is €440
includes taxes & fees
19 Feb - 20 Feb
North End Entire House

Best Location Studio In Downtown Boston

Best Location Studio In Downtown Boston
Downtown Boston
10.0 out of 10, Exceptional, (1 review)
"In town to celebrate a special event."
United States
Pam P.
The price is €245
includes taxes & fees
17 Mar - 18 Mar
Best Location Studio In Downtown Boston

Central Boston Beacon Hill 2brm

Central Boston Beacon Hill 2brm
Beacon Hill
9.2 out of 10, Wonderful, (21 reviews)
"Perfect location! Enjoyed our stay!"
United States
judith G.
The price is €371
includes taxes & fees
19 Mar - 20 Mar
Central Boston Beacon Hill 2brm

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

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 €176
includes taxes & fees
19 Feb - 20 Feb
Maverick Suites at 28 Fenway

Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston
2.5 star property
Everett
8.6 out of 10, Excellent, (11 reviews)
"The apartment was nice and very spacious. "
United States
Scott
Furnished Apartments near Encore Boston

Charming 2-bedroom apartment with WiFi, AC in superb Canton

Charming 2-bedroom apartment with WiFi, AC in superb Canton
Canton
9.8 out of 10, Exceptional, (18 reviews)
"Overall comfortable stay"
United States
Jolly J.
The price is €192
includes taxes & fees
19 Mar - 20 Mar
Charming 2-bedroom apartment with WiFi, AC in superb Canton

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,151 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

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 €595
includes taxes & fees
18 Feb - 19 Feb
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

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as €140 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 are some of the best holiday rentals that Winchester has to offer?

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino: This holiday home rental outside of Winchester is located on the waterfront, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

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. TD Garden and Fenway Park 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.