Holiday Rentals in Winchester

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Our top choices for Winchester holiday rentals

Bay Village Suites

Bay Village Suites
2.0 star property
Bay Village
6.6 out of 10, (252)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (328)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is €142
includes taxes & fees
7 Jan - 8 Jan
Temple Place Suites

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.2 out of 10, Good, (134)
"Good location, compact room with everything you need. Very convenient self-service token-operated washing machine and dryer. Worth the price. No elevators, and bed is a bit small."
United Kingdom
Fanny Pei Yee
Maverick Suites at 400 Columbus Ave

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (638)
"Very clean, beautiful place. I would stay there again."
Canada
Liam
Global Luxury Suites Downtown Boston

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, (155)
"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

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (102)
"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

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (255)
"Clean room, good location, check in check out easily!"
United States
HIEN T
Premier Suites - Bay Village

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (28)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
United States
kelly
The price is €298
includes taxes & fees
6 Jan - 7 Jan
The Chester Hotel

The Chester: Hip, Renovated, South End

The Chester: Hip, Renovated, South End
2.0 star property
South End
10.0 out of 10, Exceptional, (2)
"Nice room. Good location "
United States
Abenamar A.
The price is €302
includes taxes & fees
5 Jan - 6 Jan
The Chester: Hip, Renovated, South End

Best Location Studio In Downtown Boston

Best Location Studio In Downtown Boston
Downtown Boston
10.0 out of 10, Exceptional, (1)
"In town to celebrate a special event."
United States
Pam P.
The price is €195
includes taxes & fees
11 Jan - 12 Jan
Best Location Studio In Downtown Boston

Walk to Boston Common, Safe & Central Stay

Walk to Boston Common, Safe & Central Stay
Beacon Hill
7.2 out of 10, Good, (17)
"Property was excellent. Transportation was easy and communication with host was great. Thanks for a great vacation in beautiful Boston."
United States
john
The price is €250
includes taxes & fees
8 Jan - 9 Jan
Walk to Boston Common, Safe & Central Stay

Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
9.2 out of 10, Wonderful, (5)
"Would stay again"
United States
mark p.
The price is €197
includes taxes & fees
3 Jan - 4 Jan
Studio Awaits Your Next Stay!

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (332)
"Good place"
United States
Elijah
The price is €176
includes taxes & fees
29 Jan - 30 Jan
Maverick Suites at 28 Fenway

North End Gem ★ Prime Location + Parking Included

North End Gem ★ Prime Location + Parking Included
North End
9.6 out of 10, Exceptional, (59)
"Had a very nice time close to everything walking distance to alot of fun and exciting things "
United States
Lynn W.
The price is €304
includes taxes & fees
3 Jan - 4 Jan
North End Gem ★ Prime Location + Parking Included

Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!
Downtown Boston
8.6 out of 10, Excellent, (18)
"Temple Place Suites was a great place to stay for our few days in Boston. We loved being across from Boston Commons, near great bakerys and cafes. It was a comfortable apartment with great space and plenty of amenities. Staff was great at communicating about check in, building codes and check out. Wished there were dish towels and wash cloths. Otherwise, it was great!!"
United States
Christine
The price is €200
includes taxes & fees
3 Jan - 4 Jan
Perfect One Bedroom Stay In Downtown Boston!

Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston
2.5 star property
Everett
8.6 out of 10, Excellent, (9)
"Great place. Very clean. Great communication."
United States
Michele
The price is €218
includes taxes & fees
3 Jan - 4 Jan
Furnished Apartments near Encore Boston

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (201)
"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
3 Jan - 4 Jan
Charlesgate Suites

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.6 out of 10, Excellent, (7)
"Beautiful place right on historic Newbury Street. I’ll definitely return and I’d highly recommend this apartment."
United States
JEANPAUL
The price is €256
includes taxes & fees
3 Jan - 4 Jan
Stylish Back Bay Retreat, Steps from Prudential

Come Visit Boston and Stay In Our Homey Studio

Come Visit Boston and Stay In Our Homey Studio
Downtown Boston
8.8 out of 10, Excellent, (3)
"Great central location! Tiny but super !would come back . Great food , bars, brewery , breakfast at our doorstep. By the park too!"
United States
Dean and Courtenay M.
The price is €200
includes taxes & fees
7 Jan - 8 Jan
Come Visit Boston and Stay In Our Homey Studio

Gorgeous Beacon Hills Studio next to State house

Gorgeous Beacon Hills Studio next to State house
Beacon Hill
9.8 out of 10, Exceptional, (32)
"Loved the private outdoor patio"
United States
Robin P.
The price is €305
includes taxes & fees
4 Jan - 5 Jan
Gorgeous Beacon Hills Studio next to State 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

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 €142 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?

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi: This holiday home rental outside of Winchester is located in the city centre, and offers a balcony, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.