Winchester Town Hall and First Congregational Church at Winchester Center Historic District panorama in downtown Winchester, Massachusetts, USA.

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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, (635 reviews)
"Excellent location and clean room with beautiful views. Very comfortable and convenient."
United States
Noelle
The price is £279
includes taxes & fees
20 Jun - 21 Jun
Marriott Vacation Club® at Custom House, Boston

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (33 reviews)
"Charming room, fresh towels, clean!! I would stay here again."
United States
Mary
The price is £233
includes taxes & fees
30 Jun - 1 Jul
The Chester Hotel

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (707 reviews)
"Clean room, great staff and fantastic location for a reasonable price."
United States
April
The price is £212
includes taxes & fees
6 Jul - 7 Jul
Global Luxury Suites Downtown Boston

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (391 reviews)
"Wonderful stay at this property. Location was excellent, and the host is very quick and responsive to answer any questions you may have."
United States
Jennifer
The price is £152
includes taxes & fees
21 Jun - 22 Jun
Temple Place Suites

Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (288 reviews)
"Amazing location we loved it"
United States
MARLYN
The price is £326
includes taxes & fees
20 Jun - 21 Jun
Kasa Boston at Fenway

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
8.0 out of 10, Very good, (2 reviews)
"The property was great, aside from very busy outside streets, which made it difficult to sleep, but was not the fault of the host."
United States
Nicholas
The price is £243
includes taxes & fees
5 Jul - 6 Jul
Symple Live

Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.6 out of 10, Exceptional, (10 reviews)
The price is £185
includes taxes & fees
7 Jul - 8 Jul
Enjoyable 2-bedroom lower level apartment in charming Lynn

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (214 reviews)
The price is £286
includes taxes & fees
21 Jun - 22 Jun
Charlesgate Suites

The Concord Hotel

The Concord Hotel
2.0 star property
South End
The price is £249
includes taxes & fees
21 Jun - 22 Jun
The Concord Hotel

Awesome downtown location - walking distance to great restaurants, Boston Common, Southie + Seaport

Awesome downtown location - walking distance to great restaurants, Boston Common, Southie + Seaport
Downtown Boston
9.4 out of 10, Exceptional, (3 reviews)
"Location was awesome and central to the attractions. "
United States
Shelly B.
The price is £369
includes taxes & fees
2 Jul - 3 Jul
Awesome downtown location - walking distance to great restaurants, Boston Common, Southie + Seaport

Prime Central 1brm in North End Boston

Prime Central 1brm in North End Boston
North End
9.6 out of 10, Exceptional, (25 reviews)
"Excellent location, wonderful unit! "
United States
Mary M.
The price is £355
includes taxes & fees
22 Jun - 23 Jun
Prime Central 1brm in North End Boston

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (292 reviews)
"Great location and well maintained"
United States
EDDIE
The price is £143
includes taxes & fees
2 Jul - 3 Jul
Premier Suites - Bay Village

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (375 reviews)
"Great stay. "
United States
Anna
The price is £184
includes taxes & fees
21 Jun - 22 Jun
Maverick Suites at 28 Fenway

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (156 reviews)
"The property is clean and for the money, is a win for the visitor. "
United States
Ramon S
The price is £109
includes taxes & fees
12 Jul - 13 Jul
Maverick Suites at 400 Columbus Ave

Free Parking at 1 Bed Basement Apt, Near BU & MIT

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.4 out of 10, Very good, (23 reviews)
"Friendly hosts"
United States
Jan
The price is £246
includes taxes & fees
30 Jun - 1 Jul
Free Parking at 1 Bed Basement Apt, Near BU & MIT

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (121 reviews)
"This was. A very nice, clean room. Plenty big enough for one or two people and great location, lots of dining and by the park"
United States
Rachel
The price is £151
includes taxes & fees
21 Jun - 22 Jun
Maverick Suites at 40 Temple St

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, (174 reviews)
"Room was clean and near the shops of Back Bay"
United States
Steven
The price is £166
includes taxes & fees
24 Jun - 25 Jun
Maverick Suites at 245 Newbury St

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.8 out of 10, Excellent, (11 reviews)
"Excellent location for restaurants, shops, sightseeing. Lovely buzz around the area, with park & river close by to escape if necessary. Large lounge area to put your feet up between trips, and adequate glasses etc for drinks and nibbles between the treats at the bakeries and restaurants nearby."
United Kingdom
Jude
The price is £316
includes taxes & fees
1 Jul - 2 Jul
Stylish Back Bay Retreat, Steps from Prudential

Cozy Modern 2 Bedrooms Apartment Close to Boston

Cozy Modern 2 Bedrooms Apartment Close to Boston
Revere
10.0 out of 10, Exceptional, (50 reviews)
"It was a very enjoyable stay. Was very close to many attractions and everything was well kept. "
United States
Naomi S.
The price is £331
includes taxes & fees
22 Jun - 23 Jun
Cozy Modern 2 Bedrooms Apartment Close to Boston

Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (33 reviews)
"Great place in a great location!! Very clean perfect! "
United States
Jaylen D.
The price is £257
includes taxes & fees
30 Jun - 1 Jul
Bright 2BR by Boston Waterfront
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 £109 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. 

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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?

Boston's Best Vacation Home : This holiday home rental outside of Winchester is equipped with a fireplace, air conditioning and laundry facilities to help you feel comfortable during your stay.

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 Harbor. 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.