Holiday Rentals in Winchester

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Our top choices for Winchester holiday rentals

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.4 out of 10, Very good, (30 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is €307
includes taxes & fees
19 May - 20 May
The Chester Hotel

Blissful South End Studio

Blissful South End Studio
Back Bay
9.4 out of 10, Exceptional, (3 reviews)
"Great place on a quiet street convenient to everything!"
United States
Penelope D.
The price is €218
includes taxes & fees
18 May - 19 May
Blissful South End Studio

Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!
Downtown Boston
8.6 out of 10, Excellent, (18 reviews)
"Came to Boston to take a few college tours and this was a pretty central location. This property was also very close to several other places we were hoping to see while in town. Communication was great and check in was seamless. The property was clean and perfect for our stay. "
United States
elena d.
The price is €249
includes taxes & fees
19 May - 20 May
Perfect One Bedroom Stay In Downtown Boston!

2BR Historic Marblehead Home+Minutes to Beach

2BR Historic Marblehead Home+Minutes to Beach
Marblehead Historic District
10.0 out of 10, Exceptional, (20 reviews)
"Location and amenities were great! Close to everything , yet private. Comfortable and clean . Host was most helpful.Will definitely try to stay again when traveling to the area ."
United States
George G.
The price is €314
includes taxes & fees
13 May - 14 May
2BR Historic Marblehead Home+Minutes to Beach

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

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.0 out of 10, Very good, (14 reviews)
"Great location, check in and check out was easy. Clean space. Great value "
United States
David
The price is €284
includes taxes & fees
24 May - 25 May
Free Parking at 1 Bed Basement Apt, Near BU & MIT

3BR3Bth Entire House/Steps to Downtown & TD Garden

3BR3Bth Entire House/Steps to Downtown & TD Garden
North End
10.0 out of 10, Exceptional, (10 reviews)
"This place is so cool! Was incredibly clean, updated and offered all the amenities you need for a weekend get away. The location is wonderful as well with lots of markets, bakeries and restaurants all within walking distance. This is a must stay! "
United States
mary j.
3BR3Bth Entire House/Steps to Downtown & TD Garden

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (113 reviews)
"A phenomenal stay at maverick suites! The location was fantastic, the room was spotless and cozy, and the check-in/out process was a breeze. I’d happily stay here again and recommend to anyone taking a trip to Boston!"
United States
Kendra
The price is €302
includes taxes & fees
19 May - 20 May
Maverick Suites at 40 Temple St

Ideal North End 1brm Central To Everything

Ideal North End 1brm Central To Everything
North End
9.6 out of 10, Exceptional, (41 reviews)
"Great well appointed place, close to everything Boston has to offer."
United States
Robert M.
The price is €432
includes taxes & fees
22 May - 23 May
Ideal North End 1brm Central To Everything

Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
9.2 out of 10, Wonderful, (5 reviews)
"Would stay again"
United States
mark p.
The price is €253
includes taxes & fees
31 May - 1 Jun
Studio Awaits Your Next Stay!

Primo North End Studio

Primo North End Studio
North End
9.2 out of 10, Wonderful, (14 reviews)
"Great place, amazing location!"
United States
Christopher W.
The price is €359
includes taxes & fees
3 Jun - 4 Jun
Primo North End Studio

Cozy Studio Steps from Boston Common and Theaters

Cozy Studio Steps from Boston Common and Theaters
Bay Village
8.0 out of 10, Very good, (12 reviews)
"Was clean and the location was perfect for my stay. "
United States
Laurie F.
The price is €321
includes taxes & fees
17 May - 18 May
Cozy Studio Steps from Boston Common and Theaters

Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.4 out of 10, Exceptional, (6 reviews)
The price is €214
includes taxes & fees
25 May - 26 May
Enjoyable 2-bedroom lower level apartment in charming Lynn

Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking

Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking
Beverly
9.2 out of 10, Wonderful, (24 reviews)
"Cheerful decor, well-equipped kitchen, and clean. Good location in walking distance to restaurants. However, there was a musty smell throughout the building and rooms. "
United States
Julia
The price is €261
includes taxes & fees
13 May - 14 May
Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking

Hocus Pocus Season is here! Don’t miss it!

Hocus Pocus Season is here! Don’t miss it!
Salem
10.0 out of 10, Exceptional, (10 reviews)
"Great property!!!"
United States
Heather
The price is €260
includes taxes & fees
13 May - 14 May
Hocus Pocus Season is here! Don’t miss it!

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
8.0 out of 10, Very good, (41 reviews)
"Very convenient for our stay with a grandson attending Harvard"
United States
Christy
The price is €283
includes taxes & fees
31 May - 1 Jun
On River/Harvard Sq. two blocks

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, (167 reviews)
"Great place for a solo business trip. Great location"
United States
Eleazar
The price is €288
includes taxes & fees
20 May - 21 May
Maverick Suites at 245 Newbury St

Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.

Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
Medford
10.0 out of 10, Exceptional, (56 reviews)
"Owner accessible, and cleanliness and convenience was very good."
United States
Ian
The price is €222
includes taxes & fees
13 May - 14 May
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.

Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
10.0 out of 10, Exceptional, (26 reviews)
"Great property to stay with proximity to everything you need, and a safe neighborhood to walk all times of the day. The hosts were very communicative and quick to respond to any questions I had. The apartment itself was spacious and had a nice kitchen to prepare meals. I would recommend to all considering a stay in East Boston!"
United States
Jordan
The price is €305
includes taxes & fees
1 Jun - 2 Jun
Bright 2BR by Boston Waterfront

Salem Haunted Happenings Retreat

Salem Haunted Happenings Retreat
Salem
9.8 out of 10, Exceptional, (25 reviews)
"Great place!"
United States
Jeffrey
The price is €212
includes taxes & fees
26 May - 27 May
Salem Haunted Happenings Retreat

Bee-Themed Stay Near Boston – A Sweet and Unique Getaway

Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
Billerica
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful place that made our vacation even better. There were so many hidden gems and the amenities were abundant. "
United States
Elizabeth
Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
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 €136 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?

Centrally located in the heart of Boston near T: This holiday home rental outside of Winchester has air conditioning and laundry facilities to help you feel perfectly comfortable 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.

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.