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

Holiday Rentals in Winchester

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Our top choices for Winchester holiday rentals

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (396 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 €155
includes taxes & fees
30 Jun - 1 Jul
Temple Place Suites

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 €273
includes taxes & fees
30 Jun - 1 Jul
The Chester Hotel

The Concord Hotel

The Concord Hotel
2.0 star property
South End
10.0 out of 10, Exceptional, (1 review)
"Overall had a great experience here. Took just a couple minutes texting the host to get the check in information that was to be emailed- but they sent it pretty quickly when I said it wasn't sent yet. I didn't need anything else from the host. It was clean and overall pretty nice! The stairs you take to get up to the room are pretty loud, so I woke up one time when other people got home to other rooms during my stay, but that was it! Overall good. I was there for a holiday weekend so the price...
United States
Jessica
The price is €291
includes taxes & fees
6 Jul - 7 Jul
The Concord Hotel

Central Salem Retreat 2bd W/ parking

Central Salem Retreat 2bd W/ parking
Salem
9.0 out of 10, Wonderful, (17 reviews)
"It was very clean, a great location, and the host was super responsive and helpful!"
United States
Kristen N.
The price is €256
includes taxes & fees
28 Jun - 29 Jun
Central Salem Retreat 2bd W/ parking

Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
10.0 out of 10, Exceptional, (3 reviews)
"It was a great stay!"
United States
Adina S.
The price is €220
includes taxes & fees
6 Jul - 7 Jul
Light-filled Studio | Back Bay

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (295 reviews)
"Great location and well maintained"
United States
EDDIE
The price is €145
includes taxes & fees
30 Jun - 1 Jul
Premier Suites - Bay Village

Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383
Quincy
9.8 out of 10, Exceptional, (52 reviews)
"The host was welcoming and answered all of my messages to her really fast. The house itself was beautiful, very clean, and close to everything."
United States
Deletra S.
The price is €456
includes taxes & fees
12 Jul - 13 Jul
Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

Modern 3BR Boston Nest • Pet-Friendly • Franklin Park & Red Line 558-2

Modern 3BR Boston Nest • Pet-Friendly • Franklin Park & Red Line 558-2
Dorchester
10.0 out of 10, Exceptional, (19 reviews)
"Very nice property, parking is safe, owner give clear checkin and checkout instructions. Very good."
United States
Kevin
The price is €427
includes taxes & fees
30 Jun - 1 Jul
Modern 3BR Boston Nest • Pet-Friendly • Franklin Park & Red Line 558-2

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 €206
includes taxes & fees
1 Jul - 2 Jul
Free Parking at 1 Bed Basement Apt, Near BU & MIT

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Marblehead Historic District
9.8 out of 10, Exceptional, (74 reviews)
"Great location, clean and comfortable, responsive host. Overall, a terrific stay. "
United States
Tiffany F.
The price is €236
includes taxes & fees
6 Jul - 7 Jul
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (84 reviews)
"Host was amazing and responded right away with any questions or concerns we had! Beautiful place to stay!"
United States
Amy I.
The price is €329
includes taxes & fees
14 Jul - 15 Jul
🎖The Boiler Room - Close to Subway & Downtown🎖

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)
"Interesting space with great kitchen setup, roomy, private, and reasonably convenient, and host was responsive immediately when there were problems at check-in (broken lock box and open front door upon arrival). However: the floor was very much not clean (as in, our socks were dirty after ten minutes inside without shoes), the thermostat did not work, and there is a pet door to an outside hallway that cannot be shut/locked. (There's also a lot of noise from the facility upstairs during the day,...
United States
Anastasia P.
The price is €202
includes taxes & fees
6 Jul - 7 Jul
Enjoyable 2-bedroom lower level apartment in charming Lynn

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, (14 reviews)
"Great property!!!"
United States
Heather
The price is €293
includes taxes & fees
30 Jun - 1 Jul
Hocus Pocus Season is here! Don’t miss it!

North End Studio

North End Studio
North End
9.4 out of 10, Exceptional, (60 reviews)
"Yes, kitchen was fully stocked with all dishes, glasses, cookware, and silverware. Even had paper products and all cleaning items. Place was very clean!!!"
United States
Kimberly
The price is €470
includes taxes & fees
8 Jul - 9 Jul
North End Studio

Cozy Studio Steps from Boston Common and Theaters

Cozy Studio Steps from Boston Common and Theaters
Bay Village
7.6 out of 10, Good, (14 reviews)
"Perfect location, terrible cleanliness."
United States
Cristina
The price is €300
includes taxes & fees
28 Jun - 29 Jun
Cozy Studio Steps from Boston Common and Theaters

Salem Haunted Happenings Retreat

Salem Haunted Happenings Retreat
Salem
9.8 out of 10, Exceptional, (27 reviews)
"Great place!"
United States
Jeffrey
The price is €217
includes taxes & fees
30 Jun - 1 Jul
Salem Haunted Happenings Retreat

2BR Historic Marblehead Home+Minutes to Beach

2BR Historic Marblehead Home+Minutes to Beach
Marblehead Historic District
10.0 out of 10, Exceptional, (25 reviews)
"Enjoyed our stay. "
United States
Mary D.
The price is €352
includes taxes & fees
1 Jul - 2 Jul
2BR Historic Marblehead Home+Minutes to Beach

Perfetto North End 1brm

Perfetto North End 1brm
North End
9.8 out of 10, Exceptional, (15 reviews)
"Great location- excellent place!"
United States
Deborah S.
Perfetto North End 1brm

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, (175 reviews)
"Room was clean and near the shops of Back Bay"
United States
Steven
The price is €163
includes taxes & fees
1 Jul - 2 Jul
Maverick Suites at 245 Newbury St

Bright 1 Bedroom | Downtown Boston

Bright 1 Bedroom | Downtown Boston
Bay Village
10.0 out of 10, Exceptional, (1 review)
"Great location to explore Boston with your dogs"
Canada
Thiery
The price is €285
includes taxes & fees
6 Jul - 7 Jul
Bright 1 Bedroom | Downtown Boston
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 €145 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?

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 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.