Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (325)
"Good place"
United States
Elijah
The price is NZ$344
includes taxes & fees
13 Jan - 14 Jan 2026
Maverick Suites at 28 Fenway

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (325)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is NZ$287
includes taxes & fees
14 Dec - 15 Dec
Temple Place Suites

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (630)
"This unit and location was perfect for my trip! Super close to many of the attractions that we wanted to visit. "
United States
Lily
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, (154)
"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 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner South Side
8.2 out of 10, Very good, (270)
"Had an amazing time. Loved the property and it's location in proximity to entertainment, transportation, dining and scenic entertainment. "
United States
Nicole
Maverick Suites at 89 Marion

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (251)
"Clean room, good location, check in check out easily!"
United States
HIEN T
Premier Suites - Bay Village

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1143)
"Lovely, quiet place."
United States
Fatu
Crescent Suites Hotel

Bay Village Suites

Bay Village Suites
2.0 star property
Bay Village
6.4 out of 10, (250)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites

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

The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (28)
"Amazing property, would stay again."
United States
Doug
The price is NZ$1,407
includes taxes & fees
16 Dec - 17 Dec
The Monty Boston

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (133)
"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

Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
7.8 out of 10, Good, (68)
"Loved how cozy and clean it was. Location was great, near many points of interest. Parking at an extra fee, but plenty of street parking in the area. "
United States
Isaiah Joel Santa
Maverick Suites at 402 Columbus Ave

Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (176)
"The place was very nice and nicely equipped, but a little difficult to locate."
United States
William
The price is NZ$354
includes taxes & fees
29 Dec - 30 Dec
Global Luxury Suites East 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 NZ$637
includes taxes & fees
15 Dec - 16 Dec
Charlesgate Suites

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (28)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
The price is NZ$603
includes taxes & fees
21 Dec - 22 Dec
The Chester Hotel

Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett
3.0 star property
Everett
10.0 out of 10, Exceptional, (1)
"Honestly this was one of the best furnished apartments I’ve ever stayed in, and I travel a lot for work. My partner and I came with another couple and we all kept saying how we wished we had booked a few extra nights. The place was super clean, modern, and honestly way bigger than we expected lol. First night we accidentally got the wrong door code but the host fixed it in like two minutes which was amazing. The living room became our hangout spot every evening and we even cooked dinner together...
United States
Yitzy
Luxury Apartments by Hyatus at Boston Everett

The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!

The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!
Downtown Salem
9.6 out of 10, Exceptional, (61)
"Amazing place to stay! Love the attention to decorating details, from the spooky lighting to the Alexa “Scroll of Spells” and it’s within close walking distance to many Salem attractions! Would recommend to anyone!"
United States
More M.
The price is NZ$1,294
includes taxes & fees
15 Dec - 16 Dec
The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
South Boston
9.8 out of 10, Exceptional, (182)
"Great home with everything you need for an awesome stay. "
United States
Lisa B.
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

Modern 2 BR, 1BA Near Convention Center & Seaport

Modern 2 BR, 1BA Near Convention Center & Seaport
South Boston
9.8 out of 10, Exceptional, (201)
"The apartment and location were excellent. We loved how convenient it was to access all the attractions."
United States
Monica B.
Modern 2 BR, 1BA Near Convention Center & Seaport

Apartments in Salem

Apartments in Salem
3.0 star property
Salem
8.0 out of 10, Very good, (48)
"Property was fine. It is well located to see the sites in Salem. Only negative was that the neighbors were a bit loud at night. "
United States
Wes
Apartments in Salem
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, 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 NZ$287 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. Fenway Park and Harvard Square 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.