Winchester Holiday Rentals

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Holiday Rentals in Winchester

Temple Place Suites
2.5 star property
7.0 out of 10, Good, (298)
"Very convenient place to stay, near transportation and waking distance to historic points and shopping. "
United States
Carolina
The price is AU$265
includes taxes & fees
16 Nov - 17 Nov
Temple Place Suites
Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (1114)
"The staff were friendly and the accommodation was good"
United States
Sudha
Crescent Suites Hotel
Premier Suites - Bay Village
2.0 star property
6.4 out of 10, (237)
"Clean room, good location, check in check out easily!"
United States
HIEN T
The price is AU$429
includes taxes & fees
26 Oct - 27 Oct
Premier Suites - Bay Village
907 Main Hotel Central Square, Sonder by Marriott Bonvoy
4.0 star property
8.2 out of 10, Very good, (531)
"Friendly service, great location and design. "
United States
Johannes
The price is AU$239
includes taxes & fees
23 Nov - 24 Nov
907 Main Hotel Central Square, Sonder by Marriott Bonvoy
Bay Village Suites
2.0 star property
6.4 out of 10, (235)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites
Maverick Suites at 28 Fenway
3.0 star property
8.8 out of 10, Excellent, (303)
"great location"
United States
Mario
The price is AU$321
includes taxes & fees
18 Nov - 19 Nov
Maverick Suites at 28 Fenway
Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very good, (614)
"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 89 Marion
2.0 star property
8.4 out of 10, Very good, (261)
"Had an amazing time. Loved the property and it's location in proximity to entertainment, transportation, dining and scenic entertainment. "
United States
Nicole
The price is AU$332
includes taxes & fees
23 Nov - 24 Nov
Maverick Suites at 89 Marion
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
4.0 star property
9.2 out of 10, Wonderful, (944)
"The property was awesome, well located, not far to jump on trains etc Close to MGM musical hall, which was the reason for our trip. Would 100% recommend this property if your looking for a nice peaceful area but close enough to all the popular touristy areas. Loved our stay, thank you "
United Kingdom
Lyndsey
The price is AU$308
includes taxes & fees
9 Nov - 10 Nov
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
The Chester Hotel
4.0 star property
8.4 out of 10, Very good, (25)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
The price is AU$588
includes taxes & fees
26 Oct - 27 Oct
The Chester Hotel
Maverick Suites at 400 Columbus Ave
2.0 star property
7.2 out of 10, Good, (126)
"I thoroughly enjoyed my stay. Great property in a nice neighborhood in Back Bay. Bonus: it's also near the Logan Express bus stop for easy airport access. "
United States
Mark
The price is AU$303
includes taxes & fees
18 Nov - 19 Nov
Maverick Suites at 400 Columbus Ave
Global Luxury Suites East Boston
4.0 star property
6.8 out of 10, (169)
"I will not be staying there again. "
United States
Malcolm
The price is AU$378
includes taxes & fees
23 Nov - 24 Nov
Global Luxury Suites East Boston
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
4.0 star property
8.8 out of 10, Excellent, (273)
"Easy check in and clean property with in unit laundry"
United States
Sarah
The price is AU$341
includes taxes & fees
9 Nov - 10 Nov
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
3.5 star property
8.8 out of 10, Excellent, (77)
"Excellent location in the heart of shops. Quiet and clean location. Highly recommend and would definitely stay again ❤️."
United States
Michelle
The price is AU$466
includes taxes & fees
13 Nov - 14 Nov
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
Maverick Suites at 245 Newbury St
2.0 star property
8.2 out of 10, Very good, (150)
"Clean. Bed super comfortable, easy walk to Fenway, restaurants, subway, shops, library"
United States
Elizabeth rising
The price is AU$392
includes taxes & fees
18 Nov - 19 Nov
Maverick Suites at 245 Newbury St
Maverick Suites at 40 Temple St
2.0 star property
7.4 out of 10, Good, (99)
"Great location "
Canada
James
The price is AU$375
includes taxes & fees
18 Nov - 19 Nov
Maverick Suites at 40 Temple St
Maverick Suites at 402 Columbus Ave
2.5 star property
8.0 out of 10, Very good, (65)
"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
The price is AU$327
includes taxes & fees
23 Nov - 24 Nov
Maverick Suites at 402 Columbus Ave
Charlesgate Suites
3.5 star property
9.4 out of 10, Exceptional, (194)
"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 AU$632
includes taxes & fees
10 Nov - 11 Nov
Charlesgate Suites
The Monty Boston
2.5 star property
9.4 out of 10, Exceptional, (25)
"Thos was agreat place to stay for my family. It is very spacious."
United States
David
The price is AU$1,343
includes taxes & fees
31 Oct - 1 Nov
The Monty Boston
Furnished Apartments near Encore Boston
2.5 star property
8.4 out of 10, Very good, (6)
"Great place. Very clean. Great communication."
United States
Michele
The price is AU$595
includes taxes & fees
26 Oct - 27 Oct
Furnished Apartments near Encore 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, 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 favourite 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 depend 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 AU$239 per night. Entering your travel dates in the search wizard might find you 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?

Casa Castor • Private Room 1: This holiday home rental outside of Winchester has air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge to make your meal-planning easier.

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.