Winchester Vacation Rentals from NT$2,958: Search Short-Term Rentals

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Vacation Rentals in Winchester

Enjoy a comfortable stay in this well-appointed room with a neatly made bed, desk, and seating area.

"Near Boston Commons was very nice"

NT$5,597 total

includes taxes & fees

Jul 13 - Jul 14

Cozy retreat with a large bed, fireplace, and large windows.

"The room was decent but the bathroom was very small. The only big inconvenience was finding somewhere to park. "

NT$3,400 total

includes taxes & fees

Jul 21 - Jul 22

Relax in our spacious lobby, featuring a central seating area with sofas and a coffee table, and a large glass door leading to the exterior.

"Very clean, safe, and convenient. Beautiful accommodations."

Experience modern comfort in this stylish room, featuring a large bed, sleek bar stools, and a touch of greenery.

"If you need a place to sleep close to Fenway this is the perfect place."

NT$7,902 total

includes taxes & fees

Jul 28 - Jul 29

1 bedroom, desk, laptop workspace, free WiFi

"Easy check-in, clean. "

Relax in a serene outdoor seating area surrounded by lush foliage and a vibrant bush with yellow flowers.

"Stayed for 2 nights. Quiet hotel, walking distance to restaurants and bars. Loved our stay!"

Enjoy expansive views from the large windows in this open layout room, featuring a circular seating area and contemporary furniture.

"We really enjoyed our stay. It was an apartment feel in a great area of Cambridge "

NT$7,407 total

includes taxes & fees

Aug 9 - Aug 10

Relax and socialize on the outdoor terrace with a fire pit, seating area, and stunning city views.

"Great location, clean room and had everything we needed "

NT$8,179 total

includes taxes & fees

Jul 27 - Jul 28

Traditional townhouses with bay windows and ornate detailing line the street, offering a mix of residential and commercial spaces.

"We had no issues, felt at home, enjoyed the quiet, unit perfect for two "

NT$10,848 total

includes taxes & fees

Aug 11 - Aug 12

Enjoy a panoramic city view from the large windows in this spacious room with a high ceiling.

"Great apartment in a super convenient location near Fenway and BU. Easy access, clean, great views. Definitely would stay here again!"

NT$9,205 total

includes taxes & fees

Jul 29 - Jul 30

Stunning entrance with a grand staircase and elegant door, flanked by wooden panels and a glass window.

"Well kept old building with nice features "

NT$9,139 total

includes taxes & fees

Aug 11 - Aug 12

Relax in this stylish corner room with a city view, featuring a comfortable reading nook with a small table and stool.

"Property is located in a very nice area. No frill, what they advertise, you get. "

NT$8,037 total

includes taxes & fees

Aug 11 - Aug 12

Relax and take in the breathtaking city skyline and water views from our rooftop lounge, featuring comfortable seating and shaded areas.

"Amazing location right by the water, quiet building and clean. But the furniture is really uncomfortable, particularly the couch which is the only seating, it’s a pull out bed so the entire sofa sinks in low. The bed isn’t solid and easily slides off the frame just by sitting on it. We also had a delivery order stolen from the front desk area. "

NT$10,386 total

includes taxes & fees

Jul 27 - Jul 28

Enter a charming brick building with a black-framed entrance door and a beautiful potted plant.

"Great place , size of the apartment , very clean"

NT$8,494 total

includes taxes & fees

Aug 10 - Aug 11

Rows of charming townhouses with large windows and fire escapes line the cobblestone street.

"Very cozy and centrally located. Satellite tv didn’t work. "

NT$11,180 total

includes taxes & fees

Aug 12 - Aug 13

Relax in a spacious living area with a large L-shaped sofa, dining table, and bookshelf.

"Apt very well located , close to historical areas , good restaurants Very spacious"

NT$22,208 total

includes taxes & fees

Jul 13 - Jul 14

Enjoy cooking in this well-equipped kitchen with a central island and appliances.

"Location was perfect. Walking distance to so many things!! The kitchen could have been a little bit better stocked. No coffee or salt and pepper. "

NT$8,006 total

includes taxes & fees

Aug 11 - Aug 12

Relax in a classic hotel room with a large bed, upholstered bench, and city view.

"Excellent property, well appointed, clean and with all the essentials for a comfortable stay. Close to public transportation and several restaurants and eateries nearby. Easy check in and out. The only negative is the city noise: sirens, traffic, etc. but that comes with the convenience of being in the city."

NT$13,366 total

includes taxes & fees

Jul 13 - Jul 14

Experience a comfortable stay in this elegantly designed room with a large bed, bedside tables, and a television.

"Awesome property, conveniently located near everything, especially Fenway. Definitely will stay here again. "

NT$13,681 total

includes taxes & fees

Jul 29 - Jul 30

Enjoy a comfortable stay in this stylish apartment with a sleek kitchen, cozy living area, and dining space.

NT$7,610 total

includes taxes & fees

Jul 13 - Jul 14

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Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Recent reviews of Winchester properties

5/5 Excellent

"It was a great location to walk or hop on the subway to get anywhere we wanted to go. The hotel was very nice and the staff was great!"

A verified traveler stayed at The Dagny Boston

Posted 6 hours ago

5/5 Excellent

"this property was perfect for our stay in Bostain. First of all the room was large, clean and very comfortable. The front desk staff was very pleasant. The best part about this hotel is the location. You are on the waterfront and within walking distance of everything you need including many tours. We were there for five days and never even moved our car. I would definitely recommend this hotel to anyone planning a trip to Boston. "

A verified traveler stayed at Harborside Inn Of Boston

Posted 1 day ago

5/5 Excellent

"We had a great time here! The rooms were nice and very clean, and every staff member we ran into was friendly and helpful. The location is great, which is a nice bonus. Parks, shopping, and dining are all within walking distance. I'll definitely stay here again next time I'm in Boston. "

A verified traveler stayed at The Godfrey Hotel Boston

Posted 1 day ago

5/5 Excellent

"Very fabulous hotel, combination of Scandinavian functionality and aesthetics. Everything in the room (tiny, but not as tiny as a Japanese hotel room) is so well-thought out. The iPad controls everything in the room: lights, curtains, TV, temperature etc. The night curtain truly blacks out the room. The mattress is not saggy - super comfortable. The light in the bathroom changes colour on command; there’s also a memory game to play (“Marvin” changes the colour of the light and you have to repeat). Breakfast alternates between two options. Free flat, sparkling and hot water at the bar 24/7. My only issue is the smell of sewage from bathroom. Not overpowering but noticeable. Overall, a delightful stay! Thanks citizenM!"

A verified traveler stayed at citizenM Boston Back Bay

Posted 2 days ago

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we have vacation rentals in Winchester close to Winter Pond, or you can choose a more remote option if you're looking for a relaxing stay. Winchester is known for its soccer matches and lake views.

What can I see and do in Winchester?

Family-friendly attractions include Winter Pond, whereas Middlesex Fells Reservation is a spot to enjoy the outdoors. TD Garden and Fenway Park are other popular places to visit in the area.

What are vacation rentals like in Winchester?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Winchester. Vacation rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.

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Winchester Vacation Rentals

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Vacation Rentals in Winchester

Temple Place Suites

Premier Suites - Bay Village

Global Luxury Suites Downtown Boston

Maverick Suites at 28 Fenway

Bay Village Suites

Crescent Suites Hotel

907 Main Hotel Central Square, Sonder by Marriott Bonvoy

No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy

Maverick Suites at 245 Newbury St

Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway

Maverick Suites at 89 Marion

Maverick Suites at 400 Columbus Ave

Global Luxury Suites East Boston

Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay

Maverick Suites at 40 Temple St

The Monty Boston

Maverick Suites at 402 Columbus Ave

The Chester Hotel

Charlesgate Suites

Furnished Apartments near Encore Boston

Find out more about Winchester

Recent reviews of Winchester properties

The Dagny Boston

The Westin Boston Seaport District

Hilton Boston Park Plaza

Hilton Boston Logan Airport

Harborside Inn Of Boston

The Godfrey Hotel Boston

The Arcadian Hotel

Hyatt Regency Boston/Cambridge

citizenM Boston Back Bay

Frequently asked questions