Winchester Vacation Rentals

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Vacation Rentals in Winchester

Lobby lounge
Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very Good, (409)
"Decent place"
The price is ₩258,944
per night
May 27 - May 28
Global Luxury Suites Downtown Boston
Courtyard
HYATT house Boston/Burlington
3.0 star property
9.2 out of 10, Wonderful, (2203)
"Very clean and comfortable "
The price is ₩216,297
per night
May 27 - May 28
HYATT house Boston/Burlington
Deluxe Studio Suite | Living area
28 Fenway
2.0 star property
9.6 out of 10, Exceptional, (48)
"Cozy accommodations close to Back Bay and Fenway. A little too cozy for a couple - better for a solo leisure stay (no desk or working space). Rooms in pics look bigger than what it actually is. Garden level rooms will be a bit noisy. Excellent location and spotless and good security. "
28 Fenway
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Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets
Temple Place Suites
2.5 star property
6.8 out of 10, (81)
"Property was excellent, right outside were too many bums I had to walk by in order to get there"
The price is ₩187,730
per night
Jun 9 - Jun 10
Temple Place Suites
Desk, laptop workspace, free WiFi, bed sheets
Bay Village Suites
2.0 star property
6.2 out of 10, (54)
"For the price, this little gem of a room was perfect for my daughter and I wanting to just spend a few days exploring Boston on foot. "
Bay Village Suites
Interior
Sonder 907 Main
4.0 star property
8.2 out of 10, Very Good, (333)
"Fabulous location and the rooms are awesome. So Boston!!"
The price is ₩402,544
per night
May 27 - May 28
Sonder 907 Main
Property grounds
Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (825)
"Our quick one night stay was great! Dana was very helpful at check in- a map of all the walkable restaurants for dinner and a recommendation for breakfast. The room was clean and the bed was comfortable. Would definitely stay here again."
The price is ₩243,504
per night
May 27 - May 28
Crescent Suites Hotel
Exterior
No. 284 powered by Sonder
4.0 star property
9.4 out of 10, Exceptional, (777)
"Quiet at night yet just one block away from Newbury street with many restaurants, coffee shops and shopping."
The price is ₩390,217
per night
Jun 9 - Jun 10
No. 284 powered by Sonder
Iron/ironing board, free WiFi, bed sheets
Premier Suites - Bay Village
2.0 star property
6.2 out of 10, (78)
"I recently stayed at a hotel in Boston with a bay view. The location of the hotel was great, and it was easy to communicate with the staff. However, I found that the building and room were starting to look tired and could use some updating. On the positive side, there were plenty of things to do in the area, and the check-in process was smooth. Overall, the hotel's location and communication were excellent, but improvements could be made in terms of the building and room condition."
Premier Suites - Bay Village
Rooftop terrace
Global Luxury Suites East Boston
4.0 star property
7.0 out of 10, Good, (85)
" It was very important that I called a week ahead to pay for parking and to make sure a lockbox was ready for us when we arrived after midnight when no one was at the main desk. I had to call again before we got on the plane for our lock box code. It was close to the subway entrance. The pool was in a different building and it was closed for maintenance. The main reason I picked this location was the pool for our son, he was very disappointed."
The price is ₩287,716
per night
May 27 - May 28
Global Luxury Suites East Boston
Iron/ironing board, free WiFi
400 Columbus Avenue
2.0 star property
7.6 out of 10, Good, (52)
"I'm giving this a five-star rating based on the value for the money, not because it is a five-star hotel. It was much less than anything else I could find and it served the purpose. It was clean, had the basic amenities (bed, shower, kitchenette, and Wifi), and is walking distance to restaurants. Given the walkability of Boston, it's not that far from anything. I had a conference at the Harvard Medical School and often walked, sometimes taking an Uber when in a rush (about 1.5 miles)....
The price is ₩228,540
per night
May 27 - May 28
400 Columbus Avenue
Exterior
245 Newbury St
2.0 star property
8.0 out of 10, Very Good, (78)
"Great location, no frill accommodations but it has all the basics. We come to Boston regularly, and you aren’t going to find a better location. If you are looking for an upscale place to stay, this isn’t it. But if you are looking for a clean, nice place with a great location, this is it. "
The price is ₩310,162
per night
May 28 - May 29
245 Newbury St
Front of property
89 Marion
2.0 star property
8.2 out of 10, Very Good, (131)
"Bed is noisy each time you move. TV was not working but the room was clean and in a nice building in a quiet and convenient location."
The price is ₩239,423
per night
May 27 - May 28
89 Marion
Front of property
40 Temple St
2.0 star property
7.8 out of 10, Good, (55)
"Excellent stay in a convenient part of town. Love that everything was online and easy from booking, to checkin, property entry codes to checkout. Will stay again!"
The price is ₩228,540
per night
May 27 - May 28
40 Temple St
Premier Apartment, 3 Bedrooms | Living area | 42-inch flat-screen TV with digital channels, TV, streaming services
Sonder at Pierce Boston
4.0 star property
8.8 out of 10, Excellent, (171)
"Very nice "
The price is ₩572,167
per night
May 27 - May 28
Sonder at Pierce Boston
Apartment | Premium bedding, desk, iron/ironing board, free WiFi
Charlesgate Suites
3.5 star property
9.6 out of 10, Exceptional, (143)
"Great location, walking distance to Fenway. Very pleasant experience, would highly recommend."
Charlesgate Suites
Suite, 1 Double Bed, Accessible | 1 bedroom, individually decorated, individually furnished
Sonder The Magnolia
3.5 star property
9.0 out of 10, Wonderful, (32)
"The room/unit we were in was above shake shack so you could here the music and noise from the restaurant. Location was great for us though it was Midway between fenway and Boston common in back bay. We took the free logan express bus to back bay and the room was 1 block away. Only $3 to go back to the airport. "
The price is ₩600,585
per night
May 27 - May 28
Sonder The Magnolia
Individually decorated, individually furnished, iron/ironing board
Sonder The Hancock
3.5 star property
8.0 out of 10, Very Good, (66)
"Building and street were perfect ! Check in was super easy, "
The price is ₩522,868
per night
May 27 - May 28
Sonder The Hancock
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See all available properties in Winchester
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.

Other types of properties in Winchester you may be interested in

Exterior
Omni Boston Hotel at the Seaport
4.5 star property
9.0 out of 10, Wonderful, (2050)
"The staff was friendly. Our room was super clean, comfy, and had a great view of the city. I loved the floor to ceiling windows. "
The price is ₩268,139
per night
Jun 9 - Jun 10
Omni Boston Hotel at the Seaport
Interior detail
The Dagny Boston
4.0 star property
9.2 out of 10, Wonderful, (3511)
"Dagny was a great stay. Reception staff were excellent and the rooms were fabulous, particularly the beds and bathroom. It can get a little noisy early in the morning with rubbish being emptied from the previous evening but, overall, it's a very good hotel"
The price is ₩280,125
per night
May 27 - May 28
The Dagny Boston
Room, 2 Queen Beds | Desk, laptop workspace, blackout drapes, iron/ironing board
Four Points by Sheraton Boston Newton
3.5 star property
8.2 out of 10, Very Good, (2037)
"Room was very hot, despite our thermostat being set to 60 degrees AC. Smelled like someone smoked in the room prior to us. "
The price is ₩166,549
per night
May 27 - May 28
Four Points by Sheraton Boston Newton
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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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.

Recent reviews of Winchester properties
Expedia verified reviews

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

5/5 Excellent
"Amazing staff. Beautiful hotel"
A verified traveler stayed at Club Quarters Hotel Faneuil Hall, Boston
Posted 1 day ago
Club Quarters Hotel Faneuil Hall, Boston