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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

Compare 6 Hostels in Winchester with updated reviews, rates, and availability.

HI Boston - Hostel
Reception

HI Boston - Hostel

2.0 star property
8.8 out of 10, Excellent, (1002)
"Very nice and well organized hostel offering activities if you wish to socialize. Local dining is within a short walk."
The price is SAR 800
SAR 932 total
includes taxes & fees
4 May - 5 May
HI Boston - Hostel
The Sanctuary at TPH - Boston
Property grounds

The Sanctuary at TPH - Boston

9.8 out of 10, Exceptional, (14)
"The Pershire house was a charming and cozy place to stay. I was there for two weeks in January 2025. I stayed in the Sanctuary Room on the third floor. It was spacious, had a firm mattress excellent for sleeping, and an sitrimg area. The shared bathroom was clean and well-appointed with a lovely modern glass walled shower and nice tiles. The shared kitchen had all the amenities needed to cook (which I did a lot). Lovely living and dining room and washer/dryer also available.The house has...
The price is SAR 375
SAR 668 total
includes taxes & fees
5 May - 6 May
The Sanctuary at TPH - Boston
The Tower Room at TPH - Boston
Property grounds

The Tower Room at TPH - Boston

9.8 out of 10, Exceptional, (19)
"had a great time, instructions provided were very helpful and easy to follow "
The price is SAR 375
SAR 668 total
includes taxes & fees
28 Apr - 29 Apr
The Tower Room at TPH - Boston
The King's Room at TPH - Boston
1 bedroom, in-room safe, iron/ironing board, free WiFi

The King's Room at TPH - Boston

9.2 out of 10, Wonderful, (16)
"We drove through a neighborhood of homes built in the 1800’s to reach Perthshire House. It is also an antique house wears its years with a homey grace and beauty. Yet, it has elegant 21st century amenities. It has a full kitchen with top quality appliances. The bathrooms are luxurious with muted lighting and amazing walk-in showers. There is a comfortable living well suited to reading or conversation. There are two on-premises parking spots that one can rent - well worth the price because the...
The price is SAR 375
SAR 668 total
includes taxes & fees
12 May - 13 May
The King's Room at TPH - Boston
The Sunset Room at TPH - Boston
Smart TV, fireplace

The Sunset Room at TPH - Boston

10.0 out of 10, Exceptional, (11)
"My fiance and i stayed a couple nights for a weekend getaway a"
The price is SAR 375
SAR 668 total
includes taxes & fees
28 Apr - 29 Apr
The Sunset Room at TPH - Boston
Trenton Street Homestay - Hostel
Full-size fridge, microwave, oven, stovetop

Trenton Street Homestay - Hostel

2.0 star property
7.8 out of 10, Good, (9)
"It was perfect clean friendly. Host was better then best. "
Trenton Street Homestay - Hostel
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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Other property types in Winchester

Sonder 907 Main
Lobby

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (467)
"Great Location! Nice rooms. Nice Bar at the lobby and the rooftop"
The price is SAR 710
SAR 824 total
includes taxes & fees
26 May - 27 May
Sonder 907 Main
Maverick Suites at 28 Fenway
Deluxe Studio Suite (2nd Floor - Unit 202) | Individually furnished, iron/ironing board, free WiFi, bed sheets

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (189)
"The property was nice. I was a little amused at the size but it was perfect. There was a "
The price is SAR 383
SAR 806 total
includes taxes & fees
30 Apr - 1 May
Maverick Suites at 28 Fenway
Temple Place Suites
Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

2.5 star property
6.8 out of 10, (198)
"We loved how walkable this location was! It was easy to walk or find public transport for anywhere we needed! "
The price is SAR 495
SAR 776 total
includes taxes & fees
28 Apr - 29 Apr
Temple Place Suites
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.

Frequently asked questions

When is the best time of year to stay in a hostel in Winchester?
The weather is important when you’re experiencing new places, so here’s some information that may be helpful: The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 33°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 5 inches of snowfall.
What is there to see and do in Winchester?
Overall, Winchester is known for its soccer matches, wildlife, and flowers. Major attractions include TD Garden, Fenway Park, and Encore Boston Harbor. Get out into nature with places like Winter Pond, Middlesex Fells Reservation, and Boston Common. Cultural attractions include Somerville Theatre, Harvard Museum of Natural History, and American Repertory Theater.
What's the best way to get to and around Winchester while staying at a hostel?
Keep this information about transit options in and around Winchester in your back pocket to make the most of your stay: You can search for flights to the closest airport, which is Bedford, MA (BED-Laurence G. Hanscom Field), 7.7 mi (12.3 km) away from the city center. An alternative is Boston, MA (BNH-Boston Harbor Seaplane Base), situated 8.4 mi (13.5 km) away. When you’re out and about, you may want to use public transit during your trip. Train stations including Winchester Station and Winchester Wedgemere Station make it easy to explore more of the area.