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Top Holiday Rentals in Winchester

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, (92)
"Easily understood instructions for access to building and room. Great location. Bathrooms were not always clean. No windows in room. Good value for price"
The price is ฿3,925
per night
17 Jun - 18 Jun
Temple Place Suites
Global Luxury Suites Downtown Boston
Lobby lounge
Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very good, (421)
"Close to good food and short walks to everywhere we wanted to go. Room seemed recently "Renoed". "
The price is ฿8,502
per night
16 Jun - 17 Jun
Global Luxury Suites Downtown Boston
HYATT house Boston/Burlington
Courtyard
HYATT house Boston/Burlington
3.0 star property
9.2 out of 10, Wonderful, (2222)
"Roads around the property are in terrible shape, lots of filled in pot holes."
The price is ฿5,905
per night
5 Jul - 6 Jul
HYATT house Boston/Burlington
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Sonder 907 Main
Interior
Sonder 907 Main
4.0 star property
8.0 out of 10, Very good, (344)
"Fabulous location and the rooms are awesome. So Boston!!"
The price is ฿6,815
per night
2 Jul - 3 Jul
Sonder 907 Main
Crescent Suites Hotel
Property grounds
Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (835)
"We only stayed one night but would absolutely book this place again. Rooms are spacious and clean. Dana is professional and friendly. Highly recommend the Crescent hotel "
The price is ฿6,580
per night
16 Jun - 17 Jun
Crescent Suites Hotel
No. 284 powered by Sonder
Exterior
No. 284 powered by Sonder
4.0 star property
9.4 out of 10, Exceptional, (791)
"Location, location and location! The best location. The only cons were the hallway carpets were very dirty and the recycle/ trash trucks were coming every early morning to the alley to pick up the trash/ recyclables and it was so loud, even closed windows were not helping."
The price is ฿7,278
per night
1 Jul - 2 Jul
No. 284 powered by Sonder
Bay Village Suites
Desk, laptop workspace, free WiFi, bed sheets
Bay Village Suites
2.0 star property
6.2 out of 10, (65)
"Location great. "
Bay Village Suites
Premier Suites - Bay Village
Iron/ironing board, free WiFi, bed sheets
Premier Suites - Bay Village
2.0 star property
6.0 out of 10, (87)
"Close to downtown very easy to get around."
Premier Suites - Bay Village
89 Marion
Front of property
89 Marion
2.0 star property
8.4 out of 10, Very good, (142)
"No complaints about the accommodation, but assessing a so-called, and exorbitant, "property fee" for one night is outrageous. There was no explanation for what this covers. It amounts to a nuisance fee, and unless it is done away with, I won't be staying here again. "
The price is ฿4,365
per night
17 Jun - 18 Jun
89 Marion
Maverick Suites at 28 Fenway
Deluxe Studio Suite | Living area
Maverick Suites at 28 Fenway
2.0 star property
9.4 out of 10, Exceptional, (58)
"All was great. "
The price is ฿4,541
per night
17 Jun - 18 Jun
Maverick Suites at 28 Fenway
Sonder at Pierce Boston
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, (178)
"Staff was great."
The price is ฿10,929
per night
1 Jul - 2 Jul
Sonder at Pierce Boston
Maverick Suites at 400 Columbus Ave
Iron/ironing board, free WiFi
Maverick Suites at 400 Columbus Ave
2.0 star property
7.6 out of 10, Good, (65)
"We enjoyed our stay!"
The price is ฿4,365
per night
17 Jun - 18 Jun
Maverick Suites at 400 Columbus Ave
Maverick Suites at 245 Newbury St
Exterior
Maverick Suites at 245 Newbury St
2.0 star property
8.0 out of 10, Very good, (84)
"Loved this unique stay. The sink is a bit small for women with toiletries. No full-length mirror. But hard to beat this great location. Wonderful stay in this little spot. "
The price is ฿4,805
per night
17 Jun - 18 Jun
Maverick Suites at 245 Newbury St
Global Luxury Suites East Boston
Rooftop terrace
Global Luxury Suites East Boston
4.0 star property
6.8 out of 10, (91)
"Location "
The price is ฿10,695
per night
19 Jun - 20 Jun
Global Luxury Suites East Boston
Maverick Suites at 40 Temple St
Front of property
Maverick Suites at 40 Temple St
2.0 star property
7.8 out of 10, Good, (56)
"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 ฿4,915
per night
16 Jun - 17 Jun
Maverick Suites at 40 Temple St
Sonder The Hancock
Individually decorated, individually furnished, iron/ironing board
Sonder The Hancock
3.5 star property
8.0 out of 10, Very good, (68)
"Nice property "
The price is ฿8,214
per night
7 Jul - 8 Jul
Sonder The Hancock
Sonder The Magnolia
Suite, 1 Double Bed, Accessible | 1 bedroom, individually decorated, individually furnished
Sonder The Magnolia
3.5 star property
9.2 out of 10, Wonderful, (35)
"The location is excellent, close to everything you need. The windows are highly effective at blocking out noise from the busy street. As advertised, there is no elevator and no stove, but the air fryer provided is very convenient. The space is clean and quiet, with a good shower and a comfortable bed. The hallway luggage lockers were a lifesaver. What could be improved: - A full-length mirror or one in the hallway would be beneficial. - Providing communal-size body lotion, similar to the...
The price is ฿10,703
per night
7 Jul - 8 Jul
Sonder The Magnolia
Charlesgate Suites
Apartment | Premium bedding, desk, iron/ironing board, free WiFi
Charlesgate Suites
3.5 star property
9.6 out of 10, Exceptional, (148)
"My daughter and I stayed here for a couple days while she was checking out BU. It’s a great location near the university. Beautiful old building and recently renovated. We contacted the hotel a couple times and they were quick to respond and very friendly. I hope to stay here again in the future. "
Charlesgate Suites
182 Heath st
Fridge, microwave, oven, cookware/dishes/utensils
182 Heath st
2.0 star property
5.0 out of 10, (2)
"Es establecimiento que está muy cerca de la línea naranja del metro y que tiene lo básico para descansar "
182 Heath st
Don't see what you're looking for?
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

Omni Boston Hotel at the Seaport
Exterior
Omni Boston Hotel at the Seaport
4.5 star property
9.0 out of 10, Wonderful, (2180)
"Very nice stay at the Omni Great hotel and location for meetings and conferences. "
The price is ฿7,645
per night
6 Jul - 7 Jul
Omni Boston Hotel at the Seaport
Omni Parker House
Front of property – evening/night
Omni Parker House
4.0 star property
8.8 out of 10, Excellent, (2693)
"Elegant building, historical, clean, best and most convenient location. "
The price is ฿6,279
per night
7 Jul - 8 Jul
Omni Parker House
The Revolution Hotel
Deluxe Room, 2 Double Beds (Bath in Room) | Premium bedding, down duvets, pillow-top beds, in-room safe
The Revolution Hotel
3.5 star property
8.6 out of 10, Excellent, (1554)
"Great location. Easy to get around on foot. Very clean, polite and helpful staff. Was skeptical at first but shared bathrooms are just fine. Would definitely stay again."
The price is ฿6,719
per night
16 Jun - 17 Jun
The Revolution Hotel
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.

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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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 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 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.

Recent reviews of Winchester properties
Expedia verified reviews

Encore Boston Harbor

Encore Boston Harbor

5/5 Excellent
"Beautiful hotel very clean and nice restaurants and casino"
A verified traveller from NEW YORK stayed at Encore Boston Harbor
Posted 13 hours ago
Encore Boston Harbor