Search Holiday Rentals in Winchester

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Top Holiday Rentals in Winchester

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
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 ₹14,946
per night
27 May - 28 May
Crescent Suites Hotel
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
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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 ₹22,917
per night
7 Jun - 8 Jun
No. 284 powered by Sonder
Courtyard
HYATT house Boston/Burlington
3.0 star property
9.2 out of 10, Wonderful, (2203)
"Very clean and comfortable "
The price is ₹13,276
per night
27 May - 28 May
HYATT house Boston/Burlington
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 ₹36,864
per night
27 May - 28 May
Sonder The Magnolia
Apartment, 2 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, (170)
"Very nice "
The price is ₹35,120
per night
27 May - 28 May
Sonder at Pierce Boston
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 ₹24,708
per night
27 May - 28 May
Sonder 907 Main
Front of property
89 Marion
2.0 star property
8.2 out of 10, Very good, (131)
"Good property in great walkable neighborhood. A little noise from the upstairs people on the floors but all manageable. Highly recommend."
The price is ₹15,531
per night
21 May - 22 May
89 Marion
Lobby lounge
Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very good, (409)
"Decent place"
The price is ₹15,894
per night
27 May - 28 May
Global Luxury Suites Downtown Boston
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 ₹16,533
per night
28 May - 29 May
245 Newbury St
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 ₹32,717
per night
19 May - 20 May
Sonder The Hancock
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 ₹16,533
per night
27 May - 28 May
40 Temple St
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 ₹14,362
per night
27 May - 28 May
400 Columbus Avenue
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 ₹15,894
per night
27 May - 28 May
Global Luxury Suites East Boston
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 ₹12,191
per night
2 Jun - 3 Jun
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
Iron/ironing board, free WiFi, bed sheets
Premier Suites - Bay Village
2.0 star property
6.2 out of 10, (77)
"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
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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

Interior detail
The Dagny Boston
4.0 star property
9.2 out of 10, Wonderful, (3507)
"Clean, friendly staff, excellent location to everything!"
The price is ₹17,194
per night
27 May - 28 May
The Dagny Boston
Exterior
Omni Boston Hotel at the Seaport
4.5 star property
9.0 out of 10, Wonderful, (2047)
"Very nice hotel. My new go to whenever I’m in town. "
The price is ₹16,461
per night
9 Jun - 10 Jun
Omni Boston Hotel at the Seaport
Meeting facility
Hilton Boston Park Plaza
4.0 star property
8.4 out of 10, Very good, (3319)
"Always love staying there, bar is great and it’s close to everything. My room this time was on the small side and bathroom was too tight for 2 people."
The price is ₹15,619
per night
27 May - 28 May
Hilton Boston Park Plaza
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.

Holiday Rentals in Winchester

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

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

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

Harborside Inn Of Boston

Harborside Inn Of Boston

5/5 Excellent
"Great location! Cute property, no nonsense frills but very comfortable stay. Larger rooms than I’ve had in Boston before. "
A verified traveller stayed at Harborside Inn Of Boston
Posted 15 hours ago
Harborside Inn Of Boston