Winchester Holiday Rentals

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Holiday Rentals in Winchester

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Fridge, microwave, oven, stovetop
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
7.4 out of 10, Good, (28)
"This place was perfect for our Salem visit. Easy to find and convenient for a quick trip to the store. The neighborhood was nice."
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Temple Place Suites
Desk, iron/ironing board, free WiFi, bed sheets
Temple Place Suites
2.5 star property
6.8 out of 10, (93)
"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 HK$963
HK$1,536 total
includes taxes & fees
7 Jul - 8 Jul
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, (425)
"The apartments are updated and beautiful. However, the doors were missing on the one bedroom apartment I reserved. We checked in late that evening, so they weren't able to correct the problem until the next day. There were no other problems. I would stay there again in the future."
The price is HK$1,834
HK$3,087 total
includes taxes & fees
30 Jun - 1 Jul
Global Luxury Suites Downtown Boston
HYATT house Boston/Burlington
Courtyard
HYATT house Boston/Burlington
3.0 star property
9.2 out of 10, Wonderful, (2226)
"The size of the room was really nice. Full kitchen, nice size living space with L shaped couch and large bed room. My only negative point was the only way into the bathroom was through the actual bed room. I had my niece with me who slept on the couch and she had to go through my bedroom area to get to the bathroom. Other than that very nice place! We unfortunately were traveling at busy times and if you are looking to get to downtown Boston it will take you a solid hour to get there during...
The price is HK$1,257
HK$1,404 total
includes taxes & fees
5 Jul - 6 Jul
HYATT house Boston/Burlington
Sonder 907 Main
Interior
Sonder 907 Main
4.0 star property
8.0 out of 10, Very good, (344)
"Nice kettle and fragrant soap"
The price is HK$1,576
HK$1,828 total
includes taxes & fees
3 Jul - 4 Jul
Sonder 907 Main
Crescent Suites Hotel
Property grounds
Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (837)
"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 HK$1,397
HK$1,561 total
includes taxes & fees
30 Jun - 1 Jul
Crescent Suites Hotel
No. 284 powered by Sonder
Exterior
No. 284 powered by Sonder
4.0 star property
9.4 out of 10, Exceptional, (793)
"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 HK$1,718
HK$2,026 total
includes taxes & fees
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, (89)
"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, (143)
"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 HK$1,452
HK$2,320 total
includes taxes & fees
22 Jun - 23 Jun
89 Marion
Maverick Suites at 28 Fenway
Living area
Maverick Suites at 28 Fenway
2.0 star property
9.4 out of 10, Exceptional, (59)
"All was great. "
The price is HK$1,195
HK$2,137 total
includes taxes & fees
2 Jul - 3 Jul
Maverick Suites at 28 Fenway
Sonder at Pierce Boston
Exterior
Sonder at Pierce Boston
4.0 star property
8.8 out of 10, Excellent, (182)
"A very nice small apartment!"
The price is HK$2,311
HK$2,726 total
includes taxes & fees
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, (67)
"We enjoyed our stay!"
The price is HK$1,452
HK$2,387 total
includes taxes & fees
30 Jun - 1 Jul
Maverick Suites at 400 Columbus Ave
Maverick Suites at 245 Newbury St
Exterior
Maverick Suites at 245 Newbury St
2.0 star property
8.2 out of 10, Very good, (87)
"Particularly liked the non-slip shower!"
The price is HK$1,921
HK$2,926 total
includes taxes & fees
30 Jun - 1 Jul
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 HK$2,011
HK$3,209 total
includes taxes & fees
2 Jul - 3 Jul
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 HK$1,921
HK$2,926 total
includes taxes & fees
23 Jun - 24 Jun
Maverick Suites at 40 Temple St
Maverick Suites at 402 Columbus Ave
Private kitchen
Maverick Suites at 402 Columbus Ave
2.0 star property
7.6 out of 10, Good, (40)
"I had trouble at first getting the key pad codes to work, and at one point couldn't find the code. It was not clear if there was ever someone who I could call and get quick help if for some reason I couldn't get into my room,"
The price is HK$1,372
HK$2,296 total
includes taxes & fees
30 Jun - 1 Jul
Maverick Suites at 402 Columbus Ave
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 HK$1,748
HK$2,062 total
includes taxes & fees
9 Jul - 10 Jul
Sonder The Hancock
Sonder The Magnolia
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 HK$2,364
HK$2,789 total
includes taxes & fees
11 Jul - 12 Jul
Sonder The Magnolia
Beautiful Retreat close to Downtown Boston. Pets friendly.
Pool
Beautiful Retreat close to Downtown Boston. Pets friendly.
9.8 out of 10, Exceptional, (86)
"With the traffic in Boston, you can't hardly beat the location. We loved the ease of driving to get to anywhere. Wifi signal was a bit poor in places and we weren't sure what the extra keys were for, but it was a great place to stay!"
The price is HK$1,101
HK$2,684 total
includes taxes & fees
3 Jul - 4 Jul
Beautiful Retreat close to Downtown Boston. Pets friendly.
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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

Omni Boston Hotel at the Seaport
Exterior
Omni Boston Hotel at the Seaport
4.5 star property
9.0 out of 10, Wonderful, (2217)
"Loved this hotel! Staff were awesome! So many staff. Also used spa and ate at the Sporting Club (which was also great except for the runner who slammed our food down in the wrong places without a care). Looking forward to trying more Omni hotels in the future. "
The price is HK$1,574
HK$2,106 total
includes taxes & fees
3 Jul - 4 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, (2686)
"Excellent location "
The price is HK$1,377
HK$1,876 total
includes taxes & fees
4 Jul - 5 Jul
Omni Parker House
The Revolution Hotel
Premium bedding, down duvets, pillow-top beds, in-room safe
The Revolution Hotel
3.5 star property
8.6 out of 10, Excellent, (1553)
"I enjoyed my stay at the Revolution Hotel very much. It's located in a nice part of Boston where you can easily access public transportation or walk."
The price is HK$1,321
HK$1,538 total
includes taxes & fees
30 Jun - 1 Jul
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.

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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 are some of the best holiday rentals that Winchester has to offer?

Beautiful, Cozy Ultra Convenient Salem Home: This holiday home rental outside of Winchester is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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

The Dagny Boston

The Dagny Boston

5/5 Excellent
"Great!"
A verified traveller stayed at The Dagny Boston
Posted 12 hours ago
The Dagny Boston