Winchester Holiday Rentals

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Holiday Rentals in Winchester

Sonder 907 Main

4.0 star property
8.2 out of 10, Very good, (432)
"The property was close to anything you could need and all processes were beyond easy. Having all access on your phone was amazing. "
The price is AU$235
includes taxes & fees
18 Feb - 19 Feb
Sonder 907 Main

No. 284 powered by Sonder

4.0 star property
9.4 out of 10, Exceptional, (868)
"my favorite stay ever. i loved my stay and everything about it and can’t wait to come back soon. "
The price is AU$286
includes taxes & fees
17 Feb - 18 Feb
No. 284 powered by Sonder

Temple Place Suites

2.5 star property
6.8 out of 10, (182)
"Insane lil spot for seeing Boston and surrounding areas!"
The price is AU$260
includes taxes & fees
17 Feb - 18 Feb
Temple Place Suites

Global Luxury Suites Downtown Boston

4.0 star property
8.0 out of 10, Very good, (528)
"Apartment was spotless, had everything you could need, spacious../but the TV didn’t work. "
The price is AU$379
includes taxes & fees
23 Feb - 24 Feb
Global Luxury Suites Downtown Boston

Bay Village Suites

2.0 star property
6.2 out of 10, (149)
"It was a clean place, but the shared bathroom door didn’t close properly, and the heater wasn’t working well, I had to sleep with my jacket on plus it was super noisy and would turn on and off automatically so I was constantly waking up scared. There’s no check-in desk, so everything is handled via email. While the staff responded quickly, the process felt less flexible. I would recommend for a few days. "
Bay Village Suites

Sonder at Pierce Boston

4.0 star property
8.8 out of 10, Excellent, (218)
"We loved the Sonder on Pierce, it was a beautiful apartment, good facilities and easy food options nearby "
The price is AU$303
includes taxes & fees
24 Feb - 25 Feb
Sonder at Pierce Boston

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (164)
"all good"
The price is AU$374
includes taxes & fees
24 Feb - 25 Feb
Maverick Suites at 28 Fenway

Premier Suites - Bay Village

2.0 star property
6.2 out of 10, (140)
"I liked everything, except that in our there was a noise because of the wind, it sounded like mice but we realized it was just the wind that entered through a hole in the wall I think, other than that, amazing staying!"
Premier Suites - Bay Village

Global Luxury Suites East Boston

4.0 star property
7.0 out of 10, Good, (128)
"This was the perfect stay for what we needed. It was what we expected. The pictures are very accurate. Highly recommend the garage parking. Easy access to room from garage. The T is super close which makes travel around the city super convenient. Would stay at the same location again but would try to request a room with a view of the harbor/city. "
The price is AU$426
includes taxes & fees
24 Feb - 25 Feb
Global Luxury Suites East Boston

Sonder The Magnolia

3.5 star property
9.0 out of 10, Wonderful, (52)
"Sensational location "
The price is AU$293
includes taxes & fees
11 Mar - 12 Mar
Sonder The Magnolia

Maverick Suites at 89 Marion

2.0 star property
8.4 out of 10, Very good, (208)
"Great hotel for the price and location. Would have love to know where we can park in the area. "
The price is AU$338
includes taxes & fees
19 Mar - 20 Mar
Maverick Suites at 89 Marion

Maverick Suites at 40 Temple St

2.0 star property
7.6 out of 10, Good, (73)
"Absolutely LOVED this property. So modern & charming, in a location that’s very walkable to many great attractions in Boston. My only qualm with this location is the lack of parking - we unfortunately spent a lot of extra $$ on parking. However, I’d visit again & not bring my car to avoid this. "
The price is AU$387
includes taxes & fees
17 Mar - 18 Mar
Maverick Suites at 40 Temple St

"Travelers' Choice Award" Green Turtle I Houseboat in Boston Harbor!

10.0 out of 10, Exceptional, (209)
"I enjoyed it. "
The price is AU$627
includes taxes & fees
17 Feb - 18 Feb
"Travelers' Choice Award" Green Turtle I Houseboat in Boston Harbor!

Maverick Suites at 400 Columbus Ave

2.0 star property
7.4 out of 10, Good, (98)
"Having to have cleaning of the room as an extra charge should be noted clearly for any future occupants. The unit is not close to any restaurant or store unless you want to walk 10 minutes to get there and carry anything back. It is not convenient to anything of note. Would not stay there again. It was clean but that's the best I could say for the property. "
The price is AU$358
includes taxes & fees
17 Mar - 18 Mar
Maverick Suites at 400 Columbus Ave

"Travelers Choice Award" Spacious 2 bedrm 45 ft yacht close to the Freedom Trail

10.0 out of 10, Exceptional, (104)
"Everything about our stay was wonderful. Perfect location. We could walk everywhere. Our hosts were warm and wonderful and we enjoyed the yacht. Perfect after a long day sight seeing!!"
"Travelers Choice Award" Spacious 2 bedrm 45 ft yacht close to the Freedom Trail

Sonder The Hancock

3.5 star property
7.8 out of 10, Good, (86)
"Lovely weeks stay at the Hancock. Great facilities in the apartment and excellent location. The only suggestion I'd make is to add a floor length mirror and have some English tea bags available. "
The price is AU$288
includes taxes & fees
10 Mar - 11 Mar
Sonder The Hancock

Downtown Studio, Abundant Natural Light

4.6 out of 10, (4)
"Clean, great location. Bad communication on how to get keys. Traveling from out of town, asked for early check in. Denied. I get it. They sent info that I would need to get keys from a kiosk. No location sent on kiosk. Figured it was so I would not check in early. Got to south station around 2. Made my way down to the address for the apartment, because I had no response to messages asking for the location of the kiosk. Got to the apartment location at 3. Called. Talked to an agent for 20 minutes...
Downtown Studio, Abundant Natural Light

Amazing price and location / parking -North End (M1S)

9.6 out of 10, Exceptional, (39)
"Cute studio on the heart of the North End! Excellent communication with the property manager who was very responsive to our needs! I loved it so much, we booked the stilstudio and extra 2 days at the end of our trip! "
Amazing price and location / parking -North End (M1S)

Maverick Suites at 245 Newbury St

2.0 star property
8.2 out of 10, Very good, (117)
"Excellent "
The price is AU$438
includes taxes & fees
17 Feb - 18 Feb
Maverick Suites at 245 Newbury St

Fun houseboat. Walk to Boston attractions WIFI

9.8 out of 10, Exceptional, (63)
"This houseboat is a perfect alternative to a hotel, such a fun experience. The location is perfect too. Highly recommend "
The price is AU$760
includes taxes & fees
4 Mar - 5 Mar
Fun houseboat. Walk to Boston attractions WIFI
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 types of properties in Winchester you may be interested in

Hilton Boston Park Plaza

4.0 star property
8.4 out of 10, Very good, (3331)
"Great night stay "
The price is AU$255
includes taxes & fees
23 Feb - 24 Feb
Hilton Boston Park Plaza

Harborside Inn Of Boston

4.0 star property
9.2 out of 10, Wonderful, (4768)
"Great location"
The price is AU$200
includes taxes & fees
23 Feb - 24 Feb
Harborside Inn Of Boston

Omni Boston Hotel at the Seaport

4.0 star property
9.2 out of 10, Wonderful, (3239)
"Please fix the coffee machines! And no HEAT in the room"
The price is AU$411
includes taxes & fees
23 Feb - 24 Feb
Omni Boston Hotel at the Seaport
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

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?

Modern & Walkable to city sights. A 4-bedroom house in wonderful Boston: This holiday home rental outside of Winchester is equipped with a selection of games, 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.