Winchester Holiday Rentals

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Check prices for these dates

Tonight
1 Jul - 2 Jul
Tomorrow
2 Jul - 3 Jul
This weekend
4 Jul - 6 Jul
Next weekend
11 Jul - 13 Jul

Holiday Rentals in Winchester

Temple Place Suites
1 bedroom, desk, iron/ironing board, free WiFi

Temple Place Suites

2.5 star property
6.8 out of 10, (235)
"Near Boston Commons was very nice"
The price is S$204
includes taxes & fees
2 Jul - 3 Jul
Temple Place Suites
Premier Suites - Bay Village
1 bedroom, iron/ironing board, free WiFi, bed sheets

Premier Suites - Bay Village

2.0 star property
6.2 out of 10, (171)
"Excellent place, there is no noise and it is close to everything... I arrived at the place in the early morning and never saw anything out of the ordinary in the area so it is a quiet area."
The price is S$148
includes taxes & fees
3 Jul - 4 Jul
Premier Suites - Bay Village
Maverick Suites at 28 Fenway
1 bedroom, individually furnished, iron/ironing board, free WiFi

Maverick Suites at 28 Fenway

3.0 star property
8.8 out of 10, Excellent, (233)
"If you need a place to sleep close to Fenway this is the perfect place."
The price is S$281
includes taxes & fees
2 Jul - 3 Jul
Maverick Suites at 28 Fenway
Global Luxury Suites Downtown Boston
Lobby lounge

Global Luxury Suites Downtown Boston

4.0 star property
8.0 out of 10, Very good, (563)
"Very clean, safe, and convenient. Beautiful accommodations."
Global Luxury Suites Downtown Boston
Crescent Suites Hotel
Property grounds

Crescent Suites Hotel

3.0 star property
9.6 out of 10, Exceptional, (1038)
"It was very nice, the riverwalk in the back was a good way for us to stretch our legs."
Crescent Suites Hotel
Bay Village Suites
1 bedroom, desk, laptop workspace, free WiFi

Bay Village Suites

2.0 star property
6.4 out of 10, (168)
"Easy check-in, clean. "
Bay Village Suites
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
Individually furnished, laptop workspace, iron/ironing board, bed sheets

No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy

4.0 star property
9.4 out of 10, Exceptional, (910)
"Great location, clean room and had everything we needed "
The price is S$328
includes taxes & fees
2 Jul - 3 Jul
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
907 Main Hotel Central Square, Sonder by Marriott Bonvoy
Lobby

907 Main Hotel Central Square, Sonder by Marriott Bonvoy

4.0 star property
8.2 out of 10, Very good, (497)
"We really enjoyed our stay. It was an apartment feel in a great area of Cambridge "
The price is S$290
includes taxes & fees
2 Jul - 3 Jul
907 Main Hotel Central Square, Sonder by Marriott Bonvoy
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
Property amenity

Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway

4.0 star property
8.8 out of 10, Excellent, (252)
"Great apartment in a super convenient location near Fenway and BU. Easy access, clean, great views. Definitely would stay here again!"
The price is S$276
includes taxes & fees
2 Jul - 3 Jul
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
View from property

Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay

3.5 star property
8.8 out of 10, Excellent, (63)
"Great place , size of the apartment , very clean"
The price is S$358
includes taxes & fees
2 Jul - 3 Jul
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
Maverick Suites at 400 Columbus Ave
42-inch TV with satellite channels

Maverick Suites at 400 Columbus Ave

2.0 star property
7.4 out of 10, Good, (114)
"Property is located in a very nice area. No frill, what they advertise, you get. "
The price is S$318
includes taxes & fees
30 Jul - 31 Jul
Maverick Suites at 400 Columbus Ave
Maverick Suites at 89 Marion
Front of property

Maverick Suites at 89 Marion

2.0 star property
8.4 out of 10, Very good, (243)
"Well kept old building with nice features "
The price is S$370
includes taxes & fees
30 Jul - 31 Jul
Maverick Suites at 89 Marion
Global Luxury Suites East Boston
Rooftop terrace

Global Luxury Suites East Boston

4.0 star property
7.0 out of 10, Good, (146)
"Amazing location right by the water, quiet building and clean. But the furniture is really uncomfortable, particularly the couch which is the only seating, it’s a pull out bed so the entire sofa sinks in low. The bed isn’t solid and easily slides off the frame just by sitting on it. We also had a delivery order stolen from the front desk area. "
The price is S$402
includes taxes & fees
6 Jul - 7 Jul
Global Luxury Suites East Boston
Maverick Suites at 245 Newbury St
Exterior

Maverick Suites at 245 Newbury St

2.0 star property
8.2 out of 10, Very good, (135)
"We had no issues, felt at home, enjoyed the quiet, unit perfect for two "
The price is S$475
includes taxes & fees
30 Jul - 31 Jul
Maverick Suites at 245 Newbury St
The Monty Boston
Living area

The Monty Boston

4.0 star property
9.6 out of 10, Exceptional, (18)
"Great spot!"
The price is S$1,023
includes taxes & fees
6 Jul - 7 Jul
The Monty Boston
Maverick Suites at 402 Columbus Ave
Private kitchen

Maverick Suites at 402 Columbus Ave

2.5 star property
7.8 out of 10, Good, (55)
"Location was perfect. Walking distance to so many things!! The kitchen could have been a little bit better stocked. No coffee or salt and pepper. "
The price is S$417
includes taxes & fees
30 Jul - 31 Jul
Maverick Suites at 402 Columbus Ave
Maverick Suites at 40 Temple St
Front of property

Maverick Suites at 40 Temple St

2.0 star property
7.4 out of 10, Good, (86)
"Very cozy and centrally located. Satellite tv didn’t work. "
The price is S$463
includes taxes & fees
30 Jul - 31 Jul
Maverick Suites at 40 Temple St
Charlesgate Suites
1 bedroom, premium bedding, desk, iron/ironing board

Charlesgate Suites

3.5 star property
9.4 out of 10, Exceptional, (182)
"Wonderful experience. Spacious property in a great location. It’s right by BU housing and had a lot of walkable amenities and was close to the T station. "
The price is S$523
includes taxes & fees
2 Jul - 3 Jul
Charlesgate Suites
The Chester Hotel
1 bedroom, Egyptian cotton sheets, premium bedding, memory-foam beds

The Chester Hotel

3.5 star property
8.8 out of 10, Excellent, (16)
"Excellent property, well appointed, clean and with all the essentials for a comfortable stay. Close to public transportation and several restaurants and eateries nearby. Easy check in and out. The only negative is the city noise: sirens, traffic, etc. but that comes with the convenience of being in the city."
The price is S$490
includes taxes & fees
2 Jul - 3 Jul
The Chester Hotel
Furnished Apartments near Encore Boston
1 bedroom, desk, laptop workspace, free WiFi

Furnished Apartments near Encore Boston

2.5 star property
6.0 out of 10, (2)
The price is S$279
includes taxes & fees
2 Jul - 3 Jul
Furnished Apartments near Encore Boston
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 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.