Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Vacation Rentals in Winchester

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, (203)
"Great stay and close to my monthly event site so I hope to come back again."
The price is NT$6,695
NT$9,278 total
includes taxes & fees
Sep 13 - Sep 14
Premier Suites - Bay Village
Bay Village Suites
1 bedroom, desk, laptop workspace, free WiFi

Bay Village Suites

2.0 star property
6.4 out of 10, (194)
"I like this place and good location!!"
Bay Village Suites
Temple Place Suites
Deluxe Studio | 1 bedroom, desk, iron/ironing board, free WiFi

Temple Place Suites

2.5 star property
7.0 out of 10, Good, (261)
"Conveniently located and easy to find. The owners were incredibly accommodating and always fast to respond. "
The price is NT$3,632
NT$7,789 total
includes taxes & fees
Aug 24 - Aug 25
Temple Place Suites
Maverick Suites at 28 Fenway
Deluxe Studio Suite (2nd Floor - Unit 202) | 1 bedroom, individually furnished, iron/ironing board, free WiFi

Maverick Suites at 28 Fenway

3.0 star property
8.8 out of 10, Excellent, (258)
"Great location "
The price is NT$4,100
NT$7,700 total
includes taxes & fees
Aug 24 - Aug 25
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, (586)
"Staff was very friendly! "
Global Luxury Suites Downtown Boston
Crescent Suites Hotel
Property grounds

Crescent Suites Hotel

3.0 star property
9.6 out of 10, Exceptional, (1064)
"When I return to the area, I will definitely stay here."
Crescent Suites Hotel
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, (517)
"Great hotel!"
The price is NT$6,756
NT$7,834 total
includes taxes & fees
Sep 5 - Sep 6
907 Main Hotel Central Square, Sonder by Marriott Bonvoy
Maverick Suites at 89 Marion
Interior entrance

Maverick Suites at 89 Marion

2.0 star property
8.4 out of 10, Very Good, (248)
"Good nights sleep, cozy, nice amenities. "
The price is NT$4,054
NT$7,260 total
includes taxes & fees
Sep 21 - Sep 22
Maverick Suites at 89 Marion
Maverick Suites at 245 Newbury St
Exterior

Maverick Suites at 245 Newbury St

2.0 star property
8.2 out of 10, Very Good, (139)
"Clean. Great location. "
The price is NT$7,536
NT$11,474 total
includes taxes & fees
Sep 22 - Sep 23
Maverick Suites at 245 Newbury St
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, (260)
"Great apartment in a super convenient location near Fenway and BU. Easy access, clean, great views. Definitely would stay here again!"
The price is NT$7,765
NT$9,159 total
includes taxes & fees
Aug 24 - Aug 25
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
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, (89)
"Very cozy and centrally located. Satellite tv didn’t work. "
The price is NT$6,912
NT$10,757 total
includes taxes & fees
Sep 23 - Sep 24
Maverick Suites at 40 Temple St
Maverick Suites at 402 Columbus Ave
Apartment, 2 Bedrooms | Private kitchen | Mini-fridge, microwave, cookware/dishes/utensils, paper towels

Maverick Suites at 402 Columbus Ave

2.5 star property
7.8 out of 10, Good, (59)
"Easy to walk to and from T stations near by. Decently priced and was overall a great place to stay!"
The price is NT$4,807
NT$8,338 total
includes taxes & fees
Sep 21 - Sep 22
Maverick Suites at 402 Columbus Ave
Global Luxury Suites East Boston
Rooftop terrace

Global Luxury Suites East Boston

4.0 star property
6.8 out of 10, (162)
"All was great, the appartement itself, the location and not the least the use of the gym, dundeck and pool. Really a great place to enjoy Boston!"
The price is NT$7,429
NT$12,054 total
includes taxes & fees
Aug 24 - Aug 25
Global Luxury Suites East Boston
The Chester Hotel
City Studio | 1 bedroom, Egyptian cotton sheets, premium bedding, memory foam beds

The Chester Hotel

4.0 star property
9.0 out of 10, Wonderful, (18)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
The price is NT$5,558
NT$11,836 total
includes taxes & fees
Aug 24 - Aug 25
The Chester Hotel
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, (118)
"Property is located in a very nice area. No frill, what they advertise, you get. "
The price is NT$4,729
NT$8,248 total
includes taxes & fees
Sep 22 - Sep 23
Maverick Suites at 400 Columbus Ave
Charlesgate Suites
Apartment | 1 bedroom, premium bedding, desk, iron/ironing board

Charlesgate Suites

3.5 star property
9.4 out of 10, Exceptional, (184)
"Awesome property, conveniently located near everything, especially Fenway. Definitely will stay here again. "
The price is NT$7,093
NT$13,424 total
includes taxes & fees
Sep 2 - Sep 3
Charlesgate 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, (927)
"Beautiful property "
The price is NT$8,102
NT$9,556 total
includes taxes & fees
Aug 24 - Aug 25
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
The Monty Boston
Luxury Suite 2 | Living area | Smart TV, Netflix, Hulu, streaming services

The Monty Boston

2.5 star property
9.6 out of 10, Exceptional, (20)
"Everything was great to live in this place! Very spacious and convenient."
The price is NT$16,815
NT$24,600 total
includes taxes & fees
Sep 10 - Sep 11
The Monty Boston
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, (69)
"Great place , size of the apartment , very clean"
The price is NT$9,563
NT$11,279 total
includes taxes & fees
Sep 23 - Sep 24
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
Apartments in Salem
First Floor 3-4 Bedrooms Apartment | Private kitchen | Fridge, microwave, coffee/tea maker, toaster

Apartments in Salem

3.0 star property
8.0 out of 10, Very Good, (46)
"Property was fine. It is well located to see the sites in Salem. Only negative was that the neighbors were a bit loud at night. "
Apartments in Salem
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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Top Winchester Hotel Reviews

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Loved this hotel which is an old converted warehouse. Very convenient for hop on/off trolley bus. Reception staff were exceptionally friendly and helpful."
Annette 2-night trip
Posted 16 hours ago
Harborside Inn Of Boston

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we have vacation rentals in Winchester close to Winter Pond, or you can choose a more remote option if you're looking for a relaxing stay. Winchester is known for its soccer 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 vacation rentals like in Winchester?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Winchester. Vacation rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.