A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Winchester vacation rentals

A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

1. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (660 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is P17,239
P19,817 total
includes taxes & fees
Sep 6 - Sep 7
Marriott Vacation Club® at Custom House, Boston
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

2. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,259 reviews)
"The hotel was conveniently located with lots of good dining options nearby. The room was very clean, quiet and comfortable ."
United States
CHRISTINE
The price is P9,931
P11,093 total
includes taxes & fees
Sep 20 - Sep 21
Crescent Suites Hotel
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

3. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (331 reviews)
"Lovely apartment and great stay. Location is very good with lots to do around"
United States
Obianuju
The price is P6,056
P10,155 total
includes taxes & fees
Aug 28 - Aug 29
Premier Suites - Bay Village
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

4. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (309 reviews)
"Amazing location we loved it"
United States
MARLYN
The price is P8,056
P15,647 total
includes taxes & fees
Sep 21 - Sep 22
Kasa Boston at Fenway
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

5. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (410 reviews)
"Good clear communication. Great location! Walked to Fenway for a game. All kinds of restaurants close. Nice clean, comfortable room in a beautifully maintained building!"
United States
James
The price is P9,617
P17,078 total
includes taxes & fees
Aug 30 - Aug 31
Maverick Suites at 28 Fenway
A modern hotel room with a bed, a desk, a sofa, and a dining area.

6. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (228 reviews)
"Kitchen is excellent and rooms excellent"
United States
AKIN
The price is P14,610
P27,424 total
includes taxes & fees
Sep 8 - Sep 9
Charlesgate Suites
A row of brick buildings with storefronts, including a bakery and a liquor store.

7. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very Good, (201 reviews)
"Great location, really cool place!"
United States
lane
The price is P9,223
P16,279 total
includes taxes & fees
Aug 31 - Sep 1
Maverick Suites at 245 Newbury St
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

8. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (452 reviews)
"Great location so close to everything"
United States
Hunter
The price is P5,992
P10,785 total
includes taxes & fees
Aug 30 - Aug 31
Temple Place Suites
A white table with a vase of white orchids, a white chair, and a view of a cityscape through a window with a black frame.

9. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.6 out of 10, Good, (168 reviews)
"Well located"
United States
Evelyn
The price is P9,099
P16,128 total
includes taxes & fees
Aug 29 - Aug 30
Maverick Suites at 400 Columbus Ave
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

10. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (37 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is P11,429
P20,933 total
includes taxes & fees
Sep 8 - Sep 9
The Chester Hotel
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

11. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (142 reviews)
"Worth the stay"
Canada
Akansha
The price is P8,667
P15,640 total
includes taxes & fees
Aug 30 - Aug 31
Maverick Suites at 40 Temple St
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

12. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (17 reviews)
"Great room! Cool place to stay. We walked everywhere and stuff was close by. Woud stay here again"
United States
Cotie
The price is P11,429
P20,933 total
includes taxes & fees
Sep 8 - Sep 9
The Concord Hotel
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

13. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very Good, (737 reviews)
"Great for the price; central to everything"
United States
afshin
The price is P11,634
P20,809 total
includes taxes & fees
Sep 13 - Sep 14
Global Luxury Suites Downtown Boston
A modern kitchen with a central island, a dining area with a round table and chairs, and a large window providing a view of the city at night.

14. The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (40 reviews)
"This place is absolutely stunning I would definitely book again. "
United States
Klaudia
The price is P39,281
P55,783 total
includes taxes & fees
Aug 31 - Sep 1
The Monty Boston
A wooden hallway with a patterned floor leading to a door.

15. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very Good, (310 reviews)
"Stayed in the economy suite, very suitable for a couple! Very clean room and I have never had an easier check-in process!!"
United States
Paula
The price is P8,156
P14,619 total
includes taxes & fees
Aug 30 - Aug 31
Maverick Suites at 89 Marion

16. Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (19 reviews)
"Great location to fenway. Easy and clean."
United States
Allison
The price is P18,001
P27,424 total
includes taxes & fees
Sep 7 - Sep 8
Symple Live
A living room with a black leather sofa, a glass coffee table, a brick fireplace, and a TV mounted on the wall.

17. Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
8.0 out of 10, Very Good, (82 reviews)
"It was very close to stores to go shopping and amazing spot to get last minute reservations for dinner"
United States
Talyciah
The price is P10,168
P17,365 total
includes taxes & fees
Aug 30 - Aug 31
Maverick Suites at 402 Columbus Ave
A hotel room with a large bed, two bedside lamps, a headboard, a wall-mounted abstract art piece, and potted plants.

18. Furnished Apartment Near Longwood

Furnished Apartment Near Longwood
3.0 star property
North Brookline
7.0 out of 10, Good, (6 reviews)
"Easy to check in, students friendly apartment, convenient location, easy to call Uber or Lyft, and within 20 min. drive to the famous universities."
United States
Sujiang
The price is P15,782
P25,903 total
includes taxes & fees
Aug 28 - Aug 29
Furnished Apartment Near Longwood
A spacious indoor swimming pool with large windows, modern seating, and a wooden ceiling.

19. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (205 reviews)
"Good place and nice location but bed sheets and pillows were stained and had hair on them which is unacceptable."
United Kingdom
Leigh
The price is P11,001
P19,742 total
includes taxes & fees
Aug 31 - Sep 1
Global Luxury Suites East Boston

20. Apt in Historic Lynn Neighborhood: 5 Mi to Salem!

Apt in Historic Lynn Neighborhood: 5 Mi to Salem!
3.0 star property
Lynn
The price is P11,174
P25,099 total
includes taxes & fees
Sep 2 - Sep 3
Apt in Historic Lynn Neighborhood: 5 Mi to 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
"This hotel is in a great downtown location with a quick park area to drop off luggage, and a parking garage was just a few blocks from there. A car is NOT needed in Boston... such a walkable town. So easy to find places to eat, both cafes in the mornings and lunch and dinner spots near this hotel and pretty much no matter where we went in Boston, it was easy to find many options for meals. The lobby was inviting with places to sit, iced lemon water available, and friendly helpful staff each time we interacted with them. The 2 elevators were fast. Our room was well appointed and very clean. It was also quiet at night. We appreciated the various lighting options in the room AND that all were on dimmer switches! Bathroom was small - hard for 2 people to maneuver in and out of shower, but the shower stall itself was of good size. And their towels were of nice quality. Bed was comfortable. We would definitely stay there again."
Deborah 3-night trip
Posted 2 hours ago
Harborside Inn Of Boston

Find out more about Winchester

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

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Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we have vacation rentals in Winchester close to Griffin Photography Museum, 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.

How many vacation rentals are there in Winchester?

Choose from 3 Expedia vacation rentals in Winchester for a memorable vacation.

What can I see and do in Winchester?

While exploring the area, visit family-friendly sights like Winter Pond, or get outside and enjoy nature at Boston Common. 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.