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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Winchester vacation rentals

An outdoor patio with round tables and chairs, surrounded by green umbrellas.

1. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,313 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is NT$4,892
NT$5,464 total
includes taxes & fees
Oct 31 - Nov 1
Crescent Suites Hotel
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

2. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (675 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is NT$10,582
NT$12,164 total
includes taxes & fees
Oct 30 - Oct 31
Marriott Vacation Club® at Custom House, Boston
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

3. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (330 reviews)
"Absolutely gorgeous apartments! Concierge was very friendly!"
United States
Kelly
The price is NT$5,789
NT$9,982 total
includes taxes & fees
Nov 9 - Nov 10
Kasa Boston at Fenway
A modern living room with a round dining table, grey sofas, and large windows offering city views.

4. Furnished Apts near Harvard Stadium

Furnished Apts near Harvard Stadium
2.0 star property
Allston
8.6 out of 10, Excellent, (17 reviews)
"spacious, clean, central location"
United States
Gregory
Furnished Apts near Harvard Stadium
A wooden hallway with a patterned floor leading to a door.

5. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (337 reviews)
"Area is quiet, building is modern, super clean and roomy. Plenty of places to eat within walking distance. Green line is an easy, short walk. Elevator wasn't working, but we were notified ahead of time and we easily managed the one flight of stairs. Would stay here again."
United States
Katerina
The price is NT$3,283
NT$6,542 total
includes taxes & fees
Nov 15 - Nov 16
Maverick Suites at 89 Marion
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

6. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (40 reviews)
"Location was very loud but thank God for earplugs. It was very clean but very old. Very expensive for such a location and room. I always believe in paying for what u get but I paid a lot for 3 nights."
United States
Luda
The price is NT$4,100
NT$8,780 total
includes taxes & fees
Nov 3 - Nov 4
The Chester Hotel
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

7. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (763 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is NT$4,342
NT$8,818 total
includes taxes & fees
Nov 10 - Nov 11
Global Luxury Suites Downtown Boston
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

8. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (445 reviews)
"Great price for the place given the location."
United States
Beenish
The price is NT$4,313
NT$8,100 total
includes taxes & fees
Nov 1 - Nov 2
Maverick Suites at 28 Fenway
A hotel room with a large bed, two bedside lamps, a headboard, a wall-mounted abstract art piece, and potted plants.

9. Furnished Apartment Near Longwood

Furnished Apartment Near Longwood
3.0 star property
North Brookline
8.2 out of 10, Very good, (12 reviews)
"Great place, clean, well maintained and centrally located. Excellent and timely communication."
United States
Mike Shang-Yu
Furnished Apartment Near Longwood
A spacious indoor swimming pool with large windows, modern seating, and a wooden ceiling.

10. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (213 reviews)
"Cozy, comfy and cute✨. Would def rent again❤️"
United States
Erica
The price is NT$5,471
NT$9,985 total
includes taxes & fees
Nov 9 - Nov 10
Global Luxury Suites East Boston
A row of brick buildings with storefronts, including a bakery and a liquor store.

11. 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, (207 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is NT$4,169
NT$7,751 total
includes taxes & fees
Nov 15 - Nov 16
Maverick Suites at 245 Newbury St
A modern hotel room with a bed, a desk, a sofa, and a dining area.

12. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (241 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is NT$6,305
NT$12,795 total
includes taxes & fees
Nov 15 - Nov 16
Charlesgate Suites
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

13. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (368 reviews)
"Great location,"
United States
Rosemary
The price is NT$3,039
NT$5,158 total
includes taxes & fees
Nov 9 - Nov 10
Premier Suites - Bay Village
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

14. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
8.0 out of 10, Very good, (156 reviews)
"Great property in a great location. Tons of food options nearby. Walking distance to Target and Whole Foods. Easy access to the Blue line. The neighborhood was quiet and clean. Boston common is just a block away. Definitely would stay again and highly recommend."
United States
TommyWallace
The price is NT$4,481
NT$8,108 total
includes taxes & fees
Nov 10 - Nov 11
Maverick Suites at 40 Temple St
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

15. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (34 reviews)
"Great location, great Apartment"
United States
Carla Patricia
The price is NT$5,673
NT$10,588 total
includes taxes & fees
Nov 4 - Nov 5
The Concord Hotel
A modern living room with a sofa, a dining table, and a kitchen area with appliances.

16. Luxury 2BR near Cambridge

Luxury 2BR near Cambridge
3.0 star property
Prospect Hill
6.4 out of 10, (5 reviews)
"Was promised a refund of $50 after we spent an entire day without power. Plus VERY hard to communicate with. Would NOT recommend!"
United States
Rebecca
Luxury 2BR near Cambridge
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

17. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (510 reviews)
"Great location, good value and comfortable beds"
United States
Deborah
The price is NT$3,097
NT$5,593 total
includes taxes & fees
Nov 3 - Nov 4
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.

18. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (180 reviews)
"Well located"
United States
Evelyn
The price is NT$3,282
NT$6,731 total
includes taxes & fees
Nov 9 - Nov 10
Maverick Suites at 400 Columbus Ave
Room

19. Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (28 reviews)
"Great location. Exactly as pictured."
United States
Erica
The price is NT$8,139
NT$12,868 total
includes taxes & fees
Nov 15 - Nov 16
Symple Live
A hotel room with a bed, a desk, a lamp, a potted plant, and large windows with blinds.

20. Furnished Apartment near BMC

Furnished Apartment near BMC
3.0 star property
South End
5.6 out of 10, (4 reviews)
"I loved this apartment. It was perfect for what we needed. I only gave four stars because the apartment could use a little love and updating, and that may be important to some people. It was not for me. We were just over 2 miles away from Mass General where my husband was having an operation. It had a full kitchen, 1 1/2 baths, and was surprisingly quiet. The description of the apartment was clear there was no parking space associated with the apartment; however, I found that every night...
United States
Christine
Furnished Apartment near BMC
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

citizenM Boston North Station

citizenM Boston North Station

10/10 Excellent
"I love this hotel. I love the style of the rooms and the environment of the lounge area. My wife and I thoroughly enjoyed our stay. When we were checking out, one of the concierges working the check-in area asked us about our stay, if we had been before, etc. We hadn't purchased a breakfast plan, so she offered us to stay and eat the buffet style breakfast and have coffees on the hotel. The buffet was excellent and the cafe Americano the bartender made for us were perfect. Can't wait to stay at this neat hotel again."
Michael 1-night trip
Posted 4 hours ago
citizenM Boston North Station

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 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.

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. Fenway Park and Encore Boston Harbor 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.