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 Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winchester holiday 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, (1,281 reviews)
The price is S$218
includes taxes & fees
27 Sept - 28 Sept
Crescent Suites Hotel
A wooden hallway with a patterned floor leading to a door.

2. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (315 reviews)
"Room was clean, neat area."
United States
Keir
The price is S$279
includes taxes & fees
29 Sept - 30 Sept
Maverick Suites at 89 Marion
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, (319 reviews)
"Excellent property upscale amenities full kitchen perfect in every way and my room was only a studio I’ll definitely be back next time to try a larger room just to see what they’re like"
United States
Dirk
The price is S$569
includes taxes & fees
19 Oct - 20 Oct
Kasa Boston at Fenway
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

4. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (345 reviews)
"Location is great"
United States
Eria
The price is S$243
includes taxes & fees
28 Sept - 29 Sept
Premier Suites - Bay Village
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

5. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (748 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is S$585
includes taxes & fees
30 Sept - 1 Oct
Global Luxury Suites Downtown Boston
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.

6. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.6 out of 10, Good, (173 reviews)
"Well located"
United States
Evelyn
The price is S$331
includes taxes & fees
30 Sept - 1 Oct
Maverick Suites at 400 Columbus Ave
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, (203 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is S$434
includes taxes & fees
27 Sept - 28 Sept
Maverick Suites at 245 Newbury St
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

8. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (24 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 S$510
includes taxes & fees
30 Sept - 1 Oct
The Concord Hotel
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

9. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (426 reviews)
"Comfortable room, walkable area, beautiful park across the road, and easy to work with."
United States
Amber
The price is S$361
includes taxes & fees
27 Sept - 28 Sept
Maverick Suites at 28 Fenway
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

10. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (479 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is S$272
includes taxes & fees
28 Sept - 29 Sept
Temple Place Suites
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

11. 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, (667 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is S$882
includes taxes & fees
8 Oct - 9 Oct
Marriott Vacation Club® at Custom House, Boston
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, (237 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is S$588
includes taxes & fees
30 Sept - 1 Oct
Charlesgate Suites
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

13. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (148 reviews)
"There only a few things I require from a hotel. Hotel Maverick Suites at 40 are clean, quiet and reasonably priced. I enjoyed my stay there immensely. A bonus was their convenient location."
United States
Jerrold
The price is S$348
includes taxes & fees
27 Sept - 28 Sept
Maverick Suites at 40 Temple St
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

14. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (38 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is S$437
includes taxes & fees
30 Sept - 1 Oct
The Chester Hotel
A hotel room with a large bed, two bedside lamps, a headboard, a wall-mounted abstract art piece, and potted plants.

15. Furnished Apartment Near Longwood

Furnished Apartment Near Longwood
3.0 star property
North Brookline
7.6 out of 10, Good, (7 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 S$484
includes taxes & fees
24 Sept - 25 Sept
Furnished Apartment Near Longwood
A spacious indoor swimming pool with large windows, modern seating, and a wooden ceiling.

16. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (210 reviews)
"Cozy, comfy and cute✨. Would def rent again❤️"
United States
Erica
The price is S$591
includes taxes & fees
30 Sept - 1 Oct
Global Luxury Suites East Boston
A spacious living room with a large window overlooking the sea, a comfortable sofa, a glass coffee table, and a leather armchair.

17. Coastal Charm Lobster Ch Teau

Coastal Charm Lobster Ch Teau
2.0 star property
Swampscott
The price is S$766
includes taxes & fees
28 Sept - 29 Sept
Coastal Charm Lobster Ch Teau
A spacious room with a high ceiling, a large bed, a green dining area, and a view of the outdoors.

18. 1 Mi to Downtown Salem: Studio w/ Fire Pit Access

1 Mi to Downtown Salem: Studio w/ Fire Pit Access
3.0 star property
Salem
9.6 out of 10, Exceptional, (5 reviews)
"Studio was very nicely laid out and the owner of the property was friendly! Area the house was in was quiet but yet still walkable to downtown Salem. Bagel place across the street was amazing as well"
United States
chris
The price is S$519
includes taxes & fees
30 Sept - 1 Oct
1 Mi to Downtown Salem: Studio w/ Fire Pit Access
A modern living room with a round dining table, grey sofas, and large windows offering city views.

19. Furnished Apts near Harvard Stadium

Furnished Apts near Harvard Stadium
2.0 star property
Allston
9.0 out of 10, Wonderful, (15 reviews)
"spacious, clean, central location"
United States
Gregory
Furnished Apts near Harvard Stadium
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
The price is S$712
includes taxes & fees
24 Sept - 25 Sept
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

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

10/10 Excellent
"The best hotel to stay at in the Seaport area! I had a great time walking around seaport and exploring. The staff was extremely kind and helpful. The Bartender"
Nneka 2-night trip
Posted 1 hour ago
Omni Boston Hotel at the Seaport

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.

How many holiday rentals are there in Winchester?

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

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 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.