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

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Winchester holiday rentals

Rooftop terrace

1. 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, (649 reviews)
"Best hotel for stay in Boston!"
United States
Frank
The price is Rp5.526.572
Rp6.352.796 total
includes taxes & fees
30 Aug - 31 Aug
Marriott Vacation Club® at Custom House, Boston
Terrace/patio

2. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,236 reviews)
"Dana is a great host, nice spacious rooms"
United States
joseph
The price is Rp2.911.560
Rp3.252.213 total
includes taxes & fees
1 Aug - 2 Aug
Crescent Suites Hotel
Lobby

3. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (298 reviews)
"Amazing location we loved it"
United States
MARLYN
The price is Rp4.700.787
Rp7.273.297 total
includes taxes & fees
2 Aug - 3 Aug
Kasa Boston at Fenway
Exterior

4. 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, (193 reviews)
"Location was perfect! The room was great and exactly what I needed for my business trip"
United States
Michael
The price is Rp3.480.860
Rp5.663.242 total
includes taxes & fees
2 Aug - 3 Aug
Maverick Suites at 245 Newbury St
Apartment | 1 bedroom, desk, laptop workspace, free WiFi

5. Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston
2.5 star property
Everett
8.8 out of 10, Excellent, (19 reviews)
"Good clean property Little out of town with nothing around really Good shower bedroom washing facilities Only slight issue for me was sofa bed not very comfortable and a bit tired But would recommend if that’s your budget range"
United Kingdom
Warren
Furnished Apartments near Encore Boston
Front of property

6. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (400 reviews)
"Easy to move-in, location is good for traveler. The shower room not that clean, some hair from previous guests, just clean it can be manage by guest."
Taiwan
LICHIEH
The price is Rp3.162.775
Rp5.401.478 total
includes taxes & fees
3 Aug - 4 Aug
Maverick Suites at 28 Fenway
Front of property

7. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.8 out of 10, Good, (140 reviews)
"Location Location Location"
United States
Rebecca
The price is Rp2.976.623
Rp5.083.621 total
includes taxes & fees
2 Aug - 3 Aug
Maverick Suites at 40 Temple St
House | 5 bedrooms, desk

8. Enchanting Hidden Door Escape

Enchanting Hidden Door Escape
2.0 star property
Stoneham
The price is Rp8.344.435
Rp16.299.851 total
includes taxes & fees
12 Aug - 13 Aug
Enchanting Hidden Door Escape
Lobby lounge

9. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (728 reviews)
"Great property. Conveniently close to transit, shopping and Boston’s best districts."
United States
Neill
The price is Rp3.205.969
Rp5.858.933 total
includes taxes & fees
16 Aug - 17 Aug
Global Luxury Suites Downtown Boston
42-inch TV with satellite channels

10. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (160 reviews)
"Well located"
United States
Evelyn
The price is Rp2.667.575
Rp4.313.414 total
includes taxes & fees
2 Aug - 3 Aug
Maverick Suites at 400 Columbus Ave
Premium Studio Suite | Premium bedding, desk, iron/ironing board, free WiFi

11. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (219 reviews)
"Very nice room and close to fenway"
United States
timothy
The price is Rp4.355.593
Rp8.123.271 total
includes taxes & fees
2 Aug - 3 Aug
Charlesgate Suites
Studio | Iron/ironing board, free WiFi

12. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.8 out of 10, Good, (6 reviews)
"The room was both well appointed and gorgeous. The location was just what I'd hoped for, enough city energy to feel the vibe but not so much that it lacked peace in the evening. Really cool neighborhood, close to restaurants doing high level cuisine. I had a question for the staff that was answered quickly and received a follow up to double check I had gotten what I needed. This is a spot worth revisiting."
United States
Robert
The price is Rp2.895.295
Rp5.613.383 total
includes taxes & fees
2 Aug - 3 Aug
The Concord Hotel
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets

13. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (426 reviews)
"Great location so close to everything"
United States
Hunter
The price is Rp2.179.604
Rp3.648.074 total
includes taxes & fees
2 Aug - 3 Aug
Temple Place Suites
Premium Apartment | Living area | 24-inch Smart TV with digital channels

14. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (36 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is Rp3.108.556
Rp5.858.526 total
includes taxes & fees
4 Aug - 5 Aug
The Chester Hotel
Luxury Suite 2 | Living area | Smart TV, Netflix, Hulu, streaming services

15. 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 Rp10.663.070
Rp15.373.436 total
includes taxes & fees
5 Aug - 6 Aug
The Monty Boston
Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets

16. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (315 reviews)
"Lovely small property with thoughtful touches like cool water bottles & Nespresso available 24hrs. I had to take a last minute Zoom call and the front desk reserved the business center room for me. The rooms themselves are a bit small but very comfortable beds and linens."
United States
Theresa
The price is Rp2.168.579
Rp3.427.906 total
includes taxes & fees
11 Aug - 12 Aug
Premier Suites - Bay Village
Apartment, 2 Bedrooms | Free WiFi

17. Luxury 2BR near Cambridge

Luxury 2BR near Cambridge
3.0 star property
Prospect Hill
6.8 out of 10, (3 reviews)
"Great apartment but the building's main door was malfunctioning and we could only get in when a resident with a key entered/exited. Also the wifi didn't work. The provider sis not offer any support or compensation, otherwise this would have been a perfect stay."
United States
Yonatan
Luxury 2BR near Cambridge
Interior entrance

18. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (302 reviews)
"Great location super close to great restaurants and shopping. I've stayed at this location a couple of times and it never disappoints!"
United States
Melissa
The price is Rp2.895.295
Rp4.849.047 total
includes taxes & fees
4 Aug - 5 Aug
Maverick Suites at 89 Marion
Apartment, 2 Bedrooms | Interior

19. Furnished Apartment near BMC

Furnished Apartment near BMC
3.0 star property
South End
6.8 out of 10, (3 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
Suite (Luxury 1BR w/ King Bed & City Views) | Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

20. Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (12 reviews)
"Looks like a brand new unit - very tastefully done. Immaculately clean. Stocked with everything you might need. Easy check in and great location - walkable to BU and Fenway."
United States
Kimberley
The price is Rp3.497.125
Rp5.993.561 total
includes taxes & fees
3 Aug - 4 Aug
Symple Live
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
"Je pense qu’il faudrait une autre piscine extérieur. Il y a trop de personnes dans cet hôtel pour contenir seulement une piscine et un spa ."
mirlyne 3-night trip
Posted 1 hour ago
Omni Boston Hotel at the Seaport

Find out more about Winchester

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

  • View our selection of featured holiday rentals in Winchester
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  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

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. 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.