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

Our top choices for Winchester holiday rentals

Property grounds

1. Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.

Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
Medford
10.0 out of 10, Exceptional, (65 reviews)
"Excellent communication with hosts, perfect location for so many sites in the region, lovely space just as advertised. "
United States
Lynn C.
The price is HK$916
HK$2,013 total
includes taxes & fees
30 Aug - 31 Aug
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
Room

2. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (449 reviews)
"Great location so close to everything"
United States
Hunter
The price is HK$762
HK$1,372 total
includes taxes & fees
25 Aug - 26 Aug
Temple Place Suites
Exterior

3. Sleek Studio Apartment in the South End

Sleek Studio Apartment in the South End
Back Bay
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful and clean property, responsive and professional host. I could bring food and cook. I liked my stay. Be aware if you are older or out of shape (me!) be aware that this studio does have stairs. Recommended!"
United States
Paul
The price is HK$737
HK$1,945 total
includes taxes & fees
25 Aug - 26 Aug
Sleek Studio Apartment in the South End
Room

4. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (330 reviews)
"Lovely apartment and great stay. Location is very good with lots to do around"
United States
Obianuju
The price is HK$769
HK$1,290 total
includes taxes & fees
25 Aug - 26 Aug
Premier Suites - Bay Village
Front of property

5. 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 HK$1,101
HK$1,986 total
includes taxes & fees
26 Aug - 27 Aug
Maverick Suites at 40 Temple St
Terrace/patio

6. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,257 reviews)
"Great location if spending time in Waltham. Walking distance to every thing"
United States
Rob
The price is HK$1,263
HK$1,411 total
includes taxes & fees
28 Aug - 29 Aug
Crescent Suites Hotel
Living area

7. 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 HK$1,362
HK$2,557 total
includes taxes & fees
8 Sept - 9 Sept
The Chester Hotel
Exterior

8. 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, (200 reviews)
"Great location, really cool place!"
United States
lane
The price is HK$1,171
HK$2,067 total
includes taxes & fees
31 Aug - 1 Sept
Maverick Suites at 245 Newbury St
Living area

9. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.6 out of 10, Exceptional, (40 reviews)
"7 min from the airport, seamless check in and entry and a spotless, welcoming place- with coffee! Great rental- perfect if you’re coming/going from Logan"
United States
Bridget
The price is HK$720
HK$2,341 total
includes taxes & fees
26 Aug - 27 Aug
Bright 2BR by Boston Waterfront
Front of property

10. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (410 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 HK$1,184
HK$2,127 total
includes taxes & fees
25 Aug - 26 Aug
Maverick Suites at 28 Fenway
Exterior

11. Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
Downtown Boston
9.0 out of 10, Wonderful, (2 reviews)
"Host was very communicative. The apartment was very clean and spacious and the location was fantastic! A lot of things in walking distance and train stop nearby for getting to other parts of the city was convenient. I would highly recommend this host and their space! Thank you for your hospitality! Would love to come back."
United States
Rachael M.
The price is HK$991
HK$2,437 total
includes taxes & fees
25 Aug - 26 Aug
Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
Living area

12. On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
7.8 out of 10, Good, (52 reviews)
"Very convenient for our stay with a grandson attending Harvard"
United States
Christy
The price is HK$1,334
HK$2,469 total
includes taxes & fees
25 Aug - 26 Aug
On River/Harvard Sq. two blocks
Room

13. 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 HK$1,298
HK$2,484 total
includes taxes & fees
25 Aug - 26 Aug
The Concord Hotel
Living area

14. Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking

Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking
Ward Two
10.0 out of 10, Exceptional, (22 reviews)
"Clean, comfortable and convenient! Communication was detailed, with prompt replies. Everything you need is within 1/2 mile. We enjoyed our stay and will definitely be staying here again. Thanks!!"
United States
Jan L.
The price is HK$1,392
HK$3,131 total
includes taxes & fees
26 Aug - 27 Aug
Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking
Room

15. Cozy House close to TUFTS, Harvard, MIT 3BR

Cozy House close to TUFTS, Harvard, MIT 3BR
South Medford
9.6 out of 10, Exceptional, (15 reviews)
"Great stay and as advertised. Beds were very comfortable, unit was very clean, and ideal location for visiting Medford area!"
United States
Michael C.
The price is HK$1,544
HK$4,098 total
includes taxes & fees
25 Aug - 26 Aug
Cozy House close to TUFTS, Harvard, MIT 3BR
Room

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 HK$1,499
HK$2,579 total
includes taxes & fees
26 Aug - 27 Aug
Symple Live
Interior

17. Perfetto North End 1brm

Perfetto North End 1brm
North End
9.8 out of 10, Exceptional, (16 reviews)
"Great location- excellent place!"
United States
Deborah S.
The price is HK$1,333
HK$3,037 total
includes taxes & fees
27 Aug - 28 Aug
Perfetto North End 1brm
Interior

18. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (320 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
The price is HK$1,960
HK$2,802 total
includes taxes & fees
2 Sept - 3 Sept
Near Boston Historic two-bedroom with Modern Amenities
Rooftop terrace

19. 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, (658 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is HK$2,526
HK$2,903 total
includes taxes & fees
2 Sept - 3 Sept
Marriott Vacation Club® at Custom House, Boston
Room

20. Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!
Downtown Boston
8.4 out of 10, Very good, (22 reviews)
"Very easy check in, great location to walk to the ballet. Tons of great bars around"
United States
Keith
The price is HK$1,098
HK$2,090 total
includes taxes & fees
1 Sept - 2 Sept
Perfect One Bedroom Stay In Downtown Boston!
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

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

10/10 Excellent
"Great staff. Early check in and late check out was helpful"
Mark 3-night trip
Posted less than an hour ago
Hyatt Regency Boston/Cambridge

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 holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Griffin Photography Museum, 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.

What are some of the best holiday rentals that Winchester has to offer?

Boston's Best Vacation Home : This holiday home rental outside of Winchester is equipped with a fireplace, air conditioning and laundry facilities to help you feel comfortable during your stay.

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.