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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Winchester holiday rentals

A bedroom with a bed, desk, chair, dresser, and two bedside lamps.

1. Train to Boston! Cozy Apartment in Winchester

Train to Boston! Cozy Apartment in Winchester
3.0 star property
Winchester
10.0 out of 10, Exceptional, (1 review)
"Clean and spacious private entrance mother-in-law suite in a nice and quiet neighborhood. About a 25-40 minute ride, depending on traffic, into Boston."
United States
Selena
Train to Boston! Cozy Apartment in Winchester
A bedroom with a bed, desk, chair, dresser, and two bedside lamps.

2. Train to Boston! Cozy Apartment in Winchester

Train to Boston! Cozy Apartment in Winchester
Winchester
10.0 out of 10, Exceptional, (3 reviews)
"Nice Appartement!Bus round the corner, very quiet!"
United States
Holger V.
Train to Boston! Cozy Apartment in Winchester
A residential house with a covered porch, a garage, and a well-maintained garden.

3. Charming 1-bedroom well located Garden Apartment in Historic West Medford

Charming 1-bedroom well located Garden Apartment in Historic West Medford
West Medford
10.0 out of 10, Exceptional, (16 reviews)
"Will not be disappointed!"
United States
Dave O.
The price is HK$1,172
HK$2,239 total
includes taxes & fees
21 Oct - 22 Oct
Charming 1-bedroom well located Garden Apartment in Historic West Medford
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

4. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,306 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is HK$1,194
HK$1,333 total
includes taxes & fees
31 Oct - 1 Nov
Crescent Suites Hotel
A bedroom with a large bed, a smaller bed, a nightstand with a lamp, a mirror, and a window with a view of greenery.

5. Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston

Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston
Watertown
9.8 out of 10, Exceptional, (65 reviews)
"I was very satisfied with my stay at this property. Mehmet, our host, made sure that we had everything we needed to make our stay comfortable. If I returned to this area, I would definitely stay here again."
United States
Melissa F.
The price is HK$1,012
HK$1,771 total
includes taxes & fees
14 Oct - 15 Oct
Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston
A wooden hallway with a patterned floor leading to a door.

6. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (331 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 HK$871
HK$1,674 total
includes taxes & fees
9 Nov - 10 Nov
Maverick Suites at 89 Marion
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

7. 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, (155 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 HK$1,093
HK$1,979 total
includes taxes & fees
9 Nov - 10 Nov
Maverick Suites at 40 Temple St
A spacious living room with a dining area, wooden columns, and a large window providing natural light.

8. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (332 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
The price is HK$1,962
HK$2,770 total
includes taxes & fees
18 Oct - 19 Oct
Near Boston Historic two-bedroom with Modern Amenities
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, (437 reviews)
"Comfortable room, walkable area, beautiful park across the road, and easy to work with."
United States
Amber
The price is HK$1,052
HK$1,976 total
includes taxes & fees
1 Nov - 2 Nov
Maverick Suites at 28 Fenway
A spacious living room with hardwood floors, a sofa, a chair, a coffee table, and a ceiling light fixture.

10. 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, (25 reviews)
"Can’t thank enough to Jorge and Eduardo for being such great hosts. The apartment is super cozy and close to everything. Quiet neighborhood, good and stores nearby. My kids loved it. About a 9minutes walk to Porter Sqr you can get easily to downtown Boston and its famous Freedom Trail. Supermarkets is about 7 minutes walking. Will definitely book this property again."
United States
Osvaldo
Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking
A dining area with wooden chairs, a table with a patterned tablecloth, and potted plants.

11. 3 bedroom apartment next to T stop / off street parking

3 bedroom apartment next to T stop / off street parking
Charlestown
9.8 out of 10, Exceptional, (71 reviews)
"Excellent location. Host was very responsive. Easy check in. Property was clean and as advertised. Highly recommend."
United States
Teresa M.
The price is HK$1,091
HK$2,400 total
includes taxes & fees
29 Oct - 30 Oct
3 bedroom apartment next to T stop / off street parking
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

12. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (500 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is HK$756
HK$1,365 total
includes taxes & fees
9 Nov - 10 Nov
Temple Place 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, (363 reviews)
"Great spot, Clean, quiet, and convenient. Perfect no frills, no hassle spot in Boston. And very reasonably priced these days!"
United States
Ed
The price is HK$699
HK$1,210 total
includes taxes & fees
9 Nov - 10 Nov
Premier Suites - Bay Village
A hallway with brick walls and a polished floor, leading to a door.

14. Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.0 out of 10, Wonderful, (28 reviews)
"The place was great, and the host was even better! Very good communication and great customer service. I would highly recommend!"
United States
Travis
The price is HK$1,020
HK$1,920 total
includes taxes & fees
2 Nov - 3 Nov
Enjoyable 2-bedroom lower level apartment in charming Lynn
A brick building with a black front door, a staircase, and a well-maintained garden.

15. Free Parking at 1 Bed Basement Apt, Near BU & MIT

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.6 out of 10, Excellent, (37 reviews)
"Friendly hosts"
United States
Jan
The price is HK$746
HK$1,702 total
includes taxes & fees
14 Oct - 15 Oct
Free Parking at 1 Bed Basement Apt, Near BU & MIT
A bedroom with a bed, a chair, a desk, a radiator, and a ceiling fan.

16. Free Parking 2 Bed 1 Bath Steps from BU/Kenmore

Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
Fenway–Kenmore
8.6 out of 10, Excellent, (16 reviews)
"Welcoming host, very responsive"
United States
Matthew G.
The price is HK$1,177
HK$2,805 total
includes taxes & fees
14 Oct - 15 Oct
Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
A marina with boats docked, a red brick building, and modern high-rise apartments in the background.

17. Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Charlestown
9.8 out of 10, Exceptional, (210 reviews)
"Such a quaint and quiet location. We loved staying on the pier. The boat was clean and tidy!! We would definitely stay there again!!"
United States
Angela L.
The price is HK$1,138
HK$4,222 total
includes taxes & fees
2 Nov - 3 Nov
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

18. 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 HK$1,627
HK$2,863 total
includes taxes & fees
14 Oct - 15 Oct
The Chester Hotel
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

19. Stunning Back Bay Studio Apartment

Stunning Back Bay Studio Apartment
Back Bay
8.8 out of 10, Excellent, (19 reviews)
"Cute place with a great location and responsive communication from the host. Would stay here again!"
United States
Lisa
The price is HK$731
HK$1,938 total
includes taxes & fees
4 Nov - 5 Nov
Stunning Back Bay Studio Apartment
A wooden building entrance with two lanterns, a paved path, and a tree with pink leaves in the background.

20. Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#

Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#
Cambridgeport
9.4 out of 10, Exceptional, (44 reviews)
"Very friendly and easy walk to fenway"
United States
thomas p.
The price is HK$1,335
HK$2,642 total
includes taxes & fees
22 Oct - 23 Oct
Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#
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

The Dagny Boston

The Dagny Boston

10/10 Excellent
"Beautiful property in the heart of Boston. Stunning spacious room and amazing coffee/breakfast restaurant."
Jennifer 1-night trip
Posted less than an hour ago
The Dagny 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:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • 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.

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

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots: This holiday home rental outside of Winchester offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with 1 hot tub and a selection of books.

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.