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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Winchester vacation rentals

A residential house with a covered porch, a garage, and a well-maintained garden.

1. 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, (18 reviews)
"Great stay and great host! Would come back! Area is super safe and lovely!"
United States
I A.
The price is ￥21,315
￥39,858 total
includes taxes & fees
Nov 5 - Nov 6
Charming 1-bedroom well located Garden Apartment in Historic West Medford
A stone house with a garden bed, a hose, and a brick pathway.

2. 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, (68 reviews)
"Excellent place to stay in Medford. Everything was great and we ended up only had two persons staying here, for which it was great!"
United States
Michael C.
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

3. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (772 reviews)
"Great room: new and spacious. The kitchenette has everything i needed and more."
United States
Yelitza
The price is ￥15,286
￥36,179 total
includes taxes & fees
Nov 22 - Nov 23
Global Luxury Suites Downtown Boston
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, (1,345 reviews)
"Great place. Friendly staff and comfortable rooms. We always stay at crescent when visiting Boston"
United States
Michael
The price is ￥22,094
￥24,679 total
includes taxes & fees
Nov 10 - Nov 11
Crescent Suites Hotel
A spacious living room with hardwood floors, a sofa, a chair, a coffee table, and a ceiling light fixture.

5. 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)
"Great place close to places of interest. Walking distance to Dali - a Spanish Tapas restaurant that is authentic and delicious. Enjoyed our stay."
United States
Mike M.
The price is ￥27,217
￥56,502 total
includes taxes & fees
Nov 8 - Nov 9
Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking
A modern living room with a sectional sofa, a wooden coffee table, and a fireplace.

6. Enchanting Hidden Door Escape

Enchanting Hidden Door Escape
Stoneham
9.6 out of 10, Exceptional, (37 reviews)
"Everything was wonderful . The only suggestion would be to have a couple larger pans for cooking "
United States
John D.
The price is ￥39,220
￥95,407 total
includes taxes & fees
Nov 8 - Nov 9
Enchanting Hidden Door Escape
A wooden hallway with a patterned floor leading to a door.

7. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (353 reviews)
"The area was walkable and the room was great!"
United States
Edna
The price is ￥16,199
￥32,204 total
includes taxes & fees
Dec 1 - Dec 2
Maverick Suites at 89 Marion
A row of brick buildings with storefronts, including a bakery and a liquor store.

8. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.4 out of 10, Very good, (216 reviews)
"Great location - plenty to do."
United States
Chloe
The price is ￥22,736
￥40,654 total
includes taxes & fees
Nov 22 - Nov 23
Maverick Suites at 245 Newbury St
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

9. 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, (164 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 ￥15,916
￥32,814 total
includes taxes & fees
Nov 9 - Nov 10
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.

10. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (42 reviews)
"Charming historic building with modern room interiors and amenities, high quality linens/towels, and an easy walk to BSO, Northeastern University, and shopping."
United States
Andrew
The price is ￥22,736
￥46,100 total
includes taxes & fees
Nov 10 - Nov 11
The Chester Hotel
A spacious living room with a dining area, wooden columns, and a large window providing natural light.

11. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (337 reviews)
"This property is gorgeous! No need for anything once you arrive because it has everything!! The owner is great at communicating and accommodating. If you are in the Boston area and want a comfortable, safe and lovely place to stay this is it. Can’t wait to visit again!"
United States
Lesley M.
The price is ￥35,525
￥48,852 total
includes taxes & fees
Nov 9 - Nov 10
Near Boston Historic two-bedroom with Modern Amenities
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

12. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (394 reviews)
"Good place to stay."
United States
Jaetaek
The price is ￥13,357
￥23,524 total
includes taxes & fees
Nov 11 - Nov 12
Premier Suites - Bay Village
A bedroom with a large bed, a smaller bed, a nightstand with a lamp, a mirror, and a window with a view of greenery.

13. 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 ￥21,315
￥35,449 total
includes taxes & fees
Nov 9 - Nov 10
Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

14. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (347 reviews)
"Great location, very comfortable apartment, great facilities, everyone was friendly and helpful!!!"
United States
antonio
The price is ￥28,420
￥46,880 total
includes taxes & fees
Nov 9 - Nov 10
Kasa Boston at Fenway
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

15. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (473 reviews)
"Great location and the room was nicely decorated and clean!"
United States
Judy
The price is ￥16,199
￥34,049 total
includes taxes & fees
Dec 1 - Dec 2
Maverick Suites at 28 Fenway
A living room with a grey sofa, a black armchair, a coffee table, and a blue rug. There are two windows with blinds, a bookshelf, and a potted plant.

16. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.6 out of 10, Exceptional, (51 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 ￥15,154
￥45,551 total
includes taxes & fees
Nov 9 - Nov 10
Bright 2BR by Boston Waterfront
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

17. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (38 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
The price is ￥25,294
￥49,040 total
includes taxes & fees
Nov 9 - Nov 10
The Concord Hotel
A room with a large window overlooking a marina with boats and buildings.

18. Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (120 reviews)
"The houseboat was great! Everyone was super friendly and helpful. Can’t wait for our next stay!"
United States
Frank M.
The price is ￥21,749
￥76,545 total
includes taxes & fees
Nov 5 - Nov 6
Fun houseboat. Walk to Boston attractions WIFI
A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a large window providing natural light.

19. Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
9.0 out of 10, Wonderful, (2 reviews)
"Was an amazing stay!"
United States
mariia
The price is ￥15,000
￥40,518 total
includes taxes & fees
Nov 9 - Nov 10
Beautiful 1BR near Fenway Park + Kenmore!
A modern kitchen with dark cabinets, a white countertop, stainless steel appliances, and a central island with bar stools.

20. 3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces

3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
East Somerville
10.0 out of 10, Exceptional, (31 reviews)
"Beautiful unit with attentive host and safe parking. We enjoyed our stay."
United States
Debbie L.
The price is ￥18,489
￥60,335 total
includes taxes & fees
Nov 8 - Nov 9
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
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

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"Despite the strike outdoors, the stay was lovely!"
Makesha 2-night trip
Posted 1 hour ago
Encore Boston Harbor

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

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.

What are some of the best vacation home rentals in Winchester?

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots: This vacation 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a hot tub and a selection of books.

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.