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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Winchester vacation 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, (1,309 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is P9,555
P10,673 total
includes taxes & fees
Oct 31 - Nov 1
Crescent Suites Hotel
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

2. 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, (675 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is P30,917
P35,540 total
includes taxes & fees
Nov 8 - Nov 9
Marriott Vacation Club® at Custom House, Boston
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, (329 reviews)
"Absolutely gorgeous apartments! Concierge was very friendly!"
United States
Kelly
The price is P11,308
P19,497 total
includes taxes & fees
Nov 9 - Nov 10
Kasa Boston at Fenway
A modern living room with a round dining table, grey sofas, and large windows offering city views.

4. Furnished Apts near Harvard Stadium

Furnished Apts near Harvard Stadium
2.0 star property
Allston
8.6 out of 10, Excellent, (17 reviews)
"spacious, clean, central location"
United States
Gregory
The price is P8,085
P17,237 total
includes taxes & fees
Oct 12 - Oct 13
Furnished Apts near Harvard Stadium
A wooden hallway with a patterned floor leading to a door.

5. 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 P6,412
P12,775 total
includes taxes & fees
Nov 9 - Nov 10
Maverick Suites at 89 Marion
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

6. 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 P12,552
P22,372 total
includes taxes & fees
Oct 14 - Oct 15
The Chester Hotel
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

7. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (762 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is P12,009
P21,386 total
includes taxes & fees
Nov 9 - Nov 10
Global Luxury Suites Downtown Boston
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

8. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (442 reviews)
"Great price for the place given the location."
United States
Beenish
The price is P8,424
P15,822 total
includes taxes & fees
Nov 1 - Nov 2
Maverick Suites at 28 Fenway
A hotel room with a large bed, two bedside lamps, a headboard, a wall-mounted abstract art piece, and potted plants.

9. Furnished Apartment Near Longwood

Furnished Apartment Near Longwood
3.0 star property
North Brookline
8.0 out of 10, Very good, (11 reviews)
"Great place, clean, well maintained and centrally located. Excellent and timely communication."
United States
Mike Shang-Yu
The price is P7,056
P16,302 total
includes taxes & fees
Oct 12 - Oct 13
Furnished Apartment Near Longwood
A spacious indoor swimming pool with large windows, modern seating, and a wooden ceiling.

10. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (213 reviews)
"Cozy, comfy and cute✨. Would def rent again❤️"
United States
Erica
The price is P10,686
P19,505 total
includes taxes & fees
Nov 9 - Nov 10
Global Luxury Suites East Boston
A row of brick buildings with storefronts, including a bakery and a liquor store.

11. 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, (207 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is P9,312
P16,481 total
includes taxes & fees
Nov 9 - Nov 10
Maverick Suites at 245 Newbury St
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, (240 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is P11,873
P24,481 total
includes taxes & fees
Oct 12 - Oct 13
Charlesgate 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, (365 reviews)
"Convenient location. Comfortable bed."
United States
Kayla
The price is P6,050
P10,205 total
includes taxes & fees
Nov 9 - Nov 10
Premier Suites - Bay Village
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

14. 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, (156 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 P8,752
P15,838 total
includes taxes & fees
Nov 1 - Nov 2
Maverick Suites at 40 Temple St
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

15. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (33 reviews)
"Great location, great Apartment"
United States
Carla Patricia
The price is P12,325
P22,112 total
includes taxes & fees
Oct 12 - Oct 13
The Concord Hotel
A modern living room with a sofa, a dining table, and a kitchen area with appliances.

16. Luxury 2BR near Cambridge

Luxury 2BR near Cambridge
3.0 star property
Prospect Hill
6.4 out of 10, (5 reviews)
"Was promised a refund of $50 after we spent an entire day without power. Plus VERY hard to communicate with. Would NOT recommend!"
United States
Rebecca
Luxury 2BR near Cambridge
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

17. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (501 reviews)
"Great location, good value and comfortable beds"
United States
Deborah
The price is P6,050
P10,926 total
includes taxes & fees
Nov 2 - Nov 3
Temple Place Suites
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.

18. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (177 reviews)
"Well located"
United States
Evelyn
The price is P6,412
P13,147 total
includes taxes & fees
Nov 9 - Nov 10
Maverick Suites at 400 Columbus Ave
Room

19. Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (28 reviews)
"Great location. Exactly as pictured."
United States
Erica
The price is P17,276
P26,719 total
includes taxes & fees
Nov 9 - Nov 10
Symple Live
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 P10,177
P20,364 total
includes taxes & fees
Oct 12 - Oct 13
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

10/10 Excellent
"Everything was great. The location is excellent, staff was very nice and the rooms are recently renovated and very comfortable and clean. We will stay here again!"
Stephanie 3-night trip
Posted less than an hour ago
The Midtown Hotel MOD Collection by Sonesta

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 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.

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.