Winchester Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    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

Tonight
Oct 25 - Oct 26
Tomorrow
Oct 26 - Oct 27
Next weekend
Oct 31 - Nov 2
In two weeks
Nov 7 - Nov 9

Vacation Rentals in Winchester

Lobby lounge
Global Luxury Suites Downtown Boston
Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very Good, (615)
"This unit and location was perfect for my trip! Super close to many of the attractions that we wanted to visit. "
United States
Lily
Global Luxury Suites Downtown Boston
42-inch TV with satellite channels
Maverick Suites at 400 Columbus Ave
Maverick Suites at 400 Columbus Ave
2.0 star property
7.2 out of 10, Good, (126)
"I thoroughly enjoyed my stay. Great property in a nice neighborhood in Back Bay. Bonus: it's also near the Logan Express bus stop for easy airport access. "
United States
Mark
The price is ￥14,033
￥30,187 total
includes taxes & fees
Nov 25 - Nov 26
Maverick Suites at 400 Columbus Ave
Individually furnished, laptop workspace, iron/ironing board, bed sheets
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
4.0 star property
9.2 out of 10, Wonderful, (944)
"The property was awesome, well located, not far to jump on trains etc Close to MGM musical hall, which was the reason for our trip. Would 100% recommend this property if your looking for a nice peaceful area but close enough to all the popular touristy areas. Loved our stay, thank you "
United Kingdom
Lyndsey
The price is ￥26,001
￥30,668 total
includes taxes & fees
Nov 9 - Nov 10
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
Deluxe Studio Suite (2nd Floor - Unit 202) | 1 bedroom, individually furnished, iron/ironing board, free WiFi
Maverick Suites at 28 Fenway
Maverick Suites at 28 Fenway
3.0 star property
8.8 out of 10, Excellent, (303)
"great location"
United States
Mario
The price is ￥14,812
￥31,961 total
includes taxes & fees
Nov 25 - Nov 26
Maverick Suites at 28 Fenway
Front of property
Maverick Suites at 40 Temple St
Maverick Suites at 40 Temple St
2.0 star property
7.4 out of 10, Good, (100)
"Great location "
Canada
James
The price is ￥20,233
￥37,289 total
includes taxes & fees
Nov 19 - Nov 20
Maverick Suites at 40 Temple St
Exterior
Maverick Suites at 245 Newbury St
Maverick Suites at 245 Newbury St
2.0 star property
8.2 out of 10, Very Good, (150)
"Clean. Bed super comfortable, easy walk to Fenway, restaurants, subway, shops, library"
United States
Elizabeth rising
The price is ￥21,790
￥39,080 total
includes taxes & fees
Nov 19 - Nov 20
Maverick Suites at 245 Newbury St
Desk, laptop workspace, free WiFi, bed sheets
Bay Village Suites
Bay Village Suites
2.0 star property
6.4 out of 10, (235)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites
Apartment | 1 bedroom, premium bedding, desk, iron/ironing board
Charlesgate Suites
Charlesgate Suites
3.5 star property
9.4 out of 10, Exceptional, (194)
"New spot for us in South Bay. Convenient and easy with easy walk to Commonwealth and restaurants of Newbury"
United States
Brian
The price is ￥31,739
￥62,796 total
includes taxes & fees
Nov 10 - Nov 11
Charlesgate Suites
Iron/ironing board, free WiFi, bed sheets
Premier Suites - Bay Village
Premier Suites - Bay Village
2.0 star property
6.4 out of 10, (237)
"Clean room, good location, check in check out easily!"
United States
HIEN T
The price is ￥30,213
￥42,622 total
includes taxes & fees
Oct 26 - Oct 27
Premier Suites - Bay Village
Deluxe Studio | 1 bedroom, desk, iron/ironing board, free WiFi
Temple Place Suites
Temple Place Suites
2.5 star property
7.0 out of 10, Good, (298)
"Very convenient place to stay, near transportation and waking distance to historic points and shopping. "
United States
Carolina
The price is ￥14,583
￥26,426 total
includes taxes & fees
Nov 16 - Nov 17
Temple Place Suites
Exterior
Best Location Studio In Downtown Boston
Best Location Studio In Downtown Boston
10.0 out of 10, Exceptional, (1)
"In town to celebrate a special event."
United States
Pam P.
The price is ￥21,248
￥38,822 total
includes taxes & fees
Nov 17 - Nov 18
Best Location Studio In Downtown Boston
Apartment, 2 Bedrooms | Private kitchen | Mini-fridge, microwave, cookware/dishes/utensils, paper towels
Maverick Suites at 402 Columbus Ave
Maverick Suites at 402 Columbus Ave
2.5 star property
8.0 out of 10, Very Good, (65)
"Loved how cozy and clean it was. Location was great, near many points of interest. Parking at an extra fee, but plenty of street parking in the area. "
United States
Isaiah Joel Santa
The price is ￥14,033
￥30,187 total
includes taxes & fees
Nov 25 - Nov 26
Maverick Suites at 402 Columbus Ave
Property amenity
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
4.0 star property
8.8 out of 10, Excellent, (273)
"Check in staff was amazing! Love the apartment and location!"
United States
Tina
The price is ￥28,702
￥33,855 total
includes taxes & fees
Nov 10 - Nov 11
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
1 bedroom, WiFi
Modern North End Studio
Modern North End Studio
9.4 out of 10, Exceptional, (8)
"Really cute, clean, and awesome location!"
United States
Carrie T.
The price is ￥25,177
￥56,128 total
includes taxes & fees
Nov 11 - Nov 12
Modern North End Studio
Interior entrance
Maverick Suites at 89 Marion
Maverick Suites at 89 Marion
2.0 star property
8.4 out of 10, Very Good, (261)
"Had an amazing time. Loved the property and it's location in proximity to entertainment, transportation, dining and scenic entertainment. "
United States
Nicole
The price is ￥17,021
￥32,673 total
includes taxes & fees
Nov 24 - Nov 25
Maverick Suites at 89 Marion
Interior
Ideal North End 1brm Central To Everything
Ideal North End 1brm Central To Everything
9.6 out of 10, Exceptional, (36)
"We had a very nice stay. Such a great location! Walkable to tons of restaurants and right near the Paul Revere statue and Old North Church!"
United States
Sean R.
The price is ￥22,126
￥54,200 total
includes taxes & fees
Nov 17 - Nov 18
Ideal North End 1brm Central To Everything
Property grounds
Crescent Suites Hotel
Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (1114)
"The staff were friendly and the accommodation was good"
United States
Sudha
Crescent Suites Hotel
Exterior
*Ghostly 2BR Halloween Home|Salem+Beverly|Parking
*Ghostly 2BR Halloween Home|Salem+Beverly|Parking
10.0 out of 10, Exceptional, (30)
"Cozy and convenient to everything. "
United States
Christopher M.
The price is ￥18,343
￥47,810 total
includes taxes & fees
Nov 23 - Nov 24
*Ghostly 2BR Halloween Home|Salem+Beverly|Parking
City Studio | 1 bedroom, Egyptian cotton sheets, premium bedding, memory foam beds
The Chester Hotel
The Chester Hotel
4.0 star property
8.4 out of 10, Very Good, (25)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
The price is ￥27,192
￥58,443 total
includes taxes & fees
Nov 10 - Nov 11
The Chester Hotel
Smart TV, books
King Bed Loft in the Heart of Downtown Boston
King Bed Loft in the Heart of Downtown Boston
10.0 out of 10, Exceptional, (35)
"It was my first time staying here, and the room was very clean and fresh. The staff were extremely friendly and helpful, and the facilities were perfect. I will definitely stay here again, and I highly recommend it to anyone."
Japan
MINEKI
The price is ￥23,250
￥52,558 total
includes taxes & fees
Nov 23 - Nov 24
King Bed Loft in the Heart of 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.
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 Arcadian Hotel

The Arcadian Hotel

10/10 Excellent
"The breakfast buffet was picked over and not much left at 9:00 am. No bananas, no pastery."
David 1-night trip
Posted 15 hours ago
The Arcadian Hotel

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.

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

Casa Castor • Private Room 1: This vacation home rental outside of Winchester has air-conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge to make your meal-planning easier.

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 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.