Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Winchester

Desk, laptop workspace, free WiFi, bed sheets
Bay Village Suites

Aparthotel in Bay Village

2.0 star property
6.4 out of 10, (249)
"Great location nice neighborhood "
United States
Jose
$131 nightly
The price is $151
Dec 5 - Dec 6
Total with taxes and fees
Bay Village Suites
Iron/ironing board, free WiFi, bed sheets
Premier Suites - Bay Village

Aparthotel in Bay Village

2.0 star property
6.4 out of 10, (251)
"Clean room, good location, check in check out easily!"
United States
HIEN T
$114 nightly
The price is $131
Dec 7 - Dec 8
Total with taxes and fees
Premier Suites - Bay Village
Lobby lounge
Global Luxury Suites Downtown Boston

Aparthotel in Chinatown

4.0 star property
8.0 out of 10, Very Good, (626)
"This unit and location was perfect for my trip! Super close to many of the attractions that we wanted to visit. "
United States
Lily
$140 nightly
The price is $160
Dec 15 - Dec 16
Total with taxes and fees
Global Luxury Suites Downtown Boston
Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets
Temple Place Suites

Apartment in Downtown Boston

2.5 star property
7.0 out of 10, Good, (322)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
$141 nightly
The price is $162
Dec 5 - Dec 6
Total with taxes and fees
Temple Place Suites
Exterior
Maverick Suites at 245 Newbury St

Aparthotel in Back Bay

2.0 star property
8.2 out of 10, Very Good, (154)
"Room was clean and a good size. Location was perfect - walking distance to where I needed to be. "
United States
Steven
$197 nightly
The price is $226
Dec 10 - Dec 11
Total with taxes and fees
Maverick Suites at 245 Newbury St
Front of property
Maverick Suites at 40 Temple St

Aparthotel in Beacon Hill

2.0 star property
7.6 out of 10, Good, (102)
"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"
United Kingdom
Jordan Elizabeth Marie
$199 nightly
The price is $229
Dec 7 - Dec 8
Total with taxes and fees
Maverick Suites at 40 Temple St
42-inch TV with satellite channels
Maverick Suites at 400 Columbus Ave

Aparthotel in South End

2.0 star property
7.2 out of 10, Good, (132)
"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
$172 nightly
The price is $198
Jan 4 - Jan 5, 2026
Total with taxes and fees
Maverick Suites at 400 Columbus Ave
Deluxe Studio Suite (2nd Floor - Unit 202) | Individually furnished, iron/ironing board, free WiFi, bed sheets
Maverick Suites at 28 Fenway

Apartment in Fenway–Kenmore

3.0 star property
8.8 out of 10, Excellent, (322)
"Spotless room, spotless building, great staff, comfortable bed. "
United States
Patricia
$190 nightly
The price is $218
Dec 7 - Dec 8
Total with taxes and fees
Maverick Suites at 28 Fenway
Interior entrance
Maverick Suites at 89 Marion

Aparthotel in Coolidge Corner South Side

2.0 star property
8.2 out of 10, Very Good, (270)
"Had an amazing time. Loved the property and it's location in proximity to entertainment, transportation, dining and scenic entertainment. "
United States
Nicole
$184 nightly
The price is $206
Jan 4 - Jan 5, 2026
Total with taxes and fees
Maverick Suites at 89 Marion
Property grounds
Crescent Suites Hotel

Aparthotel in South Side

3.0 star property
9.6 out of 10, Exceptional, (1141)
"Lovely, quiet place."
United States
Fatu
$137 nightly
The price is $154
Dec 30 - Dec 31
Total with taxes and fees
Crescent Suites Hotel
TV, offices
Come Visit Boston and Stay In Our Homey Studio

Apartment in Downtown Boston

8.8 out of 10, Excellent, (3)
"Great central location! Tiny but super !would come back . Great food , bars, brewery , breakfast at our doorstep. By the park too!"
United States
Dean and Courtenay M.
$183 nightly
The price is $215
Dec 7 - Dec 8
Total with taxes and fees
Come Visit Boston and Stay In Our Homey Studio
Luxury Suite 2 | Living area | Smart TV, Netflix, Hulu, streaming services
The Monty Boston

Aparthotel in Downtown Boston

2.5 star property
9.4 out of 10, Exceptional, (28)
"Amazing property, would stay again."
United States
Doug
$590 nightly
The price is $678
Dec 5 - Dec 6
Total with taxes and fees
The Monty Boston
Apartment, 2 Bedrooms | Private kitchen | Mini-fridge, microwave, cookware/dishes/utensils, paper towels
Maverick Suites at 402 Columbus Ave

Aparthotel in South End

2.5 star property
8.0 out of 10, Very Good, (67)
"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
$193 nightly
The price is $222
Dec 7 - Dec 8
Total with taxes and fees
Maverick Suites at 402 Columbus Ave
1 bedroom, desk, WiFi, bed sheets
The Chester: Penthouse One Bedroom

Apartment in South End

2.0 star property
10.0 out of 10, Exceptional, (2)
"Absolutely loved my stay. Great location, beautiful place. Clean and bright. We will be back!"
United States
Linda C.
$369 nightly
The price is $424
Dec 21 - Dec 22
Total with taxes and fees
The Chester: Penthouse One Bedroom
Exterior
North End Gem ★ Prime Location + Parking Included

Apartment in North End

9.6 out of 10, Exceptional, (58)
"Had a very nice time close to everything walking distance to alot of fun and exciting things "
United States
Lynn W.
$287 nightly
The price is $306
Dec 5 - Dec 6
Total with taxes and fees
North End Gem ★ Prime Location + Parking Included
Apartment | Premium bedding, desk, iron/ironing board, free WiFi
Charlesgate Suites

Aparthotel in Fenway–Kenmore

3.5 star property
9.4 out of 10, Exceptional, (201)
"New spot for us in South Bay. Convenient and easy with easy walk to Commonwealth and restaurants of Newbury"
United States
Brian
$382 nightly
The price is $439
Dec 14 - Dec 15
Total with taxes and fees
Charlesgate Suites
City Studio | Egyptian cotton sheets, premium bedding, memory foam beds
The Chester Hotel

Aparthotel in South End

4.0 star property
8.6 out of 10, Excellent, (27)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
$382 nightly
The price is $440
Dec 7 - Dec 8
Total with taxes and fees
The Chester Hotel
Private kitchen
Perfetto North End 1brm

Apartment in North End

10.0 out of 10, Exceptional, (11)
"The location was perfect - we would stay here again.The description and pictures are accurate."
United States
Kenna E.
$291 nightly
The price is $335
Dec 7 - Dec 8
Total with taxes and fees
Perfetto North End 1brm
1 bedroom, WiFi
Modern North End Studio

Apartment in North End

9.0 out of 10, Wonderful, (10)
"Convenient location. Great restaurants. Perfect apatment for a couple. "
United States
Holly V.
$270 nightly
The price is $310
Dec 9 - Dec 10
Total with taxes and fees
Modern North End Studio
1 bedroom, desk, iron/ironing board, WiFi
Studio Awaits Your Next Stay!

Apartment in Bay Village

10.0 out of 10, Exceptional, (4)
"Would stay again"
United States
mark p.
$183 nightly
The price is $215
Dec 16 - Dec 17
Total with taxes and fees
Studio Awaits Your Next Stay!
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

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

10/10 Excellent
"Staff was very friendly and helpful. Rooms were clean and new. "
Rosemarie 3-night trip
Posted 2 days ago
Omni Boston Hotel at the Seaport

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $131 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Cozy Salem Getaway. Historic Home Near All the Sights: This vacation home rental outside of Winchester offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 Harvard Square 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.