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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Winchester vacation rentals

A stone house with a garden bed, a hose, and a brick pathway.

1. 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, (65 reviews)
"Excellent communication with hosts, perfect location for so many sites in the region, lovely space just as advertised. "
United States
Lynn C.
$223 nightly
The price is $249
Aug 30 - Aug 31
Total with taxes and fees
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

2. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (450 reviews)
"Great location so close to everything"
United States
Hunter
$151 nightly
The price is $174
Aug 30 - Aug 31
Total with taxes and fees
Temple Place Suites
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

3. Sleek Studio Apartment in the South End

Sleek Studio Apartment in the South End
Back Bay
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful and clean property, responsive and professional host. I could bring food and cook. I liked my stay. Be aware if you are older or out of shape (me!) be aware that this studio does have stairs. Recommended!"
United States
Paul
$237 nightly
The price is $279
Aug 26 - Aug 27
Total with taxes and fees
Sleek Studio Apartment in the South End
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

4. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (330 reviews)
"Lovely apartment and great stay. Location is very good with lots to do around"
United States
Obianuju
$154 nightly
The price is $177
Aug 27 - Aug 28
Total with taxes and fees
Premier Suites - Bay Village
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

5. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (142 reviews)
"Worth the stay"
Canada
Akansha
$236 nightly
The price is $271
Aug 30 - Aug 31
Total with taxes and fees
Maverick Suites at 40 Temple St
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

6. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,257 reviews)
"The hotel was conveniently located with lots of good dining options nearby. The room was very clean, quiet and comfortable ."
United States
CHRISTINE
$161 nightly
The price is $180
Aug 31 - Sep 1
Total with taxes and fees
Crescent Suites Hotel
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

7. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (37 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
$336 nightly
The price is $386
Aug 26 - Aug 27
Total with taxes and fees
The Chester Hotel
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
8.2 out of 10, Very Good, (200 reviews)
"Great location, really cool place!"
United States
lane
$246 nightly
The price is $283
Aug 31 - Sep 1
Total with taxes and fees
Maverick Suites at 245 Newbury St
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.

9. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.6 out of 10, Exceptional, (40 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
$297 nightly
The price is $342
Aug 28 - Aug 29
Total with taxes and fees
Bright 2BR by Boston Waterfront
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

10. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (410 reviews)
"Easy to move-in, location is good for traveler. The shower room not that clean, some hair from previous guests, just clean it can be manage by guest."
Taiwan
LICHIEH
$236 nightly
The price is $271
Aug 27 - Aug 28
Total with taxes and fees
Maverick Suites at 28 Fenway
A multi-story building with a classic architectural style, featuring a curved facade and numerous windows.

11. Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
Downtown Boston
9.0 out of 10, Wonderful, (2 reviews)
"Host was very communicative. The apartment was very clean and spacious and the location was fantastic! A lot of things in walking distance and train stop nearby for getting to other parts of the city was convenient. I would highly recommend this host and their space! Thank you for your hospitality! Would love to come back."
United States
Rachael M.
$309 nightly
The price is $364
Sep 20 - Sep 21
Total with taxes and fees
Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

12. On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
7.8 out of 10, Good, (52 reviews)
"Very convenient for our stay with a grandson attending Harvard"
United States
Christy
$275 nightly
The price is $315
Aug 26 - Aug 27
Total with taxes and fees
On River/Harvard Sq. two blocks
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

13. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (17 reviews)
"Great room! Cool place to stay. We walked everywhere and stuff was close by. Woud stay here again"
United States
Cotie
$285 nightly
The price is $327
Aug 26 - Aug 27
Total with taxes and fees
The Concord Hotel
A spacious living room with hardwood floors, a sofa, a chair, a coffee table, and a ceiling light fixture.

14. 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, (22 reviews)
"Clean, comfortable and convenient! Communication was detailed, with prompt replies. Everything you need is within 1/2 mile. We enjoyed our stay and will definitely be staying here again. Thanks!!"
United States
Jan L.
$386 nightly
The price is $431
Aug 26 - Aug 27
Total with taxes and fees
Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking
A bedroom with a bed, a ceiling fan, artwork on the wall, and a nightstand with a lamp.

15. Cozy House close to TUFTS, Harvard, MIT 3BR

Cozy House close to TUFTS, Harvard, MIT 3BR
South Medford
9.6 out of 10, Exceptional, (15 reviews)
"Great stay and as advertised. Beds were very comfortable, unit was very clean, and ideal location for visiting Medford area!"
United States
Michael C.
$482 nightly
The price is $523
Aug 26 - Aug 27
Total with taxes and fees
Cozy House close to TUFTS, Harvard, MIT 3BR

16. Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (19 reviews)
"Great location to fenway. Easy and clean."
United States
Allison
$286 nightly
The price is $329
Aug 26 - Aug 27
Total with taxes and fees
Symple Live
A modern kitchen with stainless steel appliances, a blue and white patterned sofa, and a cityscape painting on the wall.

17. Perfetto North End 1brm

Perfetto North End 1brm
North End
9.8 out of 10, Exceptional, (16 reviews)
"Great location- excellent place!"
United States
Deborah S.
$324 nightly
The price is $372
Aug 27 - Aug 28
Total with taxes and fees
Perfetto North End 1brm
A spacious living room with a dining area, wooden columns, and a large window providing natural light.

18. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (320 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
$320 nightly
The price is $357
Sep 2 - Sep 3
Total with taxes and fees
Near Boston Historic two-bedroom with Modern Amenities
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

19. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (658 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
$263 nightly
The price is $302
Aug 30 - Aug 31
Total with taxes and fees
Marriott Vacation Club® at Custom House, Boston
A hotel room with a bed, a nightstand, a lamp, a window with blinds, and a framed picture on the wall.

20. Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!
Downtown Boston
8.4 out of 10, Very Good, (22 reviews)
"Very easy check in, great location to walk to the ballet. Tons of great bars around"
United States
Keith
$220 nightly
The price is $258
Sep 1 - Sep 2
Total with taxes and fees
Perfect One Bedroom Stay In 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.
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Top Winchester Hotel Reviews

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"Nicest hotel on the east coast"
Jonathan 1-night trip
Posted less than an hour ago
Encore Boston Harbor

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 $174 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.

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we have vacation rentals in Winchester close to Griffin Photography Museum, 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?

Boston's Best Vacation Home : This vacation home rental outside of Winchester is equipped with a fireplace, air-conditioning, and laundry facilities to help you feel comfortable during your stay.

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. 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.