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.
$228 nightly
The price is $255
Nov 4 - Nov 5
Total with taxes and fees
Charming 1-bedroom well located Garden Apartment in Historic West Medford
A living room with a stone fireplace, a flat-screen TV mounted on the wall, and a shelving unit with baskets and bags.

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.
$222 nightly
The price is $248
Nov 3 - Nov 4
Total with taxes and fees
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, (769 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
$206 nightly
The price is $237
Nov 29 - Nov 30
Total with taxes and fees
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, (1,342 reviews)
"Great place. Friendly staff and comfortable rooms. We always stay at crescent when visiting Boston"
United States
Michael
$139 nightly
The price is $155
Nov 3 - Nov 4
Total with taxes and fees
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.
$305 nightly
The price is $340
Nov 3 - Nov 4
Total with taxes and fees
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.
$568 nightly
The price is $610
Nov 3 - Nov 4
Total with taxes and fees
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, (350 reviews)
"The area was walkable and the room was great!"
United States
Edna
$194 nightly
The price is $217
Dec 1 - Dec 2
Total with taxes and fees
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)
"It was a great location right in a little neighborhood with shops and restaurants. There are two subway stations within a 5 minute walk which made getting to the T very easy. The room was perfect for us!"
United States
David
$240 nightly
The price is $276
Nov 22 - Nov 23
Total with taxes and fees
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, (162 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
$192 nightly
The price is $221
Nov 9 - Nov 10
Total with taxes and fees
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
$270 nightly
The price is $310
Nov 3 - Nov 4
Total with taxes and fees
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.
$277 nightly
The price is $309
Nov 8 - Nov 9
Total with taxes and fees
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, (389 reviews)
"Good place to stay."
United States
Jaetaek
$139 nightly
The price is $160
Nov 9 - Nov 10
Total with taxes and fees
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.
$201 nightly
The price is $225
Nov 8 - Nov 9
Total with taxes and fees
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, (345 reviews)
"Great location, very comfortable apartment, great facilities, everyone was friendly and helpful!!!"
United States
antonio
$270 nightly
The price is $297
Nov 9 - Nov 10
Total with taxes and fees
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, (470 reviews)
"Great location!"
United States
Mario Quezada
$199 nightly
The price is $229
Dec 1 - Dec 2
Total with taxes and fees
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
$259 nightly
The price is $298
Nov 9 - Nov 10
Total with taxes and fees
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, (37 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
$257 nightly
The price is $296
Nov 8 - Nov 9
Total with taxes and fees
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, (119 reviews)
"The houseboat was great! Everyone was super friendly and helpful. Can’t wait for our next stay!"
United States
Frank M.
$406 nightly
The price is $466
Nov 30 - Dec 1
Total with taxes and fees
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
$217 nightly
The price is $255
Nov 9 - Nov 10
Total with taxes and fees
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.
$383 nightly
The price is $428
Nov 8 - Nov 9
Total with taxes and fees
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

Wyndham Boston Beacon Hill

Wyndham Boston Beacon Hill

10/10 Excellent
"Great location. And easy access parking."
Donald 3-night trip
Posted 1 hour ago
Wyndham Boston Beacon Hill

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 $155 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 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.