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
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

A bedroom with a bed, desk, chair, dresser, and two bedside lamps.

1. Train to Boston! Cozy Apartment in Winchester

Train to Boston! Cozy Apartment in Winchester
3.0 star property
Winchester
10.0 out of 10, Exceptional, (1 review)
"Clean and spacious private entrance mother-in-law suite in a nice and quiet neighborhood. About a 25-40 minute ride, depending on traffic, into Boston."
United States
Selena
Train to Boston! Cozy Apartment in Winchester
A bedroom with a bed, desk, chair, dresser, and two bedside lamps.

2. Train to Boston! Cozy Apartment in Winchester

Train to Boston! Cozy Apartment in Winchester
Winchester
10.0 out of 10, Exceptional, (3 reviews)
"Nice Appartement!Bus round the corner, very quiet!"
United States
Holger V.
Train to Boston! Cozy Apartment in Winchester
A residential house with a covered porch, a garage, and a well-maintained garden.

3. 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, (16 reviews)
"Will not be disappointed!"
United States
Dave O.
$257 nightly
The price is $287
Nov 1 - Nov 2
Total with taxes and fees
Charming 1-bedroom well located Garden Apartment in Historic West Medford
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, (1,309 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
$140 nightly
The price is $157
Nov 2 - Nov 3
Total with taxes and fees
Crescent Suites Hotel
A bedroom with a large bed, a smaller bed, a nightstand with a lamp, a mirror, and a window with a view of greenery.

5. 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.
$205 nightly
The price is $229
Oct 14 - Oct 15
Total with taxes and fees
Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston
A wooden hallway with a patterned floor leading to a door.

6. 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
$206 nightly
The price is $230
Nov 9 - Nov 10
Total with taxes and fees
Maverick Suites at 89 Marion
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

7. 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
$252 nightly
The price is $290
Nov 1 - Nov 2
Total with taxes and fees
Maverick Suites at 40 Temple St
A spacious living room with a dining area, wooden columns, and a large window providing natural light.

8. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (333 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
$320 nightly
The price is $357
Oct 25 - Oct 26
Total with taxes and fees
Near Boston Historic two-bedroom with Modern Amenities
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

9. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (440 reviews)
"Great price for the place given the location."
United States
Beenish
$234 nightly
The price is $269
Nov 1 - Nov 2
Total with taxes and fees
Maverick Suites at 28 Fenway
A spacious living room with hardwood floors, a sofa, a chair, a coffee table, and a ceiling light fixture.

10. 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)
"Can’t thank enough to Jorge and Eduardo for being such great hosts. The apartment is super cozy and close to everything. Quiet neighborhood, good and stores nearby. My kids loved it. About a 9minutes walk to Porter Sqr you can get easily to downtown Boston and its famous Freedom Trail. Supermarkets is about 7 minutes walking. Will definitely book this property again."
United States
Osvaldo
Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking
A dining area with wooden chairs, a table with a patterned tablecloth, and potted plants.

11. 3 bedroom apartment next to T stop / off street parking

3 bedroom apartment next to T stop / off street parking
Charlestown
9.8 out of 10, Exceptional, (71 reviews)
"Excellent location. Host was very responsive. Easy check in. Property was clean and as advertised. Highly recommend."
United States
Teresa M.
$306 nightly
The price is $352
Nov 8 - Nov 9
Total with taxes and fees
3 bedroom apartment next to T stop / off street parking
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

12. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (500 reviews)
"Great location, good value and comfortable beds"
United States
Deborah
$162 nightly
The price is $186
Nov 2 - Nov 3
Total with taxes and fees
Temple Place 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, (364 reviews)
"Convenient location. Comfortable bed."
United States
Kayla
$152 nightly
The price is $175
Nov 9 - Nov 10
Total with taxes and fees
Premier Suites - Bay Village
A hallway with brick walls and a polished floor, leading to a door.

14. Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.0 out of 10, Wonderful, (28 reviews)
"The place was great, and the host was even better! Very good communication and great customer service. I would highly recommend!"
United States
Travis
$223 nightly
The price is $245
Nov 2 - Nov 3
Total with taxes and fees
Enjoyable 2-bedroom lower level apartment in charming Lynn
A brick building with a black front door, a staircase, and a well-maintained garden.

15. Free Parking at 1 Bed Basement Apt, Near BU & MIT

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.6 out of 10, Excellent, (37 reviews)
"Friendly hosts"
United States
Jan
$200 nightly
The price is $218
Oct 14 - Oct 15
Total with taxes and fees
Free Parking at 1 Bed Basement Apt, Near BU & MIT
A bedroom with a bed, a chair, a desk, a radiator, and a ceiling fan.

16. Free Parking 2 Bed 1 Bath Steps from BU/Kenmore

Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
Fenway–Kenmore
8.6 out of 10, Excellent, (17 reviews)
"Welcoming host, very responsive"
United States
Matthew G.
$283 nightly
The price is $324
Oct 14 - Oct 15
Total with taxes and fees
Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
A marina with boats docked, a red brick building, and modern high-rise apartments in the background.

17. Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Charlestown
9.8 out of 10, Exceptional, (210 reviews)
"Such a quaint and quiet location. We loved staying on the pier. The boat was clean and tidy!! We would definitely stay there again!!"
United States
Angela L.
$436 nightly
The price is $501
Nov 9 - Nov 10
Total with taxes and fees
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

18. 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
$332 nightly
The price is $382
Oct 14 - Oct 15
Total with taxes and fees
The Chester Hotel
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

19. Stunning Back Bay Studio Apartment

Stunning Back Bay Studio Apartment
Back Bay
8.8 out of 10, Excellent, (19 reviews)
"Cute place with a great location and responsive communication from the host. Would stay here again!"
United States
Lisa
$200 nightly
The price is $236
Nov 9 - Nov 10
Total with taxes and fees
Stunning Back Bay Studio Apartment
A wooden building entrance with two lanterns, a paved path, and a tree with pink leaves in the background.

20. Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#

Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#
Cambridgeport
9.4 out of 10, Exceptional, (44 reviews)
"Very friendly and easy walk to fenway"
United States
thomas p.
$297 nightly
The price is $340
Oct 22 - Oct 23
Total with taxes and fees
Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#
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

Hilton Boston Park Plaza

Hilton Boston Park Plaza

8/10 Good
"Very small room for paying over 2000 for 3 nights. Staff were great. No fridge in room. Great location."
Anette 3-night trip
Posted 2 hours ago
Hilton Boston Park Plaza

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 $157 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.