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 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Winchester vacation rentals

A modern kitchen with wooden cabinets, a white refrigerator, and a coffee maker.

1. Garden Bliss Studio

Garden Bliss Studio
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.
$208 nightly
The price is $232
Nov 12 - Nov 13
Total with taxes and fees
Garden Bliss Studio
A residential house with a covered porch, a garage, and a well-maintained garden.

2. 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.
$226 nightly
The price is $252
Nov 12 - Nov 13
Total with taxes and fees
Charming 1-bedroom well located Garden Apartment in Historic West Medford
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, (774 reviews)
"Great room: new and spacious. The kitchenette has everything i needed and more."
United States
Yelitza
$203 nightly
The price is $233
Dec 9 - Dec 10
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, (1,354 reviews)
"Wehave stayed here several times and each time has been a pleasure."
United States
Kasandra
$140 nightly
The price is $157
Nov 13 - Nov 14
Total with taxes and fees
Crescent Suites Hotel
A spacious living room with a dining area, wooden columns, and a large window providing natural light.

5. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (339 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.
$251 nightly
The price is $280
Nov 12 - Nov 13
Total with taxes and fees
Near Boston Historic two-bedroom with Modern Amenities
A spacious living room with hardwood floors, a sofa, a chair, a coffee table, and a ceiling light fixture.

6. 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, (27 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.
$256 nightly
The price is $286
Nov 12 - Nov 13
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.

7. Enchanting Hidden Door Escape

Enchanting Hidden Door Escape
Stoneham
9.6 out of 10, Exceptional, (37 reviews)
"Property was very nice! Updated and clean!"
United States
Aimee M.
$568 nightly
The price is $610
Nov 24 - Nov 25
Total with taxes and fees
Enchanting Hidden Door Escape
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

8. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (477 reviews)
"Great location and the room was nicely decorated and clean!"
United States
Judy
$194 nightly
The price is $223
Nov 12 - Nov 13
Total with taxes and fees
Maverick Suites at 28 Fenway
A wooden hallway with a patterned floor leading to a door.

9. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (356 reviews)
"The area was walkable and the room was great!"
United States
Edna
$159 nightly
The price is $178
Nov 15 - Nov 16
Total with taxes and fees
Maverick Suites at 89 Marion
A staircase with white balusters and a wooden handrail, leading to a landing with a lamp and a small table.

10. 5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.

5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
Melrose
10.0 out of 10, Exceptional, (157 reviews)
"We enjoyed our stay! Great location, easy parking. Wonderful communication from host. Would stay again!"
United States
Martha W.
$495 nightly
The price is $552
Nov 16 - Nov 17
Total with taxes and fees
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
A row of brick buildings with storefronts, including a bakery and a liquor store.

11. 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, (219 reviews)
"Great location - plenty to do."
United States
Chloe
$168 nightly
The price is $193
Dec 6 - Dec 7
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.

12. 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, (168 reviews)
"great location near the commons. nice space for single traveler."
United States
Andrea
$151 nightly
The price is $173
Dec 1 - Dec 2
Total with taxes and fees
Maverick Suites at 40 Temple St
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

13. Stunning Back Bay Studio Apartment

Stunning Back Bay Studio Apartment
Back Bay
9.0 out of 10, Wonderful, (25 reviews)
"Great location."
United States
Chloe
$165 nightly
The price is $194
Dec 7 - Dec 8
Total with taxes and fees
Stunning Back Bay Studio Apartment
A brick building with a black front door, a staircase, and a well-maintained garden.

14. 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, (39 reviews)
"Great spot to stay when visiting Fenway."
United States
Jay G.
$189 nightly
The price is $205
Nov 15 - Nov 16
Total with taxes and fees
Free Parking at 1 Bed Basement Apt, Near BU & MIT
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

15. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (399 reviews)
"Good place to stay."
United States
Jaetaek
$139 nightly
The price is $160
Nov 23 - Nov 24
Total with taxes and fees
Premier Suites - Bay Village
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
$287 nightly
The price is $330
Nov 30 - Dec 1
Total with taxes and fees
Bright 2BR by Boston Waterfront
A bedroom with a bed, nightstands, a window, and a ceiling fan.

17. 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
Nov 13 - Nov 14
Total with taxes and fees
Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston
A spacious indoor swimming pool with large windows, modern seating, and a wooden ceiling.

18. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (216 reviews)
"Cozy, comfy and cute✨. Would def rent again❤️"
United States
Erica
$218 nightly
The price is $251
Nov 29 - Nov 30
Total with taxes and fees
Global Luxury Suites East Boston
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

19. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (557 reviews)
"We will definitely stay here again!"
United States
James
$155 nightly
The price is $178
Dec 2 - Dec 3
Total with taxes and fees
Temple Place Suites
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

20. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (45 reviews)
"I had a great stay at The Chester Hotel. Super cute vibe, easy check-in, and good location for where I needed to be for work. Bed is super comfy, the room aesthetic is great and the restaurant MIDA next door was really good!"
United States
Tracy
$270 nightly
The price is $310
Nov 12 - Nov 13
Total with taxes and fees
The Chester Hotel
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

Arcadian Hotel

Arcadian Hotel

10/10 Excellent
"Ver"
Sarah 1-night trip
Posted less than an hour ago
Arcadian Hotel

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.