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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (14 reviews)
"Will not be disappointed!"
United States
Dave O.
The price is CA $221
CA $415 total
includes taxes & fees
Sep 30 - Oct 1
Charming 1-bedroom well located Garden Apartment in Historic West Medford
A stone house with a garden bed, a hose, and a brick pathway.

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, (66 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.
The price is CA $204
CA $414 total
includes taxes & fees
Oct 5 - Oct 6
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

3. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,290 reviews)
"The full kitchen is amazing. The laundry soap provided was a nice surprise! It’s clean, quiet and gives a home like feeling for a hotel."
United States
Mrs. Andrea
The price is CA $210
CA $234 total
includes taxes & fees
Oct 18 - Oct 19
Crescent Suites Hotel
A staircase with white balusters and a wooden handrail, leading to a landing with a lamp and a small table.

4. 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, (153 reviews)
"We enjoyed our stay! The house is beautiful, clean and as described. Greg was extremely helpful and very quick to respond. Neighborhood felt safe and would definitely stay again!"
United States
KATIE G.
The price is CA $350
CA $791 total
includes taxes & fees
Sep 29 - Sep 30
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
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, (329 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
The price is CA $283
CA $410 total
includes taxes & fees
Sep 30 - Oct 1
Near Boston Historic two-bedroom with Modern Amenities
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, (319 reviews)
"Room was clean, neat area."
United States
Keir
The price is CA $173
CA $319 total
includes taxes & fees
Sep 29 - Sep 30
Maverick Suites at 89 Marion
A living room with a sofa, a glass coffee table, a TV mounted on the wall, a wooden floor, and a window with a view of trees.

7. NEW Modern Apartment Near Boston & Harvard Square.

NEW Modern Apartment Near Boston & Harvard Square.
Watertown
10.0 out of 10, Exceptional, (53 reviews)
"That was the most comfortable bed I have slept in away from home!"
United States
Kimberly M.
The price is CA $175
CA $313 total
includes taxes & fees
Oct 25 - Oct 26
NEW Modern Apartment Near Boston & Harvard Square.
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.

8. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (44 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
The price is CA $211
CA $524 total
includes taxes & fees
Oct 4 - Oct 5
Bright 2BR by Boston Waterfront
A hallway with a welcome sign, a kitchen area with a counter and stools, and a patterned rug.

9. Bee-Themed Stay Near Boston – A Sweet and Unique Getaway

Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
Billerica
10.0 out of 10, Exceptional, (17 reviews)
"It was a great stay. The place was cosy and had everything you need and stuff you forgot to bring . I will definitely be staying here again."
United States
Jonathan
The price is CA $258
CA $448 total
includes taxes & fees
Oct 11 - Oct 12
Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
A modern kitchen with dark cabinets, a white countertop, stainless steel appliances, and a central island with bar stools.

10. 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, (30 reviews)
"Beautiful unit with attentive host and safe parking. We enjoyed our stay."
United States
Debbie L.
The price is CA $229
CA $654 total
includes taxes & fees
Oct 4 - Oct 5
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
A wooden building entrance with two lanterns, a paved path, and a tree with pink leaves in the background.

11. 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.
The price is CA $267
CA $516 total
includes taxes & fees
Oct 14 - Oct 15
Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#
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, (350 reviews)
"Location is great"
United States
Eria
The price is CA $171
CA $269 total
includes taxes & fees
Sep 30 - Oct 1
Premier Suites - Bay Village
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, (24 reviews)
"Great room! Cool place to stay. We walked everywhere and stuff was close by. Woud stay here again"
United States
Cotie
The price is CA $284
CA $506 total
includes taxes & fees
Sep 30 - Oct 1
The Concord Hotel
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

14. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (38 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is CA $269
CA $488 total
includes taxes & fees
Sep 30 - Oct 1
The Chester Hotel
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

15. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (483 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is CA $188
CA $306 total
includes taxes & fees
Oct 5 - Oct 6
Temple Place Suites
A white table with a vase of white orchids, a white chair, and a view of a cityscape through a window with a black frame.

16. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.6 out of 10, Good, (175 reviews)
"Well located"
United States
Evelyn
The price is CA $206
CA $367 total
includes taxes & fees
Sep 30 - Oct 1
Maverick Suites at 400 Columbus Ave
A hallway with brick walls and a polished floor, leading to a door.

17. 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, (26 reviews)
"Easy, clean and a comfortable stay"
United States
Justin P.
The price is CA $191
CA $352 total
includes taxes & fees
Oct 21 - Oct 22
Enjoyable 2-bedroom lower level apartment in charming Lynn
A brick building with a black front door, a staircase, and a well-maintained garden.

18. 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
The price is CA $167
CA $349 total
includes taxes & fees
Oct 7 - Oct 8
Free Parking at 1 Bed Basement Apt, Near BU & MIT
A row of brick buildings with storefronts, including a bakery and a liquor store.

19. 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, (203 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is CA $282
CA $454 total
includes taxes & fees
Oct 29 - Oct 30
Maverick Suites at 245 Newbury St
A building with a sign reading "GREEN TURTLE" and a dock with red chairs.

20. Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.

Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.
Charlestown
10.0 out of 10, Exceptional, (258 reviews)
"Loved this experience!!! Would book this again! So convenient to see Boston! "
United States
Ellen Z.
The price is CA $384
CA $691 total
includes taxes & fees
Oct 7 - Oct 8
Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.
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

The Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"Great location, right by the Commons and near all the spots to walk and see Boston. Liked the bar on the main, although bit small.... no real restaurant on site, but lots in the area."
Gaby 2-night trip
Posted 1 hour ago
The Godfrey Hotel Boston

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester vacation rentals we have selected for you start as low as CA $234 per night. Entering your travel dates in the search wizard 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.