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 Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Winchester holiday rentals

A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

1. 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, (664 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is AU$650
includes taxes & fees
11 Sept - 12 Sept
Marriott Vacation Club® at Custom House, Boston
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

2. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (740 reviews)
"Great for the price; central to everything"
United States
afshin
The price is AU$504
includes taxes & fees
10 Sept - 11 Sept
Global Luxury Suites Downtown Boston
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

3. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (314 reviews)
"Everything is good"
United States
Kilyen
The price is AU$394
includes taxes & fees
20 Sept - 21 Sept
Kasa Boston at Fenway
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

4. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (21 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 AU$488
includes taxes & fees
10 Sept - 11 Sept
The Concord Hotel
A modern hotel room with a bed, a desk, a sofa, and a dining area.

5. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (232 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is AU$536
includes taxes & fees
10 Sept - 11 Sept
Charlesgate Suites
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

6. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (418 reviews)
"Great property beautiful vintage building great location"
United States
James
The price is AU$452
includes taxes & fees
14 Sept - 15 Sept
Maverick Suites at 28 Fenway
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.

7. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.6 out of 10, Good, (171 reviews)
"Well located"
United States
Evelyn
The price is AU$385
includes taxes & fees
14 Sept - 15 Sept
Maverick Suites at 400 Columbus Ave
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

8. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (337 reviews)
"Location is great"
United States
Eria
The price is AU$237
includes taxes & fees
9 Sept - 10 Sept
Premier Suites - Bay Village
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

9. 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 AU$431
includes taxes & fees
10 Sept - 11 Sept
The Chester Hotel
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

10. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (463 reviews)
"The Property was comfortable, close to public transport, The Goston Common and lots of lively eateries."
United Kingdom
Lisa
The price is AU$280
includes taxes & fees
10 Sept - 11 Sept
Temple Place Suites
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

11. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (145 reviews)
"Worth the stay"
Canada
Akansha
The price is AU$344
includes taxes & fees
10 Sept - 11 Sept
Maverick Suites at 40 Temple St
A row of brick buildings with storefronts, including a bakery and a liquor store.

12. 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, (202 reviews)
"Great location, really cool place!"
United States
lane
The price is AU$377
includes taxes & fees
9 Sept - 10 Sept
Maverick Suites at 245 Newbury St
A modern kitchen with a central island, a dining area with a round table and chairs, and a large window providing a view of the city at night.

13. The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (40 reviews)
"This place is absolutely stunning I would definitely book again. "
United States
Klaudia
The price is AU$1,149
includes taxes & fees
14 Sept - 15 Sept
The Monty Boston
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

14. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,265 reviews)
"Friendly staff. Bed was very comfortable and the kitchen was a plus!"
United States
Evelyn
The price is AU$250
includes taxes & fees
9 Sept - 10 Sept
Crescent Suites Hotel
A wooden hallway with a patterned floor leading to a door.

15. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (310 reviews)
"Stayed in the economy suite, very suitable for a couple! Very clean room and I have never had an easier check-in process!!"
United States
Paula
The price is AU$316
includes taxes & fees
9 Sept - 10 Sept
Maverick Suites at 89 Marion

16. Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (21 reviews)
"Great location, close to the T line, grocery store nearby. Clean, quiet and very comfortable accommodations, especially the best bed I’ve slept in at a rental location. Had everything we needed, looking forward to coming back!"
United States
Lori
The price is AU$562
includes taxes & fees
14 Sept - 15 Sept
Symple Live
A living room with a black leather sofa, a glass coffee table, a brick fireplace, and a TV mounted on the wall.

17. Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
8.0 out of 10, Very good, (85 reviews)
"It was very close to stores to go shopping and amazing spot to get last minute reservations for dinner"
United States
Talyciah
The price is AU$354
includes taxes & fees
9 Sept - 10 Sept
Maverick Suites at 402 Columbus Ave
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, (207 reviews)
"Good place and nice location but bed sheets and pillows were stained and had hair on them which is unacceptable."
United Kingdom
Leigh
The price is AU$536
includes taxes & fees
13 Sept - 14 Sept
Global Luxury Suites East Boston

19. Apt in Historic Lynn Neighborhood: 5 Mi to Salem!

Apt in Historic Lynn Neighborhood: 5 Mi to Salem!
3.0 star property
Lynn
The price is AU$564
includes taxes & fees
12 Sept - 13 Sept
Apt in Historic Lynn Neighborhood: 5 Mi to Salem!
A traditional black wooden house with multiple gabled roofs, surrounded by a well-maintained garden with various flowering plants and a brick pathway.

20. Seacity View

Seacity View
2.0 star property
Swampscott
7.0 out of 10, Good, (2 reviews)
"Beautiful house!"
United States
carla n
The price is AU$881
includes taxes & fees
14 Sept - 15 Sept
Seacity View
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 Dagny Boston

The Dagny Boston

10/10 Excellent
"Great stay"
Jason 1-night trip
Posted less than an hour ago
The Dagny Boston

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winchester holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as AU$237 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday 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 holiday.

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 holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Griffin Photography Museum, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its football matches and lake views.

What are some of the best holiday rentals that Winchester has to offer?

Cozy Salem Getaway. Historic Home Near All the Sights: This holiday home rental outside of Winchester offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Winchester?

Choose from 3 Expedia holiday rentals in Winchester for a memorable holiday.

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 holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips.