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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Winchester holiday 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
The price is AU$384
includes taxes & fees
17 Nov - 18 Nov
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, (4 reviews)
"Nice Appartement!Bus round the corner, very quiet!"
United States
Holger V.
The price is AU$399
includes taxes & fees
17 Nov - 18 Nov
Train to Boston! Cozy Apartment in Winchester
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, (1,329 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is AU$213
includes taxes & fees
4 Nov - 5 Nov
Crescent Suites Hotel
A residential house with a covered porch, a garage, and a well-maintained garden.

4. 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.
The price is AU$383
includes taxes & fees
2 Nov - 3 Nov
Charming 1-bedroom well located Garden Apartment in Historic West Medford
A modern living room with a sectional sofa, a wooden coffee table, and a fireplace.

5. 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.
The price is AU$924
includes taxes & fees
27 Oct - 28 Oct
Enchanting Hidden Door Escape
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

6. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (678 reviews)
"I can’t believe this property is a hotel and not a historic landmark. If you like historical places this is the place to stay in Boston."
United States
Benny
The price is AU$475
includes taxes & fees
23 Nov - 24 Nov
Marriott Vacation Club® at Custom House, Boston
A spacious living room with a dining area, wooden columns, and a large window providing natural light.

7. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (336 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
The price is AU$454
includes taxes & fees
26 Oct - 27 Oct
Near Boston Historic two-bedroom with Modern Amenities
A staircase with white balusters and a wooden handrail, leading to a landing with a lamp and a small table.

8. 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, (156 reviews)
"We enjoyed our stay! Great location, easy parking. Wonderful communication from host. Would stay again!"
United States
Martha W.
The price is AU$793
includes taxes & fees
28 Oct - 29 Oct
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
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, (41 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
The price is AU$369
includes taxes & fees
9 Nov - 10 Nov
The Chester Hotel
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

10. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (335 reviews)
"Clean hotel. The space was very nice and open, Very accessible to everything I needed"
United States
Krista
The price is AU$423
includes taxes & fees
9 Nov - 10 Nov
Kasa Boston at Fenway
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

11. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (767 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is AU$350
includes taxes & fees
22 Nov - 23 Nov
Global Luxury Suites Downtown Boston
A wooden hallway with a patterned floor leading to a door.

12. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (346 reviews)
"The area was walkable and the room was great!"
United States
Edna
The price is AU$273
includes taxes & fees
15 Nov - 16 Nov
Maverick Suites at 89 Marion
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

13. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (456 reviews)
"Really pretty well maintained accomodation close to a lot of cool things to do in boston. its also pretty close to the train and bus station which was helpful to get around"
United States
Rakshitha
The price is AU$326
includes taxes & fees
11 Nov - 12 Nov
Maverick Suites at 28 Fenway
A living room with a sofa, a glass coffee table, and a staircase.

14. Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking

Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking
Everett
10.0 out of 10, Exceptional, (36 reviews)
"House was clean and comfortable, area had a convenient store nearby and local restaurants to eat. We had a great stay."
United States
Elizabeth
The price is AU$589
includes taxes & fees
27 Oct - 28 Oct
Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking
A modern kitchen with dark cabinets, a white countertop, stainless steel appliances, and a central island with bar stools.

15. 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.
The price is AU$604
includes taxes & fees
8 Nov - 9 Nov
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
A modern hotel room with a bed, a desk, a sofa, and a dining area.

16. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (243 reviews)
"Spacers, convenient location"
United States
Svetlana
The price is AU$527
includes taxes & fees
22 Nov - 23 Nov
Charlesgate Suites
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, (36 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
The price is AU$445
includes taxes & fees
22 Nov - 23 Nov
The Concord Hotel
A row of brick buildings with storefronts, including a bakery and a liquor store.

18. 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, (209 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is AU$343
includes taxes & fees
15 Nov - 16 Nov
Maverick Suites at 245 Newbury St
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, (527 reviews)
"Great location, good value and comfortable beds"
United States
Deborah
The price is AU$237
includes taxes & fees
23 Nov - 24 Nov
Temple Place Suites
A deck with wicker furniture and a table, overlooking a marina with boats.

20. Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown

Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown
Thompson Square - Bunker Hill
9.8 out of 10, Exceptional, (90 reviews)
"The host was super helpful and our family enjoyed the unique location."
United States
Katie P.
Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown
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

8/10 Good
"Great location. Bad mattress"
Nicola J 1-night trip
Posted 5 hours ago
Wyndham Boston Beacon Hill

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$212 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 Winter Pond, 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?

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots: This holiday 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with 1 hot tub and a selection of books.

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. Fenway Park and Encore Boston Harbor 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.