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Check prices for these dates

Our top choices for Winchester holiday rentals

1. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,345 reviews)
"Great place. Friendly staff and comfortable rooms. We always stay at crescent when visiting Boston"
United States
Michael
The price is £126
includes taxes & fees
8 Nov - 9 Nov
Crescent Suites Hotel

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.
The price is £192
includes taxes & fees
15 Nov - 16 Nov
Charming 1-bedroom well located Garden Apartment in Historic West Medford

3. 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, (680 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 £195
includes taxes & fees
25 Nov - 26 Nov
Marriott Vacation Club® at Custom House, Boston

4. 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 £449
includes taxes & fees
15 Nov - 16 Nov
Enchanting Hidden Door Escape

5. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (338 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.
The price is £212
includes taxes & fees
8 Nov - 9 Nov
Near Boston Historic two-bedroom with Modern Amenities

6. 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 £412
includes taxes & fees
17 Nov - 18 Nov
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.

7. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (772 reviews)
"Great room: new and spacious. The kitchenette has everything i needed and more."
United States
Yelitza
The price is £177
includes taxes & fees
7 Dec - 8 Dec
Global Luxury Suites Downtown Boston

8. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (348 reviews)
"Great location, very comfortable apartment, great facilities, everyone was friendly and helpful!!!"
United States
antonio
The price is £220
includes taxes & fees
10 Nov - 11 Nov
Kasa Boston at Fenway

9. 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)
"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.
The price is £270
includes taxes & fees
8 Nov - 9 Nov
Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking

10. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (43 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
The price is £217
includes taxes & fees
22 Nov - 23 Nov
The Chester Hotel

11. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (473 reviews)
"Great location and the room was nicely decorated and clean!"
United States
Judy
The price is £160
includes taxes & fees
1 Dec - 2 Dec
Maverick Suites at 28 Fenway

12. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (355 reviews)
"The area was walkable and the room was great!"
United States
Edna
The price is £151
includes taxes & fees
1 Dec - 2 Dec
Maverick Suites at 89 Marion

13. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (215 reviews)
"Cozy, comfy and cute✨. Would def rent again❤️"
United States
Erica
The price is £192
includes taxes & fees
29 Nov - 30 Nov
Global Luxury Suites East Boston

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, (37 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 £283
includes taxes & fees
11 Nov - 12 Nov
Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking

15. 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
The price is £153
includes taxes & fees
6 Dec - 7 Dec
Maverick Suites at 245 Newbury St

16. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (246 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is £275
includes taxes & fees
23 Nov - 24 Nov
Charlesgate Suites

17. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (38 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
The price is £230
includes taxes & fees
8 Nov - 9 Nov
The Concord Hotel

18. 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 £291
includes taxes & fees
8 Nov - 9 Nov
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces

19. 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, (165 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
The price is £154
includes taxes & fees
9 Nov - 10 Nov
Maverick Suites at 40 Temple St

20. Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Chelsea
8.6 out of 10, Excellent, (10 reviews)
"It was close to Boston and the airport"
United States
Lewis
The price is £270
includes taxes & fees
9 Nov - 10 Nov
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
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.

Find holiday rentals that suit your style

Top Winchester Hotel Reviews

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, apart-hotels, 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 favorite 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 depends 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 £110 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 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.

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