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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Our top choices for Winchester holiday rentals

1. 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, (64 reviews)
"Excellent communication with hosts, perfect location for so many sites in the region, lovely space just as advertised. "
United States
Lynn C.
The price is NZ$440
includes taxes & fees
12 Aug - 13 Aug
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.

2. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (36 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is NZ$510
includes taxes & fees
12 Aug - 13 Aug
The Chester Hotel

3. 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, (31 reviews)
"Friendly hosts"
United States
Jan
The price is NZ$363
includes taxes & fees
13 Aug - 14 Aug
Free Parking at 1 Bed Basement Apt, Near BU & MIT

4. Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
9.6 out of 10, Exceptional, (9 reviews)
"Perfect location! On a quiet street right in the heart of the Back Bay. Can easily walk to restaurants, grocery stores, the Prudential Center, and pubic transportation. Close to the nearby colleges which was helpful for our stay. We were able to support our college-age kid through a tough moment. It was clean, comfortable, and management was responsive and friendly. It was easy in and out. We’ll definitely come back. This would be perfect if you had any kind of medical emergency or needed to...
United States
Gretchen J.
The price is NZ$532
includes taxes & fees
19 Aug - 20 Aug
Light-filled Studio | Back Bay

5. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.8 out of 10, Good, (141 reviews)
"Worth the stay"
Canada
Akansha
The price is NZ$431
includes taxes & fees
12 Aug - 13 Aug
Maverick Suites at 40 Temple St

6. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (434 reviews)
"Great location so close to everything"
United States
Hunter
The price is NZ$299
includes taxes & fees
12 Aug - 13 Aug
Temple Place Suites

7. 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, (197 reviews)
"Great location, really cool place!"
United States
lane
The price is NZ$448
includes taxes & fees
18 Aug - 19 Aug
Maverick Suites at 245 Newbury St

8. Cozy Studio Steps from Boston Common and Theaters

Cozy Studio Steps from Boston Common and Theaters
Bay Village
7.6 out of 10, Good, (15 reviews)
"All good, would definitely stay again"
United States
Dan C.
The price is NZ$464
includes taxes & fees
16 Aug - 17 Aug
Cozy Studio Steps from Boston Common and Theaters

9. Great Apartment on River/ Harvard Square two blocks

Great Apartment on River/ Harvard Square two blocks
West Cambridge
8.6 out of 10, Excellent, (38 reviews)
"Perfect location to explore Cambridge."
United States
Anonymous traveller
The price is NZ$530
includes taxes & fees
18 Aug - 19 Aug
Great Apartment on River/ Harvard Square two blocks

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, (28 reviews)
"Beautiful unit with attentive host and safe parking. We enjoyed our stay."
United States
Debbie L.
The price is NZ$685
includes taxes & fees
16 Aug - 17 Aug
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces

11. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.6 out of 10, Exceptional, (40 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 NZ$499
includes taxes & fees
12 Aug - 13 Aug
Bright 2BR by Boston Waterfront

12. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.0 out of 10, Good, (12 reviews)
"Clean room and linens, great location and comfortable bed. Only complaint is the street noise and sounds from residents in upstairs apartment which was kind of loud. All things considered I’d stay again as it was a good value spot"
United States
Nancy
The price is NZ$488
includes taxes & fees
12 Aug - 13 Aug
The Concord Hotel

13. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,245 reviews)
"The hotel was conveniently located with lots of good dining options nearby. The room was very clean, quiet and comfortable ."
United States
CHRISTINE
The price is NZ$293
includes taxes & fees
5 Sept - 6 Sept
Crescent Suites Hotel

14. Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
Downtown Boston
9.0 out of 10, Wonderful, (2 reviews)
"Host was very communicative. The apartment was very clean and spacious and the location was fantastic! A lot of things in walking distance and train stop nearby for getting to other parts of the city was convenient. I would highly recommend this host and their space! Thank you for your hospitality! Would love to come back."
United States
Rachael M.
The price is NZ$594
includes taxes & fees
20 Aug - 21 Aug
Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

15. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (402 reviews)
"Easy to move-in, location is good for traveler. The shower room not that clean, some hair from previous guests, just clean it can be manage by guest."
Taiwan
LICHIEH
The price is NZ$461
includes taxes & fees
12 Aug - 13 Aug
Maverick Suites at 28 Fenway

16. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (324 reviews)
"Good location, good place to stay if you plan to just sleep and not spend so much time in a home!!"
United States
Osha
The price is NZ$280
includes taxes & fees
12 Aug - 13 Aug
Premier Suites - Bay Village

17. Primo North End Studio

Primo North End Studio
North End
9.4 out of 10, Exceptional, (19 reviews)
"Great place, amazing location!"
United States
Christopher W.
The price is NZ$574
includes taxes & fees
16 Aug - 17 Aug
Primo North End Studio

18. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (224 reviews)
"Very nice room and close to fenway"
United States
timothy
The price is NZ$641
includes taxes & fees
16 Aug - 17 Aug
Charlesgate Suites

19. Downtown Studio | Students Welcome | W/D in unit

Downtown Studio | Students Welcome | W/D in unit
Downtown Boston
9.4 out of 10, Exceptional, (3 reviews)
"Was worth the price all around"
United States
steven l.
The price is NZ$540
includes taxes & fees
18 Aug - 19 Aug
Downtown Studio | Students Welcome | W/D in unit

20. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (161 reviews)
"Well located"
United States
Evelyn
The price is NZ$405
includes taxes & fees
26 Aug - 27 Aug
Maverick Suites at 400 Columbus Ave
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

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 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 NZ$280 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 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?

Lorenzo Inn: This holiday home rental outside of Winchester offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.