Winchester Holiday Rentals

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Holiday Rentals in Winchester

Our top choices for Winchester holiday rentals

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93

7.4 out of 10, Good, (30)
"The property was in a nice, quiet area and it was especially easy to get to and from the highway leading to Downtown Boston. 5 min drive to the Orange Line - Oak Grove station"
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93

Temple Place Suites

2.5 star property
7.0 out of 10, Good, (263)
"Very convenient place to stay, near transportation and waking distance to historic points and shopping. "
The price is AU$307
includes taxes & fees
7 Sept - 8 Sept
Temple Place Suites

Premier Suites - Bay Village

2.0 star property
6.2 out of 10, (208)
"Great stay and close to my monthly event site so I hope to come back again."
The price is AU$485
includes taxes & fees
12 Sept - 13 Sept
Premier Suites - Bay Village

Bay Village Suites

2.0 star property
6.4 out of 10, (203)
"The location is awesome!"
The price is AU$265
includes taxes & fees
6 Sept - 7 Sept
Bay Village Suites

Global Luxury Suites Downtown Boston

4.0 star property
8.0 out of 10, Very good, (594)
"Good location"
Global Luxury Suites Downtown Boston

Maverick Suites at 28 Fenway

3.0 star property
8.8 out of 10, Excellent, (263)
"Great location"
The price is AU$331
includes taxes & fees
23 Sept - 24 Sept
Maverick Suites at 28 Fenway

Crescent Suites Hotel

3.0 star property
9.6 out of 10, Exceptional, (1074)
"Very pleased with hotel. "
Crescent Suites Hotel

907 Main Hotel Central Square, Sonder by Marriott Bonvoy

4.0 star property
8.2 out of 10, Very good, (518)
"Great hotel!"
The price is AU$428
includes taxes & fees
21 Sept - 22 Sept
907 Main Hotel Central Square, Sonder by Marriott Bonvoy

Maverick Suites at 89 Marion

2.0 star property
8.4 out of 10, Very good, (251)
"I liked the location very much! "
The price is AU$342
includes taxes & fees
30 Sept - 1 Oct
Maverick Suites at 89 Marion

The Chester Hotel

4.0 star property
9.0 out of 10, Wonderful, (19)
"Great place to stay in Boston and near colleges."
The price is AU$669
includes taxes & fees
21 Sept - 22 Sept
The Chester Hotel

Maverick Suites at 40 Temple St

2.0 star property
7.4 out of 10, Good, (90)
"Loved how convenient it was to tranportation. As well as the tall ceilings felt very homey and luxurious at the samr time."
The price is AU$436
includes taxes & fees
30 Sept - 1 Oct
Maverick Suites at 40 Temple St

Maverick Suites at 245 Newbury St

2.0 star property
8.2 out of 10, Very good, (139)
"Clean. Great location. "
The price is AU$460
includes taxes & fees
30 Sept - 1 Oct
Maverick Suites at 245 Newbury St

Global Luxury Suites East Boston

4.0 star property
6.8 out of 10, (162)
"All was great, the appartement itself, the location and not the least the use of the gym, dundeck and pool. Really a great place to enjoy Boston!"
The price is AU$511
includes taxes & fees
28 Sept - 29 Sept
Global Luxury Suites East Boston

Charlesgate Suites

3.5 star property
9.4 out of 10, Exceptional, (186)
"Awesome property, conveniently located near everything, especially Fenway. Definitely will stay here again. "
The price is AU$713
includes taxes & fees
7 Sept - 8 Sept
Charlesgate Suites

No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy

4.0 star property
9.4 out of 10, Exceptional, (933)
"Beautiful property "
The price is AU$515
includes taxes & fees
21 Sept - 22 Sept
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy

Maverick Suites at 402 Columbus Ave

2.5 star property
7.8 out of 10, Good, (60)
"Easy to walk to and from T stations near by. Decently priced and was overall a great place to stay!"
The price is AU$424
includes taxes & fees
30 Sept - 1 Oct
Maverick Suites at 402 Columbus Ave

Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway

4.0 star property
8.8 out of 10, Excellent, (262)
"Great location for a family close to Fenway. Beds were a little hard. "
The price is AU$541
includes taxes & fees
21 Sept - 22 Sept
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway

The Monty Boston

2.5 star property
9.6 out of 10, Exceptional, (20)
"Everything was great to live in this place! Very spacious and convenient."
The price is AU$1,165
includes taxes & fees
8 Sept - 9 Sept
The Monty Boston

Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay

3.5 star property
8.8 out of 10, Excellent, (70)
"Great place , size of the apartment , very clean"
The price is AU$615
includes taxes & fees
28 Sept - 29 Sept
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay

Maverick Suites at 400 Columbus Ave

2.0 star property
7.4 out of 10, Good, (120)
"Great place to stay with close proximity to the city "
The price is AU$312
includes taxes & fees
30 Sept - 1 Oct
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

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$265 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?

Casa Castor • Private Room 1: This holiday home rental outside of Winchester has air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge to make your meal-planning easier.

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.