Winchester Vacation Rentals from $101: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Winchester?

Beautiful, Cozy Ultra Convenient Salem Home : This vacation home rental outside of Winchester is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

Check Winchester vacation rental availability

Vacation Rentals in Winchester

Winchester Vacation Rental Travel Info

Number of vacation rentals	71
Popular accommodation	Winchester private vacation homes
Known landmarks	New England Aquarium, Boston Museum of Fine Arts and Museum of Science
International airport	Boston, MA (BOS-Logan Intl.)

Other types of properties in Winchester you may be interested in

"Room was extremely small. Did not appreciate that there were 2 towers, one practical and lower end; the other with larger rooms more amenities and higher end. I did not realize there was a difference in types of rooms until I had reserved the room. However, it was a comfortable room very comfortable bed."

$281 total

includes taxes & fees

Jul 3 - Jul 4

"I enjoyed staying at the historic Omni Parker House, and the staff and service were excellent. I have zero complaints, and will look forward to my next visit!"

$247 total

includes taxes & fees

Jul 4 - Jul 5

Deluxe Room, 2 Double Beds (Bath in Room) | Premium bedding, down comforters, pillowtop beds, in-room safe

"Best property to stay at in Boston. Absolutely immaculate. You can walk anywhere from hotel. "

$167 total

includes taxes & fees

Jun 16 - Jun 17

Everything you need to know about Winchester vacation rentals

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

Winchester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $101 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation 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 vacation.

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 vacation rentals in Winchester?

Yes, we have vacation rentals in Winchester close to Winter Pond, or you can choose a more remote option if you're looking for a relaxing stay. Winchester is known for its soccer matches and lake views.

What are some of the best vacation home rentals in Winchester?

Beautiful, Cozy Ultra Convenient Salem Home: This vacation home rental outside of Winchester is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Winchester?

Family-friendly attractions include Winter Pond, whereas Middlesex Fells Reservation is a spot to enjoy the outdoors. TD Garden and Fenway Park are other popular places to visit in the area.

What are vacation rentals like in Winchester?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Winchester. Vacation rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.

Recent reviews of Winchester properties
Expedia verified reviews

5/5 Excellent

"I enjoyed staying at the historic Omni Parker House, and the staff and service were excellent. I have zero complaints, and will look forward to my next visit!"

A verified traveler stayed at Omni Parker House

Posted 6 hours ago