Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Winchester vacation rentals

1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (344 reviews)
"Clean room, great location"
United States
Denis
$158 nightly
The price is $182
Mar 30 - Mar 31
Total with taxes and fees
Temple Place Suites
Premium Apartment | Living area | 24-inch Smart TV with digital channels

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (29 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
$299 nightly
The price is $344
Mar 30 - Mar 31
Total with taxes and fees
The Chester Hotel
Interior

Perfetto North End 1brm

Perfetto North End 1brm
North End
9.8 out of 10, Exceptional, (14 reviews)
"Great location- excellent place!"
United States
Deborah S.
$296 nightly
The price is $340
Mar 30 - Mar 31
Total with taxes and fees
Perfetto North End 1brm
Exterior detail

3BR pet-friendly Quincy house w/parking — near Adams Park

3BR pet-friendly Quincy house w/parking — near Adams Park
Quincy
9.8 out of 10, Exceptional, (47 reviews)
"very clean. comfortable beds. Very nice stay."
Germany
Stefanie K.
$348 nightly
The price is $389
Apr 5 - Apr 6
Total with taxes and fees
3BR pet-friendly Quincy house w/parking — near Adams Park
Smart TV

Hocus Pocus Season is here! Don’t miss it!

Hocus Pocus Season is here! Don’t miss it!
Salem
10.0 out of 10, Exceptional, (7 reviews)
"Great property!!!"
United States
Heather
$253 nightly
The price is $283
Mar 30 - Mar 31
Total with taxes and fees
Hocus Pocus Season is here! Don’t miss it!
Smart TV

Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking

Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking
Beverly
9.0 out of 10, Wonderful, (22 reviews)
"Cheerful decor, well-equipped kitchen, and clean. Good location in walking distance to restaurants. However, there was a musty smell throughout the building and rooms. "
United States
Julia
$248 nightly
The price is $277
Mar 30 - Mar 31
Total with taxes and fees
Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking
Living area

Exquisite North End 1brm

Exquisite North End 1brm
North End
9.6 out of 10, Exceptional, (32 reviews)
"Location was ideal "
Canada
Lindsay
$416 nightly
The price is $478
Apr 21 - Apr 22
Total with taxes and fees
Exquisite North End 1brm
Desk, laptop workspace, free WiFi, bed sheets

Bay Village Suites

Bay Village Suites
2.0 star property
Bay Village
6.6 out of 10, (259 reviews)
"This is a convenient property, close to the T and the Common. You will need to be able to walk up some narrow stairs, and adjust to sharing a common bathroom. I met the owner while he was shoveling snow after the nor'easter, and he could not have been nicer! Great value for the money, fairly quiet and I would stay again."
United States
Louise
$151 nightly
The price is $174
Mar 30 - Mar 31
Total with taxes and fees
Bay Village Suites
Property grounds

*2BR Downtown Witch House|Salem+Beverly|Hospitals

*2BR Downtown Witch House|Salem+Beverly|Hospitals
Beverly
10.0 out of 10, Exceptional, (33 reviews)
"The home was nicely renovated and comfortable and our hosts were quick to respond to questions. Check in and out was easy and we had a nice stay and will return. "
United States
Lawrence D.
$301 nightly
The price is $336
Mar 31 - Apr 1
Total with taxes and fees
*2BR Downtown Witch House|Salem+Beverly|Hospitals
Smart TV, books

Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (20 reviews)
"Perfect place for a Boston get away. Hosts are extremely polite, very transparent about parking. Very conveniently located to be anywhere in the city quickly. Will be staying here again in the future"
United States
Blāk R.
$212 nightly
The price is $244
Mar 31 - Apr 1
Total with taxes and fees
Bright 2BR by Boston Waterfront
1 bedroom, desk, iron/ironing board, WiFi

Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!
Downtown Boston
8.6 out of 10, Excellent, (18 reviews)
"Came to Boston to take a few college tours and this was a pretty central location. This property was also very close to several other places we were hoping to see while in town. Communication was great and check in was seamless. The property was clean and perfect for our stay. "
United States
elena d.
$196 nightly
The price is $230
Mar 30 - Mar 31
Total with taxes and fees
Perfect One Bedroom Stay In Downtown Boston!
TV

Prime Central 1brm in North End Boston

Prime Central 1brm in North End Boston
North End
9.6 out of 10, Exceptional, (25 reviews)
"Location was ideal and property was well-kept and organized. Definitely would recommend for future visits."
United States
Taye A.
$315 nightly
The price is $362
Apr 6 - Apr 7
Total with taxes and fees
Prime Central 1brm in North End Boston
Exterior

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.4 out of 10, Very Good, (8 reviews)
"Beautiful place right on historic Newbury Street. I’ll definitely return and I’d highly recommend this apartment."
United States
JEANPAUL
$275 nightly
The price is $296
Mar 30 - Mar 31
Total with taxes and fees
Stylish Back Bay Retreat, Steps from Prudential
1 bedroom, travel crib, free WiFi, bed sheets

Re-listed: Adorable Condo Beverly - Salem - Halloween

Re-listed: Adorable Condo Beverly - Salem - Halloween
Beverly
9.8 out of 10, Exceptional, (19 reviews)
"Small, clean ,quiet , great location Work definitely rent again"
United States
Nick S.
$222 nightly
The price is $247
Mar 30 - Mar 31
Total with taxes and fees
Re-listed: Adorable Condo Beverly - Salem - Halloween
Beach

*1710 Historic Downtown 2BR |Salem+Witch Trials

*1710 Historic Downtown 2BR |Salem+Witch Trials
Downtown Salem
10.0 out of 10, Exceptional, (65 reviews)
"Great location, walking distance to anywhere we wanted to go. Would not hesitate to stay again! "
United States
Pat M.
*1710 Historic Downtown 2BR |Salem+Witch Trials
Exterior

Free Parking at 1 Bed Basement Apt, Near BU & MIT

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.0 out of 10, Very Good, (10 reviews)
"Amazing location for the price. Check-in was super easy with clear instructions. Free parking was such a great perk for Boston. As for the house, despite a few visual damages (and 2 lightbulbs for the lamps not working), there was not much to complain about. Would recommend "
United States
Mai
$199 nightly
The price is $217
Apr 5 - Apr 6
Total with taxes and fees
Free Parking at 1 Bed Basement Apt, Near BU & MIT
TV

Central Salem Retreat 2bd W/ parking

Central Salem Retreat 2bd W/ parking
Salem
9.2 out of 10, Wonderful, (15 reviews)
"It was very clean, a great location, and the host was super responsive and helpful!"
United States
Kristen N.
$227 nightly
The price is $230
Mar 30 - Mar 31
Total with taxes and fees
Central Salem Retreat 2bd W/ parking
Marina

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Marblehead Historic District
10.0 out of 10, Exceptional, (72 reviews)
"Super convenient location; quaint old building; spacious apartment with comfortable bed, seating, and well appointed kitchen and bath. Easy checkin, checkout, and access. Thanks for a great stay!"
United States
Barbara D.
$213 nightly
The price is $238
Apr 1 - Apr 2
Total with taxes and fees
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Dining

North End Entire House

North End Entire House
North End
10.0 out of 10, Exceptional, (19 reviews)
"Great location in the Northend!"
United States
Carol T.
$449 nightly
The price is $517
Mar 30 - Mar 31
Total with taxes and fees
North End Entire House
Exterior

Coastal Charm: Lobster Châto

Coastal Charm: Lobster Châto
Swampscott
8.4 out of 10, Very Good, (6 reviews)
"Beautiful house & views,"
United States
Suzanne P.
$523 nightly
The price is $557
Mar 30 - Mar 31
Total with taxes and fees
Coastal Charm: Lobster Châto
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

The Dagny Boston

The Dagny Boston

10/10 Excellent
"Great hotel. Nicely located in the city. "
Magdiel 3-night trip
Posted 1 hour ago
The Dagny Boston

Find out more about Winchester

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 $147 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.

Explore a world of travel with Expedia

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?

Spacious, New Renovation | Near T: 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 6 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?

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 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.