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 Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winchester vacation rentals

Coffee/tea maker, fridge, microwave, oven

1. 2BR Historic Marblehead Home+Minutes to Beach

2BR Historic Marblehead Home+Minutes to Beach
Marblehead Historic District
10.0 out of 10, Exceptional, (25 reviews)
"Enjoyed our stay. "
United States
Mary D.
The price is SAR 1,151
SAR 2,322 total
includes taxes & fees
6 Sep - 7 Sep
2BR Historic Marblehead Home+Minutes to Beach
Marina

2. Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown

Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown
Marblehead
10.0 out of 10, Exceptional, (35 reviews)
"Adorable studio, has everything you could need! The host was super responsive and welcoming. Would absolutely stay there again. "
United States
Alisha J.
The price is SAR 713
SAR 1,300 total
includes taxes & fees
24 Aug - 25 Aug
Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown
Marina

3. ♥ 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
9.8 out of 10, Exceptional, (78 reviews)
"We had a wonderful stay! The studio was clean, cozy, and located in a beautiful historic house. It was also conveniently close to downtown, which made it easy to explore the area. The check-in instructions were clear and easy to follow. Communication with the host was excellent—they responded quickly and were very helpful whenever we had a question. Overall, we really enjoyed our stay and would definitely recommend this place!"
Canada
Camille
The price is SAR 338
SAR 944 total
includes taxes & fees
18 Aug - 19 Aug
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Interior

4. 1880 updated Victorian 1st floor, water views

1880 updated Victorian 1st floor, water views
Salem
10.0 out of 10, Exceptional, (29 reviews)
"We had a great stay! Place was beautiful and nearby to main attractions of Salem."
United States
Gregory
The price is SAR 821
SAR 1,051 total
includes taxes & fees
6 Sep - 7 Sep
1880 updated Victorian 1st floor, water views
Beach

5. Lovely two bedrooms in the great historic town

Lovely two bedrooms in the great historic town
Salem
9.6 out of 10, Exceptional, (88 reviews)
"Great place to stay and ver clean!"
United States
Sharon A.
The price is SAR 439
SAR 939 total
includes taxes & fees
24 Aug - 25 Aug
Lovely two bedrooms in the great historic town
Smart TV

6. 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, (17 reviews)
"Great location and ver comfortable stay."
United States
Michael C.
The price is SAR 583
SAR 1,360 total
includes taxes & fees
24 Aug - 25 Aug
Hocus Pocus Season is here! Don’t miss it!
Exterior

7. Coastal Charm: Lobster Châto

Coastal Charm: Lobster Châto
Swampscott
8.6 out of 10, Excellent, (9 reviews)
"Beautiful house & views,"
United States
Suzanne P.
The price is SAR 1,072
SAR 2,639 total
includes taxes & fees
24 Aug - 25 Aug
Coastal Charm: Lobster Châto
1 bedroom, desk, iron/ironing board, WiFi (free)

8. 1BR on Salem Common l Steps to Witch Museum l Fenced in Yard + Parking

1BR on Salem Common l Steps to Witch Museum l Fenced in Yard + Parking
Salem
10.0 out of 10, Exceptional, (39 reviews)
"This was a lovely place in the perfect location to explore Salem on foot. Very clean and comfortable with a fun vibe. "
United States
Laura B.
The price is SAR 852
SAR 1,706 total
includes taxes & fees
26 Aug - 27 Aug
1BR on Salem Common l Steps to Witch Museum l Fenced in Yard + Parking
1 bedroom, travel crib, WiFi (free), bed sheets

9. Re-listed: Adorable Condo Beverly - Salem - Halloween

Re-listed: Adorable Condo Beverly - Salem - Halloween
Beverly
10.0 out of 10, Exceptional, (23 reviews)
"Great location Lots of walking to good food and a few great vintage and thrift stores"
United States
Christine L.
The price is SAR 623
SAR 1,275 total
includes taxes & fees
8 Sep - 9 Sep
Re-listed: Adorable Condo Beverly - Salem - Halloween
TV

10. Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Downtown Salem
9.6 out of 10, Exceptional, (111 reviews)
"This place was perfect. Clean, a saved parking spot, within walking distance of everything you could want in Salem as well as the train station. Will definitely be looking into this if we decide to come back"
United States
Jacob
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Smart TV

11. Large 5BR Peaceful House near Perry Beach • Pet-Friendly w/Parking 284

Large 5BR Peaceful House near Perry Beach • Pet-Friendly w/Parking 284
Quincy
9.8 out of 10, Exceptional, (80 reviews)
"Nice quiet street perfect for families and close to Boston."
United States
Alisa O.
The price is SAR 919
SAR 2,276 total
includes taxes & fees
30 Aug - 31 Aug
Large 5BR Peaceful House near Perry Beach • Pet-Friendly w/Parking 284
Interior

12. Park & Play • Walk To Bars • Sleep in Luxury

Park & Play • Walk To Bars • Sleep in Luxury
Salem
10.0 out of 10, Exceptional, (81 reviews)
"The apartment is walkable to the major sites and good restaurants. The rooms and kitchen were clean. I enjoyed my stay."
United States
Jennifer G.
The price is SAR 965
SAR 1,942 total
includes taxes & fees
20 Aug - 21 Aug
Park & Play • Walk To Bars • Sleep in Luxury
TV

13. Central Salem Retreat 2bd W/ parking

Central Salem Retreat 2bd W/ parking
Salem
8.4 out of 10, Very Good, (21 reviews)
"It was very clean, a great location, and the host was super responsive and helpful!"
United States
Kristen N.
The price is SAR 702
SAR 1,246 total
includes taxes & fees
26 Aug - 27 Aug
Central Salem Retreat 2bd W/ parking
Interior

14. Salem Haunted Happenings Retreat

Salem Haunted Happenings Retreat
Salem
9.6 out of 10, Exceptional, (31 reviews)
"Great place!"
United States
Jeffrey
The price is SAR 529
SAR 1,040 total
includes taxes & fees
24 Aug - 25 Aug
Salem Haunted Happenings Retreat
TV, offices

15. Family-Friendly Salem Apt: Near Dtwn Sites!

Family-Friendly Salem Apt: Near Dtwn Sites!
Salem
10.0 out of 10, Exceptional, (40 reviews)
"House was impeccably clean and designed so beautifully. The location was a quiet little street full of lovely historic homes. The beds were so comfortable! Joe was a super nice and responsive host and helped us out when our flight got changed and our arrival time was several hours earlier than expected. We truly enjoyed our stay here."
United States
Sarah
The price is SAR 1,179
SAR 2,696 total
includes taxes & fees
24 Aug - 25 Aug
Family-Friendly Salem Apt: Near Dtwn Sites!
Exterior

16. Cozy Salem Getaway. Historic Home Near All the Sights

Cozy Salem Getaway. Historic Home Near All the Sights
Salem
9.6 out of 10, Exceptional, (59 reviews)
"Beautiful 2 bedroom, close to everything , host was wonderful, we will be back. "
United States
Charlene
The price is SAR 929
SAR 1,784 total
includes taxes & fees
26 Aug - 27 Aug
Cozy Salem Getaway. Historic Home Near All the Sights
3 bedrooms, desk, iron/ironing board, WiFi (free)

17. Cozy three-bedroom home close to Boston w/ plenty of parking

Cozy three-bedroom home close to Boston w/ plenty of parking
North Braintree
10.0 out of 10, Exceptional, (52 reviews)
"Great overall stay!"
United States
Chris R.
The price is SAR 912
SAR 1,908 total
includes taxes & fees
18 Aug - 19 Aug
Cozy three-bedroom home close to Boston w/ plenty of parking
Interior

18. Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.0 out of 10, Wonderful, (18 reviews)
"Easy, clean and a comfortable stay"
United States
Justin P.
The price is SAR 507
SAR 943 total
includes taxes & fees
18 Aug - 19 Aug
Enjoyable 2-bedroom lower level apartment in charming Lynn
Exterior detail

19. FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383

FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383
Quincy
9.8 out of 10, Exceptional, (52 reviews)
"Extraordinarily beautiful VRBO, very clean, convenient to highway, walking distance to several eateries, walk or quick drive to the Red Line to use to get into downtown Boston, and very responsive owner."
United States
Mark T.
The price is SAR 568
SAR 1,347 total
includes taxes & fees
16 Aug - 17 Aug
FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383
Interior

20. Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39

Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39
Quincy
9.6 out of 10, Exceptional, (54 reviews)
"Very clean and stay was enjoyable. "
United States
Sheldon S.
The price is SAR 839
SAR 1,697 total
includes taxes & fees
25 Aug - 26 Aug
Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39
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

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

10/10 Excellent
"Staff are super friendly property is close to everything"
Pinky Rose 3-night trip
Posted less than an hour ago
Club Quarters Hotel Faneuil Hall, Boston

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we have vacation rentals in Winchester close to Griffin Photography Museum, 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?

Lorenzo Inn: This vacation home rental outside of Winchester offers a garden, a barbecue grill, 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 vacation rentals are there in Winchester?

Choose from 3 Expedia vacation rentals in Winchester for a memorable vacation.

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 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.