Search Vacation Homes in Winchester

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Winchester

Charming 2-bedroom building in delightful Hull with ocean view

10.0 out of 10, Exceptional, (2)
"Great place to stay we had a great time the host was awesome and easy to communicate with thank you for a wonderful weekend"
The price is SAR 751
SAR 1,317 total
includes taxes & fees
2 Sep - 3 Sep
Charming 2-bedroom building in delightful Hull with ocean view

Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

10.0 out of 10, Exceptional, (12)
"Easy to find, close to everything, very clean"
The price is SAR 672
SAR 1,548 total
includes taxes & fees
1 Sep - 2 Sep
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

2.0 star property
9.6 out of 10, Exceptional, (12)
"The property was lovely and well kept! And the location was amazing! Very nice and quiet neighborhood - definitely recommend "
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

NEW 2BR Historic Marblehead Home+Minutes to Beach

2.0 star property
10.0 out of 10, Exceptional, (10)
"My family stayed in October for a quick weekend getaway. Great location and easy to get to from Boston. Would definitely book again. "
The price is SAR 548
SAR 1,555 total
includes taxes & fees
2 Sep - 3 Sep
NEW 2BR Historic Marblehead Home+Minutes to Beach

Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!

10.0 out of 10, Exceptional, (20)
"Definitely will be staying there again!"
The price is SAR 1,167
SAR 1,840 total
includes taxes & fees
9 Sep - 10 Sep
Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!

Prime location in town w parking! Walk to beach, shops & harbor-Sleeps 8

10.0 out of 10, Exceptional, (15)
"Property as advertised. Great walkable location"
The price is SAR 1,689
SAR 3,114 total
includes taxes & fees
1 Sep - 2 Sep
Prime location in town w parking! Walk to beach, shops & harbor-Sleeps 8

Best location in Old Town home, 5 minutes to everything, enjoy the difference!

10.0 out of 10, Exceptional, (5)
The price is SAR 1,640
SAR 3,278 total
includes taxes & fees
20 Aug - 21 Aug
Best location in Old Town home, 5 minutes to everything, enjoy the difference!

Luxury 6 BR·7 Beds·4.5 BA house in charming Marblehead & walkable to the ocean

9.4 out of 10, Exceptional, (10)
The price is SAR 2,252
SAR 3,114 total
includes taxes & fees
24 Aug - 25 Aug
Luxury 6 BR·7 Beds·4.5 BA house in charming Marblehead & walkable to the ocean

The widow’s walk your very own spa experience

10.0 out of 10, Exceptional, (16)
"Great location with incredible views! House is great, lots of amenities - family loved it and already wants to go back!"
The widow’s walk your very own spa experience

Entire Lower Level of the House, Across From The Beach

9.8 out of 10, Exceptional, (17)
"Loved getting to visit the beach and the short drive to Salem!"
Entire Lower Level of the House, Across From The Beach

Entire 4BR 2 Bath Home l Minutes to Downtown Salem

2.0 star property
10.0 out of 10, Exceptional, (6)
"Great property. Can walk to many things and was a great hub to see beautiful Maine Owner was helpful and quick to respond. "
The price is SAR 942
SAR 2,163 total
includes taxes & fees
8 Sep - 9 Sep
Entire 4BR 2 Bath Home l Minutes to Downtown Salem

Downtown Salem Retreat 2BD

10.0 out of 10, Exceptional, (9)
"Enjoyed our time with this 2 bedroom in a city I love to visit. Nice walk to the center of town and beautiful area with a short walk to the water!Thank you!"
The price is SAR 465
SAR 967 total
includes taxes & fees
26 Aug - 27 Aug
Downtown Salem Retreat 2BD

Dwtn Beverly! 5 Min to Salem!

8.0 out of 10, Very Good, (2)
"Great location! Big Space! Love it!"
The price is SAR 338
SAR 860 total
includes taxes & fees
20 Aug - 21 Aug
Dwtn Beverly! 5 Min to Salem!

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

9.6 out of 10, Exceptional, (127)
"We stayed here for four days. It’s very clean nice beautiful place."
The price is SAR 747
SAR 1,672 total
includes taxes & fees
15 Sep - 16 Sep
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Historic 1686 Home Near Downtown l 5BR Retreat

2.0 star property
9.8 out of 10, Exceptional, (10)
"The house was perfect "
The price is SAR 1,099
SAR 2,724 total
includes taxes & fees
20 Aug - 21 Aug
Historic 1686 Home Near Downtown l 5BR Retreat

NEW 3BR Salem Townhouse Minutes to downtown

10.0 out of 10, Exceptional, (2)
"Perfect size, layout and accommodations for our family! Us and our adult kids! Equipped for lazy nights in with full kitchen and all the amenities of home, comfortable furnishings and clean!! Great porch for relaxing in the mornings and evenings! Perfect location, close enough to walk to all that salem has to offer yet far enough away from the business of it all!"
NEW 3BR Salem Townhouse Minutes to downtown

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

9.6 out of 10, Exceptional, (85)
"This place is so well located. So close everything. EXCELLENT.If one complaint sometimes upstairs people are very loud. Overall great stay"
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

*Spooky Halloween 2BR|Downtown+Parking|Witch House

9.4 out of 10, Exceptional, (41)
"Very clean, comfortable, with cute decor. 3 minute walk from an excellent bakery and coffee shop that serves breakfast sandwiches, we walked there every morning. Also close to the beach. Neighborhood was quiet. "
The price is SAR 751
SAR 1,459 total
includes taxes & fees
28 Aug - 29 Aug
*Spooky Halloween 2BR|Downtown+Parking|Witch House

284 - 5BR Boston-Peaceful House near England Aqua

9.8 out of 10, Exceptional, (67)
"Nice quiet street perfect for families and close to Boston."
The price is SAR 1,111
SAR 2,444 total
includes taxes & fees
21 Aug - 22 Aug
284 - 5BR Boston-Peaceful House near England Aqua

Central Beverly! 5 min to Salem!

Central Beverly! 5 min to Salem!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews