Winchester Vacation Rentals

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Browse Select Winchester Vacation Homes

Casa Castor • Private Room 1

9.0 out of 10, Wonderful, (2)
"We loved staying at Judith's place! Much recommended!"
The price is CA $136
CA $183 total
includes taxes & fees
Sep 16 - Sep 17
Casa Castor • Private Room 1

NEW 2BR Historic Marblehead Home+Minutes to Beach

2.0 star property
10.0 out of 10, Exceptional, (13)
"We loved staying here, enjoying all that Marblehead had to offer. It was the perfect distance from both Salem and Boston and had lots to offer when we decided to stay in. We came on an unseasonably cold week but stayed nice and cozy in the Vrbo. Highly recommend! "
The price is CA $260
CA $646 total
includes taxes & fees
Sep 30 - Oct 1
NEW 2BR Historic Marblehead Home+Minutes to Beach

Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.

2.0 star property
9.8 out of 10, Exceptional, (9)
"Owner was super helpful helping with an early luggage drop off."
The price is CA $222
CA $548 total
includes taxes & fees
Sep 29 - Sep 30
Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.

Spacious & Convenient 1BR unit-20min to Boston

2.0 star property
9.8 out of 10, Exceptional, (10)
"The host stays in the same building and are friendly and helpful. We enjoy the timely response from th host, the clean and modern property, and the convenient location! "
The price is CA $232
CA $517 total
includes taxes & fees
Sep 15 - Sep 16
Spacious & Convenient 1BR unit-20min to Boston

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 CA $276
CA $606 total
includes taxes & fees
Oct 9 - Oct 10
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

Moody Salem Home Away From Home

10.0 out of 10, Exceptional, (14)
"We had such a wonderful time staying here! This location was a perfect drive to see all the sites and shops and a perfect place to relax after the day. The hosts were great to work with and we would highly recommend this place to anyone wanting to stay in Salem!"
The price is CA $323
CA $633 total
includes taxes & fees
Sep 24 - Sep 25
Moody Salem Home Away From Home

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

9.6 out of 10, Exceptional, (85)
"Perfect location. "
The price is CA $137
CA $388 total
includes taxes & fees
Sep 17 - Sep 18
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

CityScape: Urban Convenience Meets Affordability in this Modern City Living in the Heart of Chelsea!

2.0 star property
9.4 out of 10, Exceptional, (27)
"We stayed for a short trip for a concert, and it worked out great! The space was very comfortable and clean, and was very conveniently located! Would stay again!"
The price is CA $245
CA $703 total
includes taxes & fees
Sep 30 - Oct 1
CityScape: Urban Convenience Meets Affordability in this Modern City Living in the Heart of Chelsea!

Entire Lower Level of the House, Across From The Beach

9.8 out of 10, Exceptional, (17)
"We loved our stay at this gem by the ocean in Swampscott"
The price is CA $261
CA $475 total
includes taxes & fees
Sep 14 - Sep 15
Entire Lower Level of the House, Across From The Beach

Lovely 2 bedroom- kitchenette

2.0 star property
9.2 out of 10, Wonderful, (5)
"It served our purpose well. I would use it again"
The price is CA $199
CA $676 total
includes taxes & fees
Oct 8 - Oct 9
Lovely 2 bedroom- kitchenette

LUXE 3BR Near Boston, Airport, and Beach!

10.0 out of 10, Exceptional, (5)
"Loved the property! Would defiantly rent again! "
The price is CA $207
CA $530 total
includes taxes & fees
Sep 16 - Sep 17
LUXE 3BR Near Boston, Airport, and Beach!

PEACEFUL CHARM - Humble Luxury minutes from Boston, Beach & Casino

9.0 out of 10, Wonderful, (4)
"Barry was just the best. Great communication. Lovely home. Described just as listed maybe even nicer. We enjoyed our stay. Pretty close to everything. Thank you for sharing your home with us! "
The price is CA $260
CA $476 total
includes taxes & fees
Sep 15 - Sep 16
PEACEFUL CHARM - Humble Luxury minutes from Boston, Beach & Casino

Beacon Hill Studio with Full Kitchen, Short Walk to MGH, Multiple Train Lines

The price is CA $243
CA $553 total
includes taxes & fees
Sep 28 - Sep 29
Beacon Hill Studio with Full Kitchen, Short Walk to MGH, Multiple Train Lines

Charming 2-bedroom apartment with WiFi, AC in superb Canton

9.8 out of 10, Exceptional, (10)
"Very clean and nice rental! Would definitely stay again here. "
The price is CA $247
CA $314 total
includes taxes & fees
Sep 14 - Sep 15
Charming 2-bedroom apartment with WiFi, AC in superb Canton

Cozy House close to TUFTS, Harvard, MIT 3BR

10.0 out of 10, Exceptional, (13)
"Great stay and as advertised. Beds were very comfortable, unit was very clean, and ideal location for visiting Medford area!"
Cozy House close to TUFTS, Harvard, MIT 3BR

Charming 2-bedroom building in delightful Hull with ocean view

9.6 out of 10, Exceptional, (4)
"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 CA $276
CA $484 total
includes taxes & fees
Sep 14 - Sep 15
Charming 2-bedroom building in delightful Hull with ocean view

Seacity View

2.0 star property
The price is CA $668
CA $1,183 total
includes taxes & fees
Oct 8 - Oct 9
Seacity View

Dwtn Beverly! 5 Min to Salem!

9.0 out of 10, Wonderful, (4)
"Great location! Big Space! Love it!"
The price is CA $111
CA $300 total
includes taxes & fees
Sep 11 - Sep 12
Dwtn Beverly! 5 Min to Salem!

Easy access! 1br, 5 min walk to T train, easy access to Highway

9.0 out of 10, Wonderful, (12)
"Very clean like new! Lots of space very bright to work during the day with lots of windows. Plenty of parking and easy walk if you wanted the train or shopping. Host very responsive."
The price is CA $243
CA $516 total
includes taxes & fees
Sep 12 - Sep 13
Easy access! 1br, 5 min walk to T train, easy access to Highway

Cozy house close to Brandeis, Bentley, Moody St

9.4 out of 10, Exceptional, (6)
"We enjoy our stayed at the place.it’s nice and clean."
The price is CA $326
CA $820 total
includes taxes & fees
Sep 14 - Sep 15
Cozy house close to Brandeis, Bentley, Moody St
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

Winchester Vacation Homes information

Number of reviews
Accommodation
551 Vacation Homes
Lowest Price
CA $136
Highest Price
CA $900

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