Winchester Vacation Rentals

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Browse Select Winchester Vacation Homes

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

9.6 out of 10, Exceptional, (124)
"We stayed here for four days. It’s very clean nice beautiful place."
The price is CA $271
CA $606 total
includes taxes & fees
Aug 12 - Aug 13
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

9.8 out of 10, Exceptional, (166)
"So much better than staying at a hotel and separating our group of seven. Awesome stay, 10 out of 10 recommend"
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

Union Square House

9.6 out of 10, Exceptional, (75)
"Had a wonderful stay. Location great. House as described, clean, and comfortable. Would recommend for a stay. "
Union Square House

Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean

9.4 out of 10, Exceptional, (8)
The price is CA $816
CA $1,129 total
includes taxes & fees
Aug 12 - Aug 13
Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean

2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything

8.8 out of 10, Excellent, (36)
"Great stay, communication was amazing "
The price is CA $250
CA $568 total
includes taxes & fees
Jul 27 - Jul 28
2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything

Charming house with WiFi and AC in superb Randolph

9.6 out of 10, Exceptional, (9)
"This was a lovely little home in a quiet neighborhood that allowed us easy access to the highway for our daily adventures. The host was fabulous! We would definitely choose to stay there again if we ever return to the Boston area."
Charming house with WiFi and AC in superb Randolph

Boston's Best Vacation Home

9.8 out of 10, Exceptional, (54)
"Great location easy to get to all of Boston, clean and well maintained, large kitchen and living room. Enjoyed our stay"
Boston's Best Vacation Home

Spacious, New Renovation | Near T

10.0 out of 10, Exceptional, (7)
"The house was very nice, clean and comfortable. Had all the supplies we needed plus more included. Check-in and check-out were both super smooth. The host was very responsive. Overall great stay!"
Spacious, New Renovation | Near T

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

9.6 out of 10, Exceptional, (80)
"This property is perfect for 2 travelers or for a small family. Close to everything, very clean and easy to get to. Would 100% stay here again!"
The price is CA $203
CA $465 total
includes taxes & fees
Aug 3 - Aug 4
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

Leslie's Retreat: Spacious home ideally located to everything

10.0 out of 10, Exceptional, (236)
"We loved staying here! If we ever come back to Salem this is our first choice!"
Leslie's Retreat: Spacious home ideally located to everything

Entire Lower Level of the House, Across From The Beach

10.0 out of 10, Exceptional, (15)
"Loved getting to visit the beach and the short drive to Salem!"
The price is CA $306
CA $530 total
includes taxes & fees
Jul 31 - Aug 1
Entire Lower Level of the House, Across From The Beach

Hidden Gem right in the city of Boston!

9.8 out of 10, Exceptional, (21)
"We were in town for a conference for work and didn't want to stay in a hotel. The place was very clean and smelled amazing. Perfect space 3 friends to stay. Host was great she answered when reaching out before the stay and the arrival was seamless."
The price is CA $196
CA $561 total
includes taxes & fees
Aug 23 - Aug 24
Hidden Gem right in the city of Boston!

Clean, Contemporary Escape Near T

8.4 out of 10, Very good, (6)
"One parent and three teenagers in town for college tours. The location was “20” minutes via uber which was great. Everyone had room to decompress at the end of the day. Showers were great and beds were super comfortable. We will strongly consider staying there again for our next visit. "
Clean, Contemporary Escape Near T

Cozy Apartment | Near T

8.6 out of 10, Excellent, (13)
"This was much better than a hotel for my son and I. Comfy clean beds. Only downside was no real common area other than kitchen and only TV was in the kitchen. There’s no living room and no TVs in the bedrooms which were bigger than the kitchen sitting spot to use as an alternative. But great for a business person or someone only sleeping there. "
Cozy Apartment | Near T

Whole House Steps from Pleasant Pond

9.6 out of 10, Exceptional, (41)
"Beautiful area next to the pond, quiet and peaceful!"
Whole House Steps from Pleasant Pond

NEW 2BR Historic Marblehead Home+Minutes to Beach

2.0 star property
10.0 out of 10, Exceptional, (7)
"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 CA $241
CA $618 total
includes taxes & fees
Jul 31 - Aug 1
NEW 2BR Historic Marblehead Home+Minutes to Beach

The Bungalow @ Elm is located in the heart of Old Town Marblehead, MA.

9.8 out of 10, Exceptional, (34)
"Was a great spot for my spouse and I to visit again. We look forward to visiting this spot next year! "
The Bungalow @ Elm is located in the heart of Old Town Marblehead, MA.

Bright & Stylish 2BD/1BA in Town Center w Parking!

10.0 out of 10, Exceptional, (16)
"Definitely will be staying there again!"
The price is CA $418
CA $533 total
includes taxes & fees
Aug 5 - Aug 6
Bright & Stylish 2BD/1BA in Town Center w Parking!

Lake Access 4 Bed 3 Full Bath

10.0 out of 10, Exceptional, (17)
"What a great place to cook dinner and have a night with the girls! "
The price is CA $781
CA $1,546 total
includes taxes & fees
Jul 30 - Jul 31
Lake Access 4 Bed 3 Full Bath

NEW 3BR Salem Townhouse Minutes to downtown

10.0 out of 10, Exceptional, (1)
"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!"
The price is CA $356
CA $846 total
includes taxes & fees
Aug 6 - Aug 7
NEW 3BR Salem Townhouse Minutes to downtown
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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