Vacation rentals in Stephenson

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Top-rated vacation rentals in Stephenson

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Guest suite in Summit Point

4.97 out of 5 average rating, 126 reviews

The Big Room - Historic Schoolhouse

Located one mile from the racetrack in the little village of Summit Point. This is a large renovated former classroom with 13' ceilings in the old Elementary School. Summit Point is a quiet place where you can take a leisurely stroll. There are even a couple sidewalks ;) We have 3 churches and a post office. The "Railside Market" serves food and sundries one block away. (currently has limited hours) Multiple food options are available in nearby Charles Town and lots more in Winchester Virginia!

Feb. 11 – 18

$204 CAD per night
Guest favourite

Apartment in Winchester

4.89 out of 5 average rating, 101 reviews

Modern Twist in Old Town! Rock n' Roll FUN!

Basil is your personal, 2 bedroom, Uber-stylish apartment, located in downtown Winchester with private parking! New & sparkling clean, enjoy high end finishes & creative design! Enjoy hot showers in the marble bath, sink into the shearling-covered couch relaxing in front of the new 55' smart TV, catch up with work in your private office, then walk to a great happy hour & dinner downtown! End your day cozying up in one of the two queen size, memory foam canopy beds! Basil is your perfect Airbnb!

Jul. 22 – 29

$218 CAD per night
Guest favourite

Home in Winchester

4.97 out of 5 average rating, 163 reviews

Cameron Charmer pristine w/double master suites

Take a step into pure luxury in this newly renovated 1930's charmer in up and coming downtown area of Winchester. Owners have spared no expense to make this the kind of place where guests can come & forget about the rest of the world ! Incredible top of the line centralized dine in kitchen, wide open & inviting living areas, two master suites each with walk in closets & baths up lovely custom pine staircase. Come spoil yourself a bit at the Cameron Charmer, you are sure to enjoy your stay !

Jan. 1 – 8

$245 CAD per night

Popular amenities for Stephenson vacation rentals

Other great vacation rentals in Stephenson

Guest favourite

Cabin in Lost River

4.96 out of 5 average rating, 108 reviews

Rustic and stylish mountain getaway

Jan. 8 – 15

$157 CAD per night
Superhost

Cottage in Gerrardstown

4.85 out of 5 average rating, 279 reviews

Wooded Mountain Retreat near Creek

May 26 – Jun. 2

$154 CAD per night
Guest favourite

Cabin in Shepherdstown

4.95 out of 5 average rating, 419 reviews

The Log Cabin

Oct. 17 – 24

$170 CAD per night
Guest favourite

Bungalow in Great Cacapon

4.9 out of 5 average rating, 460 reviews

Rooster Wrest in the Trees

Feb. 28 – Mar. 7

$168 CAD per night
Guest favourite

Cabin in Paw Paw

4.96 out of 5 average rating, 171 reviews

Easygoing

Jun. 6 – 13

$150 CAD per night
Guest favourite

Home in Winchester

4.93 out of 5 average rating, 148 reviews

Indigo Blue modern open vibe on tree lined street

Nov. 24 – Dec. 1

$287 CAD per night
Guest favourite

Tiny homes in Linville

4.99 out of 5 average rating, 593 reviews

The spring house at Thistle Hollow

Jul. 25 – Aug. 1

$185 CAD per night
Guest favourite

Cabin in Myersville

4.97 out of 5 average rating, 247 reviews

Cabin on Middle Creek - Myersville MD - Middletown

Mar. 19 – 26

$176 CAD per night
Guest favourite

Farm stay in Romney

4.98 out of 5 average rating, 281 reviews

Potomac Hills B&B on 15 Acre Farm with a View

Jul. 22 – 29

$205 CAD per night
Guest favourite

Guest suite in Bluemont

4.93 out of 5 average rating, 515 reviews

Blueridge Mountain Retreat Apartment

Nov. 18 – 25

$174 CAD per night
Guest favourite

Guest suite in Clear Brook

5.0 out of 5 average rating, 37 reviews

Bluebird Bungalow

Apr. 30 – May 7

$169 CAD per night
Guest favourite

Home in Winchester

4.91 out of 5 average rating, 23 reviews

Misty Meadow has quite setting in the country.

May 17 – 24

$134 CAD per night

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