Massies Mill Rentals

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74 Houses

(3) Excellent 

30

Cottage at Massies Mill & the Blue Ridge Mountains

Virginia / Massies Mill

Massies Mill cottage

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$171

Responds fast!
avg. 2 hours 40 minutes

Price per night from

$171

Great rentals within 20 miles that match your search

Distance approx 17.43 km from Massies Mill

(12) Excellent 

22

Blueberry Hill Farm in Historic Shenandoah Valley

Virginia / Staunton

Staunton apartment

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Car not necessary
  • Air conditioning
“Excellent "headquarter" for exploring Shenandoah” We stayed for a week and was very satisfied with both location and the room and its facilities. Their was always a nice place to sit outside and enjoy the landscape or read regardless of the weather -
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Price per night from

$103

Price per night from

$103

Distance approx 18.12 km from Massies Mill

(1) Excellent 

32

Shenandoah Valley Farmhouse

Virginia / Waynesboro

Waynesboro house

4 9 3 nights min

  • 4 bedrooms
  • sleeps 9
  • 3 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$285

Price per night from

$285

Distance approx 9.75 km from Massies Mill

(7) Very Good 

30

Pet Friendly 2BR House in Blue Ridge Mtns, Close to Blue Ridge Parkway

Virginia / Lyndhurst

Lyndhurst house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 21 mi
  • Swimming pool
  • Child Friendly
“Cute and relaxing getaway” The cabin had such character and was extremely comfortable to stay in with a small kitchen, sufficient to meet the needs of a long weekend or week, two grill areas, and very relaxing. It is a ture log cabin in that there re
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Price per night from

$171

Responds fast!
avg. 2 hours 25 minutes

Price per night from

$171

Distance approx 9.48 km from Massies Mill

(10) Excellent 

11

Three Sisters Log Cabin

Virginia / Montebello

Montebello house

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$177

Price per night from

$177

Distance approx 9.72 km from Massies Mill

23

Ski-in/Ski-out Wintergreen House w/ Hot Tub!

Virginia / Wintergreen

Wintergreen house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$217

Responds fast!
avg. 9 minutes

Price per night from

$217

Distance approx 8.22 km from Massies Mill Show on Map

(5) Excellent 

26

Romantic, Pet-Friendly Cabin in Blue Ridge Mountains - Barnwood

Virginia / Tyro

Tyro log cabin

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child Friendly
“Peaceful and Beautiful” My husband, 8 month old son, and I took our best friend for a weekend of relaxation before she left to go into some difficult and strenuous work for the summer. It was the perfect place for us all to go. The house was adorable
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Price per night from

$147

Responds fast!
avg. 2 hours 25 minutes

Price per night from

$147

Distance approx 10.08 km from Massies Mill

(1) Excellent 

10

Cozy and Clean Resort Condo - New Ownership and listed for the first time!

Virginia / Wintergreen

Wintergreen condo

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 265 mi
  • Ski
  • Child Friendly

Price per night from

$102

Price per night from

$102

Distance approx 5.93 km from Massies Mill Show on Map

(2) Excellent 

22

Escape to Campbell's Creek

Virginia / Tyro

Tyro log cabin

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly

Price per night from

$287

Price per night from

$287

Distance approx 9.66 km from Massies Mill

13

Rock-n-Creek Cabin mile post 27 off BR Pkwy

Virginia / Montebello

Montebello log cabin

3 11 2 nights min

  • 3 bedrooms
  • sleeps 11
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$223

Price per night from

$223

Distance approx 7.94 km from Massies Mill Show on Map

(10) Very Good 

28

Peaceful Seclusion in The Blue Ridge,Pet friendly

Virginia / Lovingston

Lovingston log cabin

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 322 mi
  • Child Friendly
  • Air conditioning
“Absolutely perfect!” This cabin is adorable! The setting is completely secluded and was the perfect spot for my family to stay as I graduated from Liberty University this past weekend. My boys were able to run and be loud and loved cooking their own
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Price per night from

$170

Price per night from

$170

Distance approx 10.19 km from Massies Mill

(3) Very Good 

16

Down On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities

Virginia / Wintergreen

Wintergreen condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$114

Price per night from

$114

Distance approx 12.6 km from Massies Mill

(1) Excellent 

25

Lyndhurst Log Cabin on Farm w/Pond+Stocked Stream!

Virginia / Lyndhurst

Lyndhurst log cabin

1 6 min stay varies

  • 1 bedroom
  • sleeps 6
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$171

Responds fast!
avg. 9 minutes

Price per night from

$171

Distance approx 10.89 km from Massies Mill

(21) Excellent 

46

Simple Pleasures -N Ridge - Holidays Upon Us

Virginia / Wintergreen

Wintergreen apartment

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ski
“Wonderful” The accommodations beautiful, Simple Pleasures North Ridge Holidays Upon Us, great location, good food, great skiing for grandkids [first time], son and wife. I would definitely recommend this rental to anyone; it was absolutely stocked w
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Price per night from

$172

Responds fast!
avg. 1 hour 36 minutes

Price per night from

$172

Distance approx 14.38 km from Massies Mill

8

Luxury Yurt in the Blue Ridge Mountains of Virginia Near Wintergreen

Virginia / Afton

Afton yurt

1 5 2 nights min

  • 1 bedroom
  • sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation

Price per night from

$172

Price per night from

$172

Distance approx 9.77 km from Massies Mill

(4) Excellent 

19

Pet Friendly Virginia Blue Ridge Mountain Cabin Rental-Foxwood

Virginia / Wintergreen

Wintergreen house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child Friendly
“Great mountain getaway!” Conveneintly located near Wintergreen Resort, this is an awesome way to enjoy snowboarding and sking. The cabins are quaint and cozy and the owners are very nice. Especially their Jack Russell Toby! He visits every cabin eve
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Price per night from

$170

Responds fast!
avg. 2 hours 25 minutes

Price per night from

$170

Distance approx 10.91 km from Massies Mill

(7) Excellent 

13

Christmas Available: Luxury Mountain House w/ Resort Membership

Virginia / Wintergreen

Wintergreen house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Mountain Resort in Va” Cozy ski getaway or family retreat. Soaring wood ceilings and stone fireplace; huge windows. Lovely views of lush green lawn and several tall trees. Peaceful and quiet. Huge kitchen and dining area, full amenites, and very clean
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Price per night from

$303

Responds fast!
avg. 2 hours 59 minutes

Price per night from

$303

Distance approx 9.63 km from Massies Mill

17

Mountain Escape in the Spring

Virginia / Wintergreen

Wintergreen apartment

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$126

Responds fast!
avg. 2 hours 16 minutes

Price per night from

$126

Distance approx 9.8 km from Massies Mill

25

Wintergreen Studio w/ 4th of July Fireworks Views!

Virginia / Wintergreen

Wintergreen studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$97

Responds fast!
avg. 9 minutes

Price per night from

$97

Distance approx 9.27 km from Massies Mill

22

Dogwood Haven

Virginia / Wintergreen

Wintergreen apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$171

Price per night from

$171

Distance approx 15.25 km from Massies Mill

(3) Excellent 

17

Rose Cottage at Steeles Tavern

Virginia / Lexington

Lexington house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$184

Responds fast!
avg. 2 hours 57 minutes

Price per night from

$184

Distance approx 19.18 km from Massies Mill

(24) Excellent 

21

Afton Cottage: UVA, Monticello, Hiking, Wineries, Breweries.

Virginia / Charlottesville

Charlottesville cottage

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Great at-home feel” This is a great place in the quiet of the country, birds (and squirrels) in the birdfeeders on the porch, hawks (and buzzards) overhead, and sometimes deer grazing in the back yard. A lovely retreat in the woods but close to Charlo
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Price per night from

$252

Price per night from

$252

Distance approx 10.14 km from Massies Mill

(3) Very Good 

19

2BR Walkout Condo Private and Cozy!

Virginia / Wintergreen

Wintergreen apartment

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$137

Responds fast!
avg. 1 hour 13 minutes

Price per night from

$137

Distance approx 9.68 km from Massies Mill

(5) Excellent 

Certificate of Excellence

15

TREELOFT- in the snow drift!

Virginia / Wintergreen

Wintergreen house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly

Certificate of Excellence

Price per night from

$446

Responds fast!
avg. 12 minutes

Price per night from

$446

Distance approx 10.9 km from Massies Mill

(1) Excellent 

21

The Retreat at Wintergreen

Virginia / Wintergreen

Wintergreen house

4 12 3 nights min

  • 4 bedrooms
  • sleeps 12
  • 3 nights min
  • Ski
  • Child Friendly
  • Private garden

Price per night from

$451

Price per night from

$451

Distance approx 10.8 km from Massies Mill

(1) Average 

24

Peaceful Roseland House w/ Loft, Deck & Mtn Views!

Virginia / Wintergreen

Wintergreen house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$325

Responds fast!
avg. 9 minutes

Price per night from

$325

Distance approx 9.09 km from Massies Mill

(10) Excellent 

68

Fit for a KING ( king size beds!)

Virginia / Wintergreen

Wintergreen house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
“Great!” The process of reserving, paying, getting in the house and out of the house was easy and fool-proof!! The house was amazing and the location was perfect. Dawn (the contact for the house) was the most helpful and thoughtful person you could
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Price per night from

$561

Responds fast!
avg. 12 minutes

Price per night from

$561

Distance approx 10.73 km from Massies Mill

(2) Excellent 

24

Chestnut Place Mountain Lodge

Virginia / Wintergreen

Wintergreen house

5 15 min stay varies

  • 5 bedrooms
  • sleeps 15
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$628

Responds fast!
avg. 12 minutes

Price per night from

$628

Distance approx 19.49 km from Massies Mill

18

Experience small-town life in the Blue Ridge Mountains

Virginia / Buena Vista

Buena Vista room

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child Friendly

Price per night from

$102

Price per night from

$102

Distance approx 9.85 km from Massies Mill

(10) Excellent 

41

CRAZY AMAZING get-a-way! (Crazy, in a GOOD way)

Virginia / Wintergreen

Wintergreen house

5 13 min stay varies

  • 5 bedrooms
  • sleeps 13
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$676

Responds fast!
avg. 12 minutes

Price per night from

$676

Distance approx 19.26 km from Massies Mill

(1) Excellent 

24

Maren Estate (Mountain Estate 20 min to UVA)

Virginia / Afton

Afton house

6 14 3 nights min

  • 6 bedrooms
  • sleeps 14
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$1,939

Price per night from

$1,939

Distance approx 18.96 km from Massies Mill

64

The Inn at Blue Mountain Brewery

Virginia / Afton

Afton house

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly

Price per night from

$797

Price per night from

$797

Distance approx 10.63 km from Massies Mill

9

Mountain Retreat

Virginia / Wintergreen

Wintergreen house

5 8 min stay varies

  • 5 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly

Price per night from

$399

Price per night from

$399

Distance approx 16.04 km from Massies Mill

26

❤The Blue HummingBird❤9acre Nature's Hideaway❤Farm Country Getaway❤

Virginia / Staunton

Staunton house

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$142

Price per night from

$142

Distance approx 7.14 km from Massies Mill Show on Map

21

Lovingston Get-Away

Virginia / Lovingston

Lovingston apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

Price per night from

$114

Price per night from

$114

Distance approx 9.61 km from Massies Mill

(26) Excellent 

17

WINTERGREEN MOUNTAIN HOUSE

Virginia / Wintergreen

Wintergreen house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Ski
  • Child Friendly

Price per night from

$228

Responds fast!
avg. 1 hour 10 minutes

Price per night from

$228

Distance approx 9.94 km from Massies Mill

(10) Excellent 

24

Top of the Resort (Discounted Rates Available)

Virginia / Wintergreen

Wintergreen house

6 14 2 nights min

  • 6 bedrooms
  • sleeps 14
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$329

Price per night from

$329

Distance approx 10.15 km from Massies Mill

(3) Very Good 

7

Beautiful Home and Best Value at Wintergreen

Virginia / Roseland

Roseland townhouse

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$430

Price per night from

$430