Middlebrook Rentals

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72 Houses

25

FABULOUS FARM GETAWAY

Virginia / Middlebrook

Middlebrook cottage

4 15 1 night min

  • 4 bedrooms
  • sleeps 15
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$150

Price per night from

$150

13

Mountain Pond House

Virginia / Middlebrook

Middlebrook guest house

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$155

Price per night from

$155

Great rentals within 20 miles that match your search

Distance approx 17.93 km from Middlebrook

(4) Very Good 

8

Spacious house located in Shenandoah Valley

Virginia / Waynesboro

Waynesboro house

4 6 2 nights min

  • 4 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 338 mi
  • Child Friendly
  • Car not necessary

Price per night from

$90

Price per night from

$90

Distance approx 17.96 km from Middlebrook

(1) Excellent 

39

Central Wintergreen Home - 70 Steps to Ski Slopes!

Virginia / Wintergreen

Wintergreen house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$344

Responds fast!
avg. 1 hour 2 minutes

Price per night from

$344

Distance approx 13.22 km from Middlebrook

(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

$249

Price per night from

$249

Distance approx 15.37 km from Middlebrook

(4) Very Good 

23

Pet-Friendly Secluded Mountain Cabin by Pool - Rockwood

Virginia / Staunton

Staunton log cabin

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child Friendly
“Great place to stay close to Blue Ridge Parkway” This is a nice quiet place to stay that is just a couple minutes down the hill from the Blue Ridge Parkway.
…see more

Price per night from

$129

Responds fast!
avg. 2 hours 51 minutes

Price per night from

$129

Distance approx 13 km from Middlebrook

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

$194

Price per night from

$194

Distance approx 19.7 km from Middlebrook

(27) Very Good 

21

Willow Haven - 1800's Log Cabin

Virginia / Lexington

Lexington log cabin

5 16 3 nights min

  • 5 bedrooms
  • sleeps 16
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Excellent” It was beyond perfect. Peaceful. Great location to town. Easy to get to yet with no neighbors! Can't wait to go back!
…see more

Price per night from

$383

Price per night from

$383

Distance approx 15.92 km from Middlebrook

13

The Mountain Outpost

Virginia / Vesuvius

Vesuvius house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly

Price per night from

$174

Responds fast!
avg. 1 hour 57 minutes

Price per night from

$174

Distance approx 17.23 km from Middlebrook

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

$110

Responds fast!
avg. 2 hours 28 minutes

Price per night from

$110

Distance approx 17.9 km from Middlebrook

(3) Very Good 

16

Tyro Slope-Side House Ski In/Out Yr Rnd Views w/AC

Virginia / Wintergreen

Wintergreen house

3 8 2 nights min

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

Price per night from

$169

Price per night from

$169

Distance approx 18.34 km from Middlebrook

(13) Excellent 

18

2 bedroom Log cabins in Lexington VA, 2m from VHC, Rockbridge Co. Natural Bridge

Virginia / Lexington

Lexington log cabin

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Happy Thanksgiving!” It was a fabulous place to visit and spend the holiday!We all loved it! The cabin was so homey and cozy...it could not have been better!
…see more

Price per night from

$184

Price per night from

$184

Distance approx 16.66 km from Middlebrook

(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

$89

Price per night from

$89

Distance approx 18.17 km from Middlebrook

(6) Excellent 

8

Alone Mill Schoolhouse - Outdoor Lovers Paradise

Virginia / Lexington

Lexington house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“perfect place to relax” We had a wonderful time at the Alone Mill Schoolhouse. The house is charming and has everything you need for a great vacation. Charles and Sarah are very nice landlords. Thanks again for having us. We will definitely recommend
…see more

Price per night from

$184

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$184

Distance approx 16.65 km from Middlebrook

(2) Excellent 

22

3BR Wintergreen House w/Private Decks!

Virginia / Wintergreen

Wintergreen house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$184

Responds fast!
avg. 14 minutes

Price per night from

$184

Distance approx 16.76 km from Middlebrook

(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

$100

Price per night from

$100

Distance approx 15.34 km from Middlebrook

(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

$145

Responds fast!
avg. 14 minutes

Price per night from

$145

Distance approx 18.34 km from Middlebrook

30

Log Cabin, Lexington Virginia Shenandoah Valley Rockbridge County VA Horse Cente

Virginia / Lexington

Lexington log cabin

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$184

Price per night from

$184

Distance approx 17.46 km from Middlebrook

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

$85

Responds fast!
avg. 14 minutes

Price per night from

$85

Distance approx 17.53 km from Middlebrook

24

NEW! Cozy Wintergreen Resort Home - Walk to Lifts!

Virginia / Wintergreen

Wintergreen townhouse

2 5 min stay varies

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

Price per night from

$140

Responds fast!
avg. 9 minutes

Price per night from

$140

Distance approx 10.04 km from Middlebrook

(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

$159

Responds fast!
avg. 2 hours 57 minutes

Price per night from

$159

Distance approx 17.26 km from Middlebrook

(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

$547

Responds fast!
avg. 33 minutes

Price per night from

$547

Distance approx 16.85 km from Middlebrook

(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

$393

Responds fast!
avg. 1 hour 1 minutes

Price per night from

$393

Distance approx 16.68 km from Middlebrook

(16) Excellent 

Certificate of Excellence

20

The Bear Dance Cabin at Wintergreen

Virginia / Wintergreen

Wintergreen log cabin

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Very nice accomidations, close to resort & slopes” The cabin is adorable & cozy. Even though it has a cabin feel, the bathrooms and kitchen are very nice and you don't feel like you're "roughing it" at all. The place a newer build, so it feels very cl
…see more

Certificate of Excellence

Price per night from

$174

Responds fast!
avg. 1 hour 30 minutes

Price per night from

$174

Distance approx 16.46 km from Middlebrook

(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

$284

Responds fast!
avg. 1 hour 2 minutes

Price per night from

$284

Distance approx 15.52 km from Middlebrook

(4) Very Good 

26

Private Pet-Friendly 3BR Blue Ridge Mtn Cabin - Huge Deck

Virginia / Charlottesville

Charlottesville log cabin

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child Friendly
“Wonderful cabin on the Blue Ridge Parkway” Staying at this cabin was the highlight of the vacation for my kids. We shared it with my brother and his family and the kids had a wonderful time between the loft bedroom and the short hiking trail around t
…see more

Price per night from

$228

Responds fast!
avg. 2 hours 51 minutes

Price per night from

$228

Distance approx 17 km from Middlebrook

(9) 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

$587

Responds fast!
avg. 33 minutes

Price per night from

$587

Distance approx 16.96 km from Middlebrook

33

Cozy Custom Home in Wintergreen Resort Area!

Virginia / Wintergreen

Wintergreen house

3 10 min stay varies

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

Price per night from

$264

Responds fast!
avg. 1 hour 2 minutes

Price per night from

$264

Distance approx 19.58 km from Middlebrook

27

NEW! Spacious Lexington Condo 10 Min. to Downtown!

Virginia / Lexington

Lexington townhouse

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$155

Responds fast!
avg. 9 minutes

Price per night from

$155

Distance approx 17.11 km from Middlebrook

(1) Excellent 

32

A Cajun Chalet

Virginia / Wintergreen

Wintergreen house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$448

Responds fast!
avg. 34 minutes

Price per night from

$448

Distance approx 17.12 km from Middlebrook

24

NEW! Wintergreen Condo w/Views & Shuttle to Resort

Virginia / Wintergreen

Wintergreen condo

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$140

Responds fast!
avg. 14 minutes

Price per night from

$140

Distance approx 17.49 km from Middlebrook

(1) Excellent 

23

NEW! Cozy Wintergreen Resort Condo w/ Pool Access!

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

$110

Responds fast!
avg. 1 hour 2 minutes

Price per night from

$110

Distance approx 16.94 km from Middlebrook

24

NEW! Modern Wintergreen Farmhouse - 1 Mi to Resort

Virginia / Wintergreen

Wintergreen condo

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$249

Responds fast!
avg. 1 hour 2 minutes

Price per night from

$249

Distance approx 16.61 km from Middlebrook

19

Skogenhus - Wintergreen Vacation Rental

Virginia / Wintergreen

Wintergreen house

5 6 1 night min

  • 5 bedrooms
  • sleeps 6
  • 1 night min
  • Ski
  • Child Friendly
  • Private garden

Price per night from

$498

Price per night from

$498

Distance approx 16.79 km from Middlebrook

26

NEW! Wintergreen Home w/Deck & Community Amenities

Virginia / Wintergreen

Wintergreen house

3 10 min stay varies

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

Price per night from

$244

Responds fast!
avg. 1 hour 2 minutes

Price per night from

$244

Distance approx 16.57 km from Middlebrook

32

NEW! Chic Cabin w/Deck in Wintergreen Resort!

Virginia / Wintergreen

Wintergreen cottage

3 6 min stay varies

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

Price per night from

$161

Responds fast!
avg. 9 minutes

Price per night from

$161

Distance approx 18.02 km from Middlebrook

(25) Excellent 

17

WINTERGREEN MOUNTAIN HOUSE

Virginia / Wintergreen

Wintergreen house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$199

Responds fast!
avg. 1 hour 9 minutes

Price per night from

$199

Distance approx 18.06 km from Middlebrook

25

NEW! Wintergreen Cabin- Quiet Location Near Slopes

Virginia / Wintergreen

Wintergreen cottage

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$155

Responds fast!
avg. 14 minutes

Price per night from

$155