Middletown Vacation Rentals | Book Now, Save Up to 30%

All in pricing: Taxes and fees included

Save $152

Preferred host

Entire home in Strasburg, VA

Dec 3 - 6

$264/night

5.0

4

2 bedrooms

4 guests

$1,017$864total

Save $61

Preferred host

Entire home in Front Royal, VA

Nov 17 - 20

$216/night

4.7

3

1 bedroom

4 guests

$767$706total

Save $207

Preferred host

House in Winchester, VA

Nov 25 - 28

$256/night

4.7

28

2 bedrooms

10 guests

$1,007$800total

Save $110

Preferred host

House in Winchester, VA

Nov 17 - 20

$192/night

4.6

51

3 bedrooms

12 guests

$706$596total

Save $54

Preferred host

Entire home in Star Tannery, VA

Nov 17 - 20

$191/night

5.0

1

2 bedrooms

4 guests

$679$625total

Save $35

Preferred host

Entire home in Front Royal, VA

Dec 13 - 16

$123/night

5.0

7

2 bedrooms

4 guests

$441$406total

Save $63

Preferred host

Entire home in Front Royal, VA

Mar 15 - 18

$221/night

4.8

5

2 bedrooms

4 guests

Pay only $84 today

$792$729total

Save $91

Preferred host

Entire home in Front Royal, VA

Mar 3 - 6

$316/night

5.0

2

3 bedrooms

6 guests

Pay only $120 today

$1,132$1,041total

Save $181

Preferred host

Cabin in Maurertown, VA

Jan 2 - 5

$350/night

4.5

6

2 bedrooms

4 guests

$1,355$1,174total

Save $152

Guests rave

Entire cabin in Maurertown, VA

Nov 28 - Dec 1

$248/night

4.9

153

2 bedrooms

4 guests

$965$813total

Save $48

Preferred host

Townhouse in Winchester, VA

Nov 30 - Dec 3

$169/night

4.6

8

3 bedrooms

5 guests

$601$553total

Save $261

Guests rave

Entire vacation home in Linden, VA

Nov 17 - 20

$285/night

5.0

290

3 bedrooms

6 guests

$1,199$938total

Save $117

Preferred host

Entire home in Front Royal, VA

Nov 17 - 20

$410/night

4.9

16

3 bedrooms

6 guests

$1,458$1,341total

Save $208

Preferred host

Entire home in Maurertown, VA

Nov 17 - 20

$404/night

4.7

10

6 bedrooms

12 guests

$1,530$1,322total

Save $374

Preferred host

House in Shenandoah Farms, VA

Nov 29 - Dec 2

$181/night

4.8

265

2 bedrooms

4 guests

$958$584total

Save $140

Whimstay gem

Tiny home in Linden, VA

Dec 7 - 10

$230/night

5.0

55

1 bedroom

2 guests

$897$757total

Save $54

Preferred host

House in Shenandoah Farms, VA

Nov 17 - 20

$193/night

4.9

15

3 bedrooms

8 guests

$677$622total

Save $41

Preferred host

House in Fauquier County, VA

Nov 17 - 20

$143/night

4.7

41

2 bedrooms

5 guests

$510$469total

Save $127

Whimstay gem

Cabin in Luray, VA

Nov 17 - 20

$193/night

4.9

118

1 bedroom

4 guests

$764$636total

Save $701

Whimstay gem

Loft in Luray, VA

Nov 18 - 21

$297/night

4.9

204

1 bedroom

2 guests

$1,691$990total

Save $143

Whimstay gem

Cabin in Luray, VA

Nov 22 - 25

$237/night

4.9

203

1 bedroom

2 guests

$927$785total

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Map shows last minute vacation rentals in Middletown