Holiday rentals near Cross Keys Vineyards
We found 810 holiday rentals — enter your dates for availability
Choose the perfect holiday home within easy reach of Cross Keys Vineyards. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Cross Keys Vineyards
Showing deals for:1 Aug - 8 Aug
Image gallery for Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub!
1010 out of 10 rating
Exceptional
(6 reviews)
Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub!
Waynesboro, VA
8% off
Price is NZ$18,278
NZ$18,278
NZ$2,611 per night
includes taxes & fees
Image gallery for Hawks Nest · Mountain Top Cabin w/ Amazing Views, Coffee, Games
9.89.8 out of 10 rating
Exceptional
(23 reviews)
Hawks Nest · Mountain Top Cabin w/ Amazing Views, Coffee, Games
Free Union, VA
13% off
Price is NZ$6,169
NZ$6,169
NZ$881 per night
includes taxes & fees
Image gallery for 5BR Private Mountain Game Cabin! Hot Tub, Fire Pit
9.89.8 out of 10 rating
Exceptional
(9 reviews)
5BR Private Mountain Game Cabin! Hot Tub, Fire Pit
McGaheysville, VA
8% off
Price is NZ$9,018
NZ$9,018
NZ$1,288 per night
includes taxes & fees
Image gallery for Summer Fun Includes Free Outdoor Pool
1010 out of 10 rating
Exceptional
(32 reviews)
Summer Fun Includes Free Outdoor Pool
McGaheysville, VA
8% off
Price is NZ$6,808
NZ$6,808
NZ$973 per night
includes taxes & fees
Image gallery for Mt Views - Sauna - Hot Tub - Adulting - Game Room
1010 out of 10 rating
Exceptional
(12 reviews)
Mt Views - Sauna - Hot Tub - Adulting - Game Room
McGaheysville, VA
12% off
Price is NZ$6,552
NZ$6,552
NZ$936 per night
includes taxes & fees
Image gallery for New 6 bedroom Massanutten home with 3 king beds steps from all the attractions
1010 out of 10 rating
Exceptional
(47 reviews)
New 6 bedroom Massanutten home with 3 king beds steps from all the attractions
McGaheysville, VA
8% off
Price is NZ$8,343
NZ$8,343
NZ$1,192 per night
includes taxes & fees
Image gallery for Epic ~ Game Room, Hot Tub, Firepit, BBQ ~ 7 min to Shenandoah National Park
1010 out of 10 rating
Exceptional
(5 reviews)
Epic ~ Game Room, Hot Tub, Firepit, BBQ ~ 7 min to Shenandoah National Park
Elkton, VA
12% off
Price is NZ$6,928
NZ$6,928
NZ$990 per night
includes taxes & fees
Image gallery for Cozy 5 BR Family Getaway with Hot Tub, Game Room, Sauna, Level 2 EV Charger!
1010 out of 10 rating
Exceptional
(13 reviews)
Cozy 5 BR Family Getaway with Hot Tub, Game Room, Sauna, Level 2 EV Charger!
McGaheysville, VA
8% off
Price is NZ$6,775
NZ$6,775
NZ$968 per night
includes taxes & fees
Image gallery for Hidden Haven - Kids friendly home, Great Location, Extended Deck, Outdoor Dining
1010 out of 10 rating
Exceptional
(28 reviews)
Hidden Haven - Kids friendly home, Great Location, Extended Deck, Outdoor Dining
McGaheysville, VA
8% off
Price is NZ$6,701
NZ$6,701
NZ$957 per night
includes taxes & fees
Image gallery for Hot Tub - Massage Chair - Game Room - Fenced Yard
1010 out of 10 rating
Exceptional
(42 reviews)
Hot Tub - Massage Chair - Game Room - Fenced Yard
McGaheysville, VA
8% off
Price is NZ$7,048
NZ$7,048
NZ$1,007 per night
includes taxes & fees
Image gallery for Relax and get away in the tree tops in our Eagle's Nest Tree House
1010 out of 10 rating
Exceptional
(21 reviews)
Relax and get away in the tree tops in our Eagle's Nest Tree House
Shenandoah, VA
8% off
Price is NZ$3,912
NZ$3,912
NZ$559 per night
includes taxes & fees
Image gallery for KinStay Massanutten Family Cabin-Time with Family, Shuffleboard, Mountain Views
1010 out of 10 rating
Exceptional
(95 reviews)
KinStay Massanutten Family Cabin-Time with Family, Shuffleboard, Mountain Views
McGaheysville, VA
8% off
Price is NZ$5,999
NZ$5,999
NZ$857 per night
includes taxes & fees
Image gallery for Whimsical Hobbit House in the Shenandoah Virginia "Shire"
1010 out of 10 rating
Exceptional
(69 reviews)
Whimsical Hobbit House in the Shenandoah Virginia "Shire"
Shenandoah, VA
8% off
Price is NZ$3,876
NZ$3,876
NZ$554 per night
includes taxes & fees
Image gallery for Trail's End at Massanutten Resort
1010 out of 10 rating
Exceptional
(12 reviews)
Trail's End at Massanutten Resort
McGaheysville, VA
12% off
Price is NZ$3,158
NZ$3,158
NZ$451 per night
includes taxes & fees
Image gallery for The Great Adventure
1010 out of 10 rating
Exceptional
(19 reviews)
The Great Adventure
McGaheysville, VA
12% off
Price is NZ$4,147
NZ$4,147
NZ$592 per night
includes taxes & fees
Image gallery for "The Sparrow" at Historic Downtown Staunton
9.89.8 out of 10 rating
Exceptional
(13 reviews)
"The Sparrow" at Historic Downtown Staunton
Staunton, VA
8% off
Price is NZ$3,718
NZ$3,718
NZ$531 per night
includes taxes & fees
Image gallery for Peaceful mountain farmhouse, close to Shenandoah NP, wineries and more
1010 out of 10 rating
Exceptional
(28 reviews)
Peaceful mountain farmhouse, close to Shenandoah NP, wineries and more
Stanardsville, VA
7% off
Price is NZ$3,188
NZ$3,188
NZ$455 per night
includes taxes & fees
Image gallery for The Haven, located in the heart of the Shenandoah Valley
1010 out of 10 rating
Exceptional
(13 reviews)
The Haven, located in the heart of the Shenandoah Valley
Waynesboro, VA
8% off
Price is NZ$3,529
NZ$3,529
NZ$504 per night
includes taxes & fees
Image gallery for Feel At Home Away From Home in Our Comfortable 3 Bed., 2 Bath. House!
1010 out of 10 rating
Exceptional
(83 reviews)
Feel At Home Away From Home in Our Comfortable 3 Bed., 2 Bath. House!
McGaheysville, VA
20% off
Price is NZ$2,898
NZ$2,898
NZ$414 per night
includes taxes & fees
Image gallery for Spacious craftsman home in downtown Staunton Virginia
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Spacious craftsman home in downtown Staunton Virginia
Staunton, VA
15% off
Price is NZ$4,504
NZ$4,504
NZ$643 per night
includes taxes & fees
Image gallery for Whole House Sleeps 6
1010 out of 10 rating
Exceptional
(24 reviews)
Whole House Sleeps 6
Harrisonburg, VA
34% off
Price is NZ$6,904
NZ$6,904
NZ$986 per night
includes taxes & fees
Image gallery for The Cozy Suite - Walking Distance to Downtown Harrisonburg and JMU
9.89.8 out of 10 rating
Exceptional
(45 reviews)
The Cozy Suite - Walking Distance to Downtown Harrisonburg and JMU
Harrisonburg, VA
8% off
Price is NZ$1,634
NZ$1,634
NZ$233 per night
includes taxes & fees
Image gallery for Beautiful family home about 3 minutes from most resort activities (pet friendly)
1010 out of 10 rating
Exceptional
(31 reviews)
Beautiful family home about 3 minutes from most resort activities (pet friendly)
McGaheysville, VA
8% off
Price is NZ$4,308
NZ$4,308
NZ$615 per night
includes taxes & fees
Image gallery for Skylight House at Massanutten with game room, newly renovated
9.49.4 out of 10 rating
Exceptional
(26 reviews)
Skylight House at Massanutten with game room, newly renovated
McGaheysville, VA
8% off
Price is NZ$3,995
NZ$3,995
NZ$571 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Cross Keys Vineyards
Peaceful Getaway-Hot Tub, Fire Pit, PS5, Amazing Views!
Sleeps 6 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Massanutten Near Slopes, 2 Masters, Pool Table, Air Hockey, 2 FPs
Sleeps 12 · 4 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
310 reviews(310 reviews)
The Summit at Massanutten Resort by Tripforth
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
57 reviews(57 reviews)
Newly-built in Massanutten Resort Prime Area, Pool Table, Six Smart TVs, Gas FP
Sleeps 10 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
170 reviews(170 reviews)
Hawk Mountain Song- Massanutten Home with Private Hot tub! NEW- Pet Friendly!
Sleeps 10 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
58 reviews(58 reviews)
Massanutten Resort log home -slope & unobstructed mountain views-FREE POOL PASS!
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
65 reviews(65 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value