Holiday rentals near Whiskey Point Trailhead
We found 1,434 holiday rentals — enter your dates for availability
Choose the right holiday home within easy reach of Whiskey Point Trailhead. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as a garden and pool. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Whiskey Point Trailhead
Showing deals for:19 Sept - 26 Sept
Image gallery for Maple Terrace -Mt Washington -15 steps to Grandview Ave. and the amazing views!
9.89.8 out of 10 rating
Exceptional
(62 reviews)
Maple Terrace -Mt Washington -15 steps to Grandview Ave. and the amazing views!
Pittsburgh, PA
8% off
Price is AU$2,137
AU$2,137
AU$305 per night
includes taxes & fees
Image gallery for FIVE STARS! For SPORTS, THEATER, STADIUMS, CASINO, RESERVED PARKING, A/C COMFORT
9.89.8 out of 10 rating
Exceptional
(56 reviews)
FIVE STARS! For SPORTS, THEATER, STADIUMS, CASINO, RESERVED PARKING, A/C COMFORT
Pittsburgh, PA
12% off
Price is AU$4,286
AU$4,286
AU$612 per night
includes taxes & fees
Image gallery for Offering 50 % discounts on stays of 28 days or more!! 10% on 7 or more days!
1010 out of 10 rating
Exceptional
(12 reviews)
Offering 50 % discounts on stays of 28 days or more!! 10% on 7 or more days!
Pittsburgh, PA
11% off
Price is AU$2,501
AU$2,501
AU$357 per night
includes taxes & fees
Image gallery for Stunning & Newest 100+ year old Historic Victorian
9.49.4 out of 10 rating
Exceptional
(20 reviews)
Stunning & Newest 100+ year old Historic Victorian
Pittsburgh, Pennsylvania
12% off
Price is AU$6,620
AU$6,620
AU$946 per night
includes taxes & fees
Image gallery for CLEAN, COMFORTABLE, CONVENIENT, PRIVATE CAR PARK & DISCOUNTS FOR WEEKLY RENTALS
9.89.8 out of 10 rating
Exceptional
(128 reviews)
CLEAN, COMFORTABLE, CONVENIENT, PRIVATE CAR PARK & DISCOUNTS FOR WEEKLY RENTALS
Pittsburgh, PA
12% off
Price is AU$4,709
AU$4,709
AU$673 per night
includes taxes & fees
Image gallery for Unique- Spacious- Highland Park-2 king- Quiet - BBQ- Free Street Parking
1010 out of 10 rating
Exceptional
(19 reviews)
Unique- Spacious- Highland Park-2 king- Quiet - BBQ- Free Street Parking
Pittsburgh, PA
11% off
Price is AU$2,454
AU$2,454
AU$351 per night
includes taxes & fees
Image gallery for Craftsman Charmer | Easy Access to City & Airport
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Craftsman Charmer | Easy Access to City & Airport
Pittsburgh, PA
8% off
Price is AU$2,002
AU$2,002
AU$286 per night
includes taxes & fees
Image gallery for 2 Bedroom/ 2 Bath- 5 mins to stadiums - BEST city views - Free parking!
9.69.6 out of 10 rating
Exceptional
(48 reviews)
2 Bedroom/ 2 Bath- 5 mins to stadiums - BEST city views - Free parking!
Pittsburgh, PA
15% off
Price is AU$2,612
AU$2,612
AU$373 per night
includes taxes & fees
Image gallery for Lovely 1 bedroom rental unit that sleeps 4 adults
1010 out of 10 rating
Exceptional
(6 reviews)
Lovely 1 bedroom rental unit that sleeps 4 adults
Wilmerding, PA
7% off
Price is AU$1,386
AU$1,386
AU$198 per night
includes taxes & fees
Image gallery for *New* Loft 3 min to CMU, Pitt Sleeps 4
9.89.8 out of 10 rating
Exceptional
(10 reviews)
*New* Loft 3 min to CMU, Pitt Sleeps 4
Pittsburgh, Pennsylvania
8% off
Price is AU$1,585
AU$1,585
AU$226 per night
includes taxes & fees
Image gallery for PGH Jewel - Modern All New 5B/5B, Near Downtown, Private Parking
1010 out of 10 rating
Exceptional
(13 reviews)
PGH Jewel - Modern All New 5B/5B, Near Downtown, Private Parking
Pittsburgh, PA
7% off
Price is AU$4,611
AU$4,611
AU$659 per night
includes taxes & fees
Image gallery for Updated Victorian - Serene Backyard + City Access
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Updated Victorian - Serene Backyard + City Access
Pittsburgh, PA
8% off
Price is AU$2,616
AU$2,616
AU$374 per night
includes taxes & fees
Image gallery for California Ave Quarters-2 Bedroom w/ Easy Parking!
1010 out of 10 rating
Exceptional
(5 reviews)
California Ave Quarters-2 Bedroom w/ Easy Parking!
Pittsburgh, Pennsylvania
8% off
Price is AU$1,275
AU$1,275
AU$182 per night
includes taxes & fees
Image gallery for Fun 4 BR 2 bath FULL renovated house w/ driveway
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Fun 4 BR 2 bath FULL renovated house w/ driveway
Pittsburgh, PA
14% off
Price is AU$3,295
AU$3,295
AU$471 per night
includes taxes & fees
Image gallery for Modern Spacious Home • Rooftop Deck
1010 out of 10 rating
Exceptional
(23 reviews)
Modern Spacious Home • Rooftop Deck
Pittsburgh, PA
16% off
Price is AU$8,907
AU$8,907
AU$1,272 per night
includes taxes & fees
Image gallery for Amazingly Homey w/Garage + Outdoor Space! 5B/2B
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Amazingly Homey w/Garage + Outdoor Space! 5B/2B
Pittsburgh, PA
7% off
Price is AU$6,388
AU$6,388
AU$913 per night
includes taxes & fees
Image gallery for Unbeatable Location - Walkable Entertainment
1010 out of 10 rating
Exceptional
(5 reviews)
Unbeatable Location - Walkable Entertainment
Pittsburgh, PA
20% off
Price is AU$2,306
AU$2,306
AU$329 per night
includes taxes & fees
Image gallery for Modern & Cozy Getaway-Walk to Scenic Overlooks
9.69.6 out of 10 rating
Exceptional
(22 reviews)
Modern & Cozy Getaway-Walk to Scenic Overlooks
Pittsburgh, PA
8% off
Price is AU$3,974
AU$3,974
AU$568 per night
includes taxes & fees
Image gallery for Fantastic 5 BR w/4x Off Street Parking - Sleeps 16
9.09.0 out of 10 rating
Wonderful
(12 reviews)
Fantastic 5 BR w/4x Off Street Parking - Sleeps 16
Pittsburgh, PA
7% off
Price is AU$7,248
AU$7,248
AU$1,035 per night
includes taxes & fees
Image gallery for Free Coupon Pkg Deal! Inclination Vacation: Luxe 5BR Home, 10 mins to Downtown
1010 out of 10 rating
Exceptional
(9 reviews)
Free Coupon Pkg Deal! Inclination Vacation: Luxe 5BR Home, 10 mins to Downtown
Pittsburgh, PA
12% off
Price is AU$5,809
AU$5,809
AU$830 per night
includes taxes & fees
Image gallery for Spacious cozy retreat, off the beaten path close to all Pittsburgh attractions
8.48.4 out of 10 rating
Very good
(5 reviews)
Spacious cozy retreat, off the beaten path close to all Pittsburgh attractions
Cheswick, PA
8% off
Price is AU$3,133
AU$3,133
AU$448 per night
includes taxes & fees
Image gallery for Skyline Haven:5BR/3.5BA + Garage Parking + Rooftop
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Skyline Haven:5BR/3.5BA + Garage Parking + Rooftop
Pittsburgh, PA
7% off
Price is AU$10,615
AU$10,615
AU$1,516 per night
includes taxes & fees
Image gallery for Strip District Studio - Convenient to all Pittsburgh has to offer
9.69.6 out of 10 rating
Exceptional
(22 reviews)
Strip District Studio - Convenient to all Pittsburgh has to offer
Pittsburgh, PA
8% off
Price is AU$2,197
AU$2,197
AU$314 per night
includes taxes & fees
Image gallery for Amazing Mount Washington house 9 min to downtown
9.89.8 out of 10 rating
Exceptional
(32 reviews)
Amazing Mount Washington house 9 min to downtown
Pittsburgh, PA
14% off
Price is AU$3,202
AU$3,202
AU$457 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Whiskey Point Trailhead
Showing deals for: 19 Sept - 22 Sept
Stay Pittsburgh
Sleeps 4 · 2 bedrooms
7.67.6 out of 10
Goodgood
142 reviews(142 reviews)
The current price is AU$960
AU$960
for 3 nights, 1 room
AU$320 per night
includes taxes & fees
The Maverick by Kasa
Sleeps 2 · 1 bedroom
8.88.8 out of 10
Excellentexcellent
659 reviews(659 reviews)
The current price is AU$988
AU$988
for 3 nights, 1 room
AU$329 per night
includes taxes & fees
Peaceful Treetop Living 10 min. to downtown/ stadium, large deck, pet friendly
Sleeps 3 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
The current price is AU$868
AU$868
for 3 nights, 1 apartment
AU$289 per night
includes taxes & fees
Placemakr Downtown Pittsburgh
Sleeps 6 · 2 bedrooms
9.49.4 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
The current price is AU$1,928
AU$1,928
for 3 nights, 1 apartment
AU$643 per night
includes taxes & fees
Not so tiny house with full kitchen & patio swing
Sleeps 3 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
The current price is AU$1,088
AU$1,088
for 3 nights, 1 home
AU$363 per night
includes taxes & fees
Kasa South Side Pittsburgh
Sleeps 5 · 2 bedrooms
8.48.4 out of 10
Very goodvery good
86 reviews(86 reviews)
The current price is AU$774
AU$774
for 3 nights, 1 room
AU$258 per night
includes taxes & fees
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