Holiday rentals near Underground Railroad Trail
We found 2,075 holiday rentals — enter your dates for availability
Choose the perfect private holiday rental within close proximity to Underground Railroad Trail. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as a hot tub and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Underground Railroad Trail
Showing deals for:14 Nov - 21 Nov
Image gallery for Chester County Oasis with Pool, Modern Ammenities, Tranquil and Private
1010 out of 10 rating
Exceptional
(6 reviews)
Chester County Oasis with Pool, Modern Ammenities, Tranquil and Private
West Chester, PA
8% off
Price is AU$4,453
AU$4,453
AU$636 per night
includes taxes & fees
Image gallery for Exceptional Downtown Townhome w/Roofdeck -4Bd/3Bth
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Exceptional Downtown Townhome w/Roofdeck -4Bd/3Bth
Philadelphia, PA
7% off
Price is AU$6,053
AU$6,053
AU$865 per night
includes taxes & fees
Image gallery for Idyllic 50 Acre Retreat w/ Pool, Tennis, Fishing; Built for XL Groups to Escape!
1010 out of 10 rating
Exceptional
(7 reviews)
Idyllic 50 Acre Retreat w/ Pool, Tennis, Fishing; Built for XL Groups to Escape!
Malvern, PA
8% off
Price is AU$18,577
AU$18,577
AU$2,654 per night
includes taxes & fees
Image gallery for Charming Glenolden House Near Airport & Philadelphia Eagles Stadium
9.29.2 out of 10 rating
Wonderful
(22 reviews)
Charming Glenolden House Near Airport & Philadelphia Eagles Stadium
Glenolden, PA
15% off
Price is AU$2,215
AU$2,215
AU$316 per night
includes taxes & fees
Image gallery for Lux Escape w/ Pool, Hot Tub & Sprawling Great Room - Built for XL Groups!
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Lux Escape w/ Pool, Hot Tub & Sprawling Great Room - Built for XL Groups!
Malvern, PA
8% off
Price is AU$15,639
AU$15,639
AU$2,234 per night
includes taxes & fees
Image gallery for Historic Kennett Square
9.29.2 out of 10 rating
Wonderful
(50 reviews)
Historic Kennett Square
Kennett Square, PA
12% off
Price is AU$2,839
AU$2,839
AU$406 per night
includes taxes & fees
Image gallery for Two-story condo in luxury townhouse. Free parking.
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Two-story condo in luxury townhouse. Free parking.
Wilmington, DE
10% off
Price is AU$3,021
AU$3,021
AU$432 per night
includes taxes & fees
Image gallery for Charming Carriage House in the Heart of Kennett
1010 out of 10 rating
Exceptional
(32 reviews)
Charming Carriage House in the Heart of Kennett
Kennett Square, PA
8% off
Price is AU$2,981
AU$2,981
AU$426 per night
includes taxes & fees
Image gallery for Comfy Tudor in suburban setting, 5mi from Center City Philadelphia. Coffee bar!
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Comfy Tudor in suburban setting, 5mi from Center City Philadelphia. Coffee bar!
Drexel Hill, PA
8% off
Price is AU$3,495
AU$3,495
AU$499 per night
includes taxes & fees
Image gallery for A2 @ Auberge
9.89.8 out of 10 rating
Exceptional
(13 reviews)
A2 @ Auberge
Ardmore, PA
8% off
Price is AU$2,739
AU$2,739
AU$391 per night
includes taxes & fees
Image gallery for 4 bed 2 bath,remodeled, private home in historic Chester Springs, Pet friendly.
9.89.8 out of 10 rating
Exceptional
(10 reviews)
4 bed 2 bath,remodeled, private home in historic Chester Springs, Pet friendly.
Chester Springs, PA
8% off
Price is AU$4,081
AU$4,081
AU$583 per night
includes taxes & fees
Image gallery for 4 Bedroom Home, Game Room & Pool in a Quiet Upscale Neighborhood
9.29.2 out of 10 rating
Wonderful
(7 reviews)
4 Bedroom Home, Game Room & Pool in a Quiet Upscale Neighborhood
Bryn Mawr, PA
9% off
Price is AU$19,020
AU$19,020
AU$2,717 per night
includes taxes & fees
Image gallery for Boat House on the Brandywine | Waterfront Cottage
1010 out of 10 rating
Exceptional
(25 reviews)
Boat House on the Brandywine | Waterfront Cottage
Downingtown, PA
9% off
Price is AU$1,939
AU$1,939
AU$277 per night
includes taxes & fees
Image gallery for 1 Bedroom x 1 Bath Suite in Malvern, PA
8.88.8 out of 10 rating
Excellent
(12 reviews)
1 Bedroom x 1 Bath Suite in Malvern, PA
Malvern, PA
8% off
Price is AU$1,735
AU$1,735
AU$248 per night
includes taxes & fees
Image gallery for Cozy Colonial Home in Drexel Hill
1010 out of 10 rating
Exceptional
(5 reviews)
Cozy Colonial Home in Drexel Hill
Drexel Hill, PA
6% off
Price is AU$4,063
AU$4,063
AU$580 per night
includes taxes & fees
Image gallery for Cozy 2-bedroom apartment with AC and WiFi in awesome Boothwyn
9.29.2 out of 10 rating
Wonderful
(11 reviews)
Cozy 2-bedroom apartment with AC and WiFi in awesome Boothwyn
Boothwyn, PA
8% off
Price is AU$1,993
AU$1,993
AU$285 per night
includes taxes & fees
Image gallery for Philadelphia Main Line Luxury Manor House in Villanova Pennsylvania
1010 out of 10 rating
Exceptional
(33 reviews)
Philadelphia Main Line Luxury Manor House in Villanova Pennsylvania
Villanova, PA
8% off
Price is AU$30,903
AU$30,903
AU$4,415 per night
includes taxes & fees
Image gallery for Farmhouse-Retreat Horses, Grapes & Orchards
1010 out of 10 rating
Exceptional
(23 reviews)
Farmhouse-Retreat Horses, Grapes & Orchards
Coatesville, PA
8% off
Price is AU$8,447
AU$8,447
AU$1,207 per night
includes taxes & fees
Image gallery for Cozy Spring House in Gorgeous Chadds Ford!
1010 out of 10 rating
Exceptional
(62 reviews)
Cozy Spring House in Gorgeous Chadds Ford!
Chadds Ford, PA
8% off
Price is AU$2,729
AU$2,729
AU$390 per night
includes taxes & fees
Image gallery for South Side Beauty. Newly renovated 4Br 2Bath, Central Air near downtown and Oaks
9.89.8 out of 10 rating
Exceptional
(13 reviews)
South Side Beauty. Newly renovated 4Br 2Bath, Central Air near downtown and Oaks
Phoenixville, PA
8% off
Price is AU$3,885
AU$3,885
AU$555 per night
includes taxes & fees
Image gallery for The Lodge at Cricklewood...where time melts away....
1010 out of 10 rating
Exceptional
(73 reviews)
The Lodge at Cricklewood...where time melts away....
West Chester, PA
8% off
Price is AU$16,536
AU$16,536
AU$2,362 per night
includes taxes & fees
Image gallery for Renovated 5 bedrooms. 6 beds. Great water pressure! New memory foam beds!
1010 out of 10 rating
Exceptional
(29 reviews)
Renovated 5 bedrooms. 6 beds. Great water pressure! New memory foam beds!
Downingtown, PA
8% off
Price is AU$3,385
AU$3,385
AU$484 per night
includes taxes & fees
Image gallery for Comfy, Cozy Woodlyn Home/Getaway Close to Sports, Highways, City + More!
9.89.8 out of 10 rating
Exceptional
(73 reviews)
Comfy, Cozy Woodlyn Home/Getaway Close to Sports, Highways, City + More!
Woodlyn, PA
8% off
Price is AU$3,023
AU$3,023
AU$432 per night
includes taxes & fees
Image gallery for Entire two-unit four-story townhouse, for multi-family vacations; free parking
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Entire two-unit four-story townhouse, for multi-family vacations; free parking
Wilmington, DE
12% off
Price is AU$6,539
AU$6,539
AU$934 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Underground Railroad Trail
HAWAII Indoors! Swim-up Tiki-Bar 20' Palms,5 waterfalls,2 Theaters,Pool, Spa,Gym
Sleeps 25 · 7 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
59 reviews(59 reviews)
Cheerful 3 bedroom home free parking on premise
Sleeps 8 · 3 bedrooms · 1 bathroom
8.48.4 out of 10
Very goodvery good
5 reviews(5 reviews)
Sleeps 6, 3BR 1BA,1King+2 Queen beds, perfect for long stays in a great location
Sleeps 6 · 3 bedrooms · 1 bathroom
7.07.0 out of 10
Goodgood
10 reviews(10 reviews)
Cozy 2-bedroom apartment with AC and WiFi in awesome Boothwyn
Sleeps 4 · 2 bedrooms · 1+ bathroom
9.29.2 out of 10
Wonderfulwonderful
11 reviews(11 reviews)
Private townhouse near downtown and state park
Sleeps 6 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Vacay in an Authentic Chadds Ford / Brandywine Valley / Longwood Gardens
Sleeps 19 · 6 bedrooms · 5+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
39 reviews(39 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