Holiday Homes in Chester Springs

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Chester Springs

Luxury Oasis with Resort-Style Pool, Spa & Outdoor Living — Just Outside Philly
Outdoor pool, a heated pool

Luxury Oasis with Resort-Style Pool, Spa & Outdoor Living — Just Outside Philly

10.0 out of 10, Exceptional, (3)
""Had a wonderful two-day stay at this lovely house! It was impeccably clean and had all the amenities we needed for our family. The location was perfect, . Our host was incredibly hospitable and made sure we had everything we needed. Overall, it was a comfortable and enjoyable experience, and we would definitely recommend this place to others!" "
Luxury Oasis with Resort-Style Pool, Spa & Outdoor Living — Just Outside Philly
Sleeps up to 18 people, perfect for a family getaway
Outdoor dining

Sleeps up to 18 people, perfect for a family getaway

9.8 out of 10, Exceptional, (14)
"Nice and clean!"
Sleeps up to 18 people, perfect for a family getaway
Charming 4 bedroom FarmHaus, circa 1790, renovated on Scenic Byway.
Property grounds

Charming 4 bedroom FarmHaus, circa 1790, renovated on Scenic Byway.

10.0 out of 10, Exceptional, (37)
"Beautiful place to stay. Wonderful amenities and beautiful area!"
Charming 4 bedroom FarmHaus, circa 1790, renovated on Scenic Byway.
Ushmila's Nest - Private suite with 2 rooms & Bathroom.
Exterior

Ushmila's Nest - Private suite with 2 rooms & Bathroom.

9.8 out of 10, Exceptional, (43)
"Beautiful property- close to restaurants and Main Line spots. "
The price is NZ$320
includes taxes & fees
1 Sept - 2 Sept
Ushmila's Nest - Private suite with 2 rooms & Bathroom.
Lovely Private Guesthouse with AC & WiFi in Shillington
Exterior

Lovely Private Guesthouse with AC & WiFi in Shillington

8.8 out of 10, Excellent, (8)
"Property was perfect for my stay, hope to book again."
The price is NZ$263
includes taxes & fees
2 Sept - 3 Sept
Lovely Private Guesthouse with AC & WiFi in Shillington
Expansive Modern Farm House On 8 Park-Like Acres
Outdoor pool, a heated pool

Expansive Modern Farm House On 8 Park-Like Acres

10.0 out of 10, Exceptional, (82)
"This is a wonderfull house to host a large mixed family group. There is so much common space on the main floor and the house is well appointed. We came with a multi-generational family group and the house made it very easy for everyone to enjoy the visit. "
Expansive Modern Farm House On 8 Park-Like Acres
Newly remodeled Spacious 4-BM house in Phoenixville with OS parking/ central, AC
Exterior

Newly remodeled Spacious 4-BM house in Phoenixville with OS parking/ central, AC

10.0 out of 10, Exceptional, (3)
"Everything was as advertised. Communication with property owner was easy, and received prompt replies."
Newly remodeled Spacious 4-BM house in Phoenixville with OS parking/ central, AC
Vacay in an Authentic Chadds Ford / Brandywine Valley / Longwood Gardens
Interior

Vacay in an Authentic Chadds Ford / Brandywine Valley / Longwood Gardens

9.8 out of 10, Exceptional, (39)
"We had a great stay at this house while in town to celebrate our aunt's 90th birthday. The property was big enough to accommodate our 16 family members and we loved the historic charm. The busy road was a bit noisy but overall we had a wonderful time - thank you Vicki for a great experience!"
The price is NZ$2,920
includes taxes & fees
22 Sept - 23 Sept
Vacay in an Authentic Chadds Ford / Brandywine Valley / Longwood Gardens
The Lodge at Cricklewood...where time melts away....
Dining

The Lodge at Cricklewood...where time melts away....

10.0 out of 10, Exceptional, (73)
"My family and I throughly enjoyed our short stay at Eric’s property. It a beautiful home in beautiful landscapes. The home is fully stocked and made our celebration of a graduation weekend memorable and successful. "
The Lodge at Cricklewood...where time melts away....
Homestead Guesthouse
Property grounds

Homestead Guesthouse

10.0 out of 10, Exceptional, (21)
"I enjoyed remarkable place, the place where you need to go with your family. We have all the access."
The price is NZ$493
includes taxes & fees
25 Aug - 26 Aug
Homestead Guesthouse
Homey Retreat in Historic Kennett Square!!
Fridge, microwave, oven, stovetop

Homey Retreat in Historic Kennett Square!!

10.0 out of 10, Exceptional, (80)
"So convenient and easy to walk to shops and food! The house is adorable and clean. Looking forward to staying again. "
The price is NZ$560
includes taxes & fees
2 Sept - 3 Sept
Homey Retreat in Historic Kennett Square!!
Cozy Farmhouse in Greenville, DE
Fridge, microwave, oven, stovetop

Cozy Farmhouse in Greenville, DE

10.0 out of 10, Exceptional, (24)
"Super clean house that’s perfect for a group gathering "
Cozy Farmhouse in Greenville, DE
Historic Farmhouse in Chester County
Terrace/patio

Historic Farmhouse in Chester County

10.0 out of 10, Exceptional, (7)
"This property was historic but maintained so well it felt very comfortable!"
The price is NZ$464
includes taxes & fees
2 Sept - 3 Sept
Historic Farmhouse in Chester County
Spacious home in Lancaster County PA with awesome backyard
Outdoor dining

Spacious home in Lancaster County PA with awesome backyard

9.8 out of 10, Exceptional, (47)
"This house is amazing, tons of space and was very enjoyable for my family to have a nice little get away"
Spacious home in Lancaster County PA with awesome backyard
Chester County Oasis with Pool, Modern Ammenities, Tranquil and Private
Exterior

Chester County Oasis with Pool, Modern Ammenities, Tranquil and Private

10.0 out of 10, Exceptional, (7)
"House is just as described. Spent a month here visiting family and friends. Will definitely book again! "
Chester County Oasis with Pool, Modern Ammenities, Tranquil and Private
K9 Cottage @ Berwyn MainLine
Fridge, microwave, oven, stovetop

K9 Cottage @ Berwyn MainLine

9.8 out of 10, Exceptional, (14)
"It was a great stay. My dog loves the backyard and the neighborhood is great for walking."
K9 Cottage @ Berwyn MainLine
Heritage Haven - West Chester Borough
Fridge, microwave, oven, stovetop

Heritage Haven - West Chester Borough

9.6 out of 10, Exceptional, (4)
"Great place and Michael could not have been more hospitable. "
The price is NZ$781
includes taxes & fees
24 Aug - 25 Aug
Heritage Haven - West Chester Borough
Ushmila's Nest- private entrance, bedroom & bathroom
Property grounds

Ushmila's Nest- private entrance, bedroom & bathroom

10.0 out of 10, Exceptional, (35)
"One night, everything that travelers could possibly need. Accommodations well done! "
The price is NZ$353
includes taxes & fees
24 Aug - 25 Aug
Ushmila's Nest- private entrance, bedroom & bathroom
The Rustic Old Farmhouse Peaceful home in Amish country,10 min from tourist area
Terrace/patio

The Rustic Old Farmhouse Peaceful home in Amish country,10 min from tourist area

10.0 out of 10, Exceptional, (69)
"We enjoyed our stay here. The farmhouse had plenty of room for us all and it was in a great location for visiting all the local attractions. The house was very clean and the kids loved the animals! "
The Rustic Old Farmhouse Peaceful home in Amish country,10 min from tourist area
Historic Village Retreat Convienient To Everything
Fridge, microwave, oven, stovetop

Historic Village Retreat Convienient To Everything

9.8 out of 10, Exceptional, (61)
"The house is beautiful and so is the town. The architecture and landscapes were really charming. Seemed to be a bit of french influence in the town. "
Historic Village Retreat Convienient To Everything
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Springs Hotel Reviews

Fairfield Inn by Marriott Kennett Square Brandywine Valley

Fairfield Inn by Marriott Kennett Square Brandywine Valley

10/10 Excellent
"very Quiet and comfortable."
Charles 2-night trip
Posted 12 hours ago
Fairfield Inn by Marriott Kennett Square Brandywine Valley