Holiday Homes in Chester

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Featured Holiday Homes in Chester

Our top choices for Chester holiday homes

Stylish, Modern 2-Bedroom Retreat, Central with WiFi & AC

8.6 out of 10, Excellent, (8)
"This was a good base for exploring the Fishtown area, and going to a show at Johnny Brenda's."
The price is AU$288
includes taxes & fees
29 Aug - 30 Aug
Stylish, Modern 2-Bedroom Retreat, Central with WiFi & AC

Private room, attached pvt bath. Couple's retreat in U. City. Penn. Free Park.

7.4 out of 10, Good, (21)
"Very clear check in and check out instructions. Amenities were as listed, the room and bathroom were very clean and tidy, and it was a perfect distance from downtown. I was very pleased with my stay. "
The price is AU$307
includes taxes & fees
23 Aug - 24 Aug
Private room, attached pvt bath. Couple's retreat in U. City. Penn. Free Park.

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 AU$295
includes taxes & fees
24 Aug - 25 Aug
Ushmila's Nest - Private suite with 2 rooms & Bathroom.

Stylish Home 4BD/4BATH/2 Indoor Car Garage near all Stadiums and Center City

9.4 out of 10, Exceptional, (40)
"The place was very clean and checked all the boxes. We all had a great time. Rooftop view was amazing!"
The price is AU$643
includes taxes & fees
15 Sept - 16 Sept
Stylish Home 4BD/4BATH/2 Indoor Car Garage near all Stadiums and Center City

Historic house Ideal Downtown Location

9.2 out of 10, Wonderful, (49)
"Our stay was brief but we feel rested. We love the giant mirror in the living room and the furnace kept us warm. Also, the street was amazingly quiet for being so close to South Street.We'll definitely be back!"
The price is AU$406
includes taxes & fees
24 Aug - 25 Aug
Historic house Ideal Downtown Location

Heart Of South Philly

9.6 out of 10, Exceptional, (25)
"It was a great stay "
Heart Of South Philly

The Executive South Philadelphia/4BR/3Bath/King-Bed/Roof-Deck/Luxury

10.0 out of 10, Exceptional, (2)
"We had a one night stay with another family, 4 adults and 3 kids. The space was big and clean. We had a great stay. Would recommend!!"
The price is AU$1,084
includes taxes & fees
16 Sept - 17 Sept
The Executive South Philadelphia/4BR/3Bath/King-Bed/Roof-Deck/Luxury

Stylish 3 Bed Near Center City I Exposed Brick+Art

4.0 star property
9.6 out of 10, Exceptional, (21)
"I had a really pleasant stay here for my brother's graduation from college in the area. Parking was a hit or miss since it is street parking, but for 2 nights, it wasn't bad. The space sleeps 4 comfortably. It was clean, and the property host was very communicative and accommodating!"
Stylish 3 Bed Near Center City I Exposed Brick+Art

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 AU$2,674
includes taxes & fees
24 Aug - 25 Aug
Vacay in an Authentic Chadds Ford / Brandywine Valley / Longwood Gardens

Exquisitely Designed Gem! Roof Deck+Patio

10.0 out of 10, Exceptional, (1)
"Our group of 12 all stayed comfortably. Everyone loved the pproperty. Nothing was missing. Location was great, close to lots of great restaurants. Parking is a nightmare but that’s city life and nothing to do with the property itself. That being said, the neighbors were friendly with one even helping us find a parking spot right nearby. The owners also recommended a parking lot about a mile away. Communication was great, and we had no issues whatsoever. This will be the first place we look up...
Exquisitely Designed Gem! Roof Deck+Patio

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....

Huge MODERN LUXE Home | Minutes to Center City!

4.0 star property
9.6 out of 10, Exceptional, (33)
"The house was in a great location and had lots of space"
Huge MODERN LUXE Home | Minutes to Center City!

Philly's Perfect Pad: Park Views, Parking & Walkable Charm!

9.8 out of 10, Exceptional, (20)
"We stayed for a girls weekend to experience Philly. Everything' we wanted to do or see was right around the corner. Definately would stay again."
Philly's Perfect Pad: Park Views, Parking & Walkable Charm!

A Regal Retreat- Exclusive Parking Prime Local

9.6 out of 10, Exceptional, (9)
"Visited Philly for the flower show with friends. The property is spacious, beautiful, and has great amenities. Easily walkable to Old City and all the benefits of Society Hill. Host is very responsive!"
A Regal Retreat- Exclusive Parking Prime Local

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 AU$515
includes taxes & fees
4 Sept - 5 Sept
Homey Retreat in Historic Kennett Square!!

Walk to South Philly's Best Restaurants & Bars!

9.6 out of 10, Exceptional, (8)
"We had a great time. The location was amazing walking distance to so many restaurants the Italian market and the Magic Gardens would recommend and would stay again."
Walk to South Philly's Best Restaurants & Bars!

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

Live & Work in Style

10.0 out of 10, Exceptional, (8)
"This is a charming 4 level home in a quiet courtyard within walking distance to many historic sites, shops, bars and restaurants. Beautifully renovated inside, quiet, super clean, comfortable bed. We lucked out with street parking on arrival. We used the narrow lane in the rear to quickly load our car when leaving. Overnight parking at the 10th and South Street lot was convenient. We much preferred staying here vs center city hotel. "
Live & Work in Style

Fantastic 4BR Townhouse W/ HOTTUB

2.0 star property
The price is AU$423
includes taxes & fees
4 Sept - 5 Sept
Fantastic 4BR Townhouse W/ HOTTUB

Spacious Home with Antique Decor

10.0 out of 10, Exceptional, (23)
"Absolutely beautiful home in a perfect location. We really enjoyed our stay. "
Spacious Home with Antique Decor
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.
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Top Chester Hotel Reviews