
Holiday houses in Chester
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Top-rated holiday rentals in Chester
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Swarthmore Guesthouse
Welcome to this stylish and comfortable 1BR, 1.5BA home in Swarthmore! Just a few blocks from the College, The Ville, and train, this recently remodeled guesthouse sleeps 2 and blends charm with modern flair. Once a bike shop, it now boasts an open concept layout with exposed beams, full kitchen, 2 TVs, washer/dryer, private entrance & parking, and AC/heat with ceiling fans. Perfect for short or long stays in a prime location. Enjoy the whole house to yourself! No smoking, no parties, no pets.
Treetop Studio at Ridley Creek State Park
Enjoy the view of the treetops outside this secluded and bright studio while listening to limitless free music on the smart speaker. Unique touches include exposed beams, sliding barn door and European-style bathroom with large tiled shower. Enjoy original artwork hanging on the walls, a nod to Philadelphia's thriving art scene. Designed and decorated using a combination of American & European influences, the high quality finishes and accessories make this 280 square foot space feel like home.

Skylight second floor apartment
Second, 3rd floor apartment. Apartment includes a master bedroom with a full sized bed and a guest bedroom with 2 twin beds. Private bathroom. There is a dining area with refrigerator, sink,microwave,induction hot pate convection toaster oven, coffee maker, french press dining table,Alexa and LCD TV. The dining area does NOT have a STOVE. 3rd floor meditation room with skylights and sitting area with LCD. ALL APARTMENT AREA IS PRIVATE. Home backs up to woods and back garden. NO CLEANING FEES.

2BR Cozy Apt 1 mi from Airport (PHL) Free Parking
Newly Renovated, centrally located Multi-unit home in a suburban neighborhood. This 1st Floor unit is a 2BR/1BA apartment with a private entrance. Complete with all you need for a work trip, get away or longer stay. The unit features a full kitchen, living room with pull out couch. The Kitchen has full sized stainless steel appliances, dishes, cookware and small kitchen appliances. There is fast Wi-fi, Keyless entry/self check-in, Smart TV's in each room and an in unit Washer and Dryer.

Lovely 1-bedroom unit with parking on premises
Kick back and relax in this calm, very private, stylish space, in a safe and quiet neighborhood. The apartment is in mint condition and recently renovated. We are within walking distance (9 blocks) to the Media/Elwin SEPTA Regional Rail, which takes you to Center City Philadelphia. We are also only a one-mile walk to the beautiful Swarthmore College Campus. We are 2.5 miles from I-476, I-95, supermarkets, restaurants, and the Springfield Mall. The PHL airport is 15 minutes away.

CoZy Super Clean, Sanitized, Disinfected-PEACEFUL.
Beautiful, cozy, sunny room with a super comfy L-shaped sectional sofa. Super clean and spacious fully equipped Eat-in kitchen with dishwasher, stove, oven, microwave, regular and K-Cup coffee makers, Micro-wave, Toaster, Pots, Pans, Utensils, and Silverware all provided. The apartment includes (2) 43" Flat Screen TVs; streaming HULU-Live, Amazon Prime, Disney Plus. Also, a little work desk area provided Free washer/dryer access and Free parking, (short-term lease available).

Modern and Relaxing downtown Apartment
Enjoy a relaxing experience in this modern & centrally-located apartment! This wonderful apartment is on the 2nd floor of an exquisite private building. With 1Bedroom/1Full Bathroom and 2Beds, this unit comfortably sleeps 4! Free street parking around the property. Located in University City you're close to U Penn/Drexel/CHOP. It's a great property for family getaways, reunions, and traveling business partners looking to enjoy what the City of Brotherly Love has to offer.

Funky Private Attic Apartment in Honey Brook
A private one bedroom attic apartment - perfect for a weekend getaway or solo time 🫶🏼 *please be aware that this property is alongside a main road, so if traffic noise bothers you, this may not be the right fit Located in the Borough of Honey Brook & just a mile from September Farm Cheese Shop & wonderful thrift stores! Pickleball courts within walking distance in local park. Paddles and balls provided. Lancaster County Tourist towns - within 25 min.

The Lighthouse
Centrally located in northern Delaware with easy on/off access to 95 and 495. Newer construction, built in 2018. One large bedroom with KING size bed, 1.5 bath, private entrance, living room and full eat in kitchen. Work station area. Twin size pull out in living room. Free WiFi and large smart TVs in living room and bedroom. Deck off of the kitchen and upstairs deck off of the bedroom. Laundry located in bedroom upstairs. NO CLEANING FEE

Town & Country III: Private Apt, Minutes from City
Get the best of both town and country during your next trip to Philadelphia. Stay in a well-appointed, modern private apartment in the carriage house of a beautiful brick colonial revival home (built 1890) in quiet Lansdowne, PA - minutes from the airport and downtown Philly. A short walk to regional rail (5 stops to Center City), Lansdowne's popular farmer's market, and local restaurants. Oh and free off-street parking (one spot)!

Media's Hidden Gem!
Welcome to Media's Hidden Gem! Nestled on a quiet block in everybody's hometown Media. Just a couple blocks from all that downtown has to offer. Enjoy some time away on the nice deck, and check out the completely renovated bathroom. You won't be dissapointed with this one. Perfect set up for the weekend away or the business traveler. We went above and beyond to make sure this is a space you can call home!

The Welcoming Woods
Enjoy the quiet of the woods as you relax in your private space. The studio is minutes away from downtown Media where you can enjoy the shops & restaurants on State St or take a 20 minute ride into Philadelphia. Attractions include Tyler Arboretum, Ridley Creek State Park,Longwood Gardens,Linvilla Orchards & local wineries in Brandywine & Chadds Ford PA. The woods are waiting to welcome you!
Popular amenities for Chester holiday rentals
Other great holiday rentals in Chester

Cottage Mini Suite

Private Studio w/deck, near train to center city.

The Rococo Room

Private Room & Bath (Perfect for Meds & Eds)

King of Prussia 10mins, Valley Forge Park 5mins!

Comfy room in a convenient location in N. Wilm

Lovely, Serene Hilltop Home

Room in 3BR Twin House
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $84 AUD | $90 AUD | $77 AUD | $84 AUD | $84 AUD | $87 AUD | $98 AUD | $98 AUD | $98 AUD | $98 AUD | $98 AUD | $98 AUD |
| Avg. temp | 1°C | 2°C | 6°C | 13°C | 18°C | 23°C | 26°C | 25°C | 21°C | 15°C | 9°C | 4°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Chester?
Chester has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in apartment rentals in Chester?
Experience the best of Chester with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Chester?
Yes! Work meets play with ease at over 30 vacation rentals in Chester featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Chester?
Make yourself at home in Chester by choosing from our most frequently booked neighborhoods. We have over 120 vacation rentals in Brookhaven, over 120 vacation rentals in Upland, and over 330 vacation rentals in Woodlyn.
Do apartment rentals in Chester have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Chester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chester have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Chester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chester have wifi?
Absolutely! We offer over 20 house rentals with wifi in Chester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chester have free parking?
Absolutely! We offer over 20 house rentals with free parking in Chester. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Chester

Total holiday rentals
Explore 40 holiday rentals in Chester

Nightly prices starting at
Chester holiday rentals start at $28 AUD per night before taxes and fees

Verified guest reviews
Over 610 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
40 of Chester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chester rentals

4.6 Average rating
Chester stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
- Plainview Holiday rentals
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- Philadelphia Holiday rentals
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- Pennsylvania Convention Center
- Lincoln Financial Field
- Sesame Place
- Longwood Gardens
- Citizens Bank Park
- Fairmount Park
- Philadelphia Museum of Art
- Wells Fargo Center
- Penn's Landing
- Bear Creek Ski and Recreation Area
- Diggerland
- French Creek State Park
- Philadelphia Zoo
- The Franklin Institute
- Wissahickon Valley Park
- Marsh Creek State Park
- Valley Forge National Historical Park
- Independence Hall
- Spruce Street Harbor Park
- Eastern State Penitentiary
- Franklin Square
- Ridley Creek State Park
- Clark Park
- Philadelphia's Magic Gardens




