
Holiday rentals in Chester
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Top-rated holiday rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness and more.

By PHL airport - A++Clean, Disinfected, Sanitized.
A 1 bedroom & 1 bath fully furnished apartment in a quiet suburban neighborhood, 10 minutes from the PHL airport - Free Parking - Super clean, disinfected and sanitized after each guest check-out. - High-Speed Wi-Fi with Netflix, Amazon & Hulu-Live. - Eat-in kitchen with electric stove & regular and K-cup coffee. - Washer and Dryer facility located in the Gym/Laundry room (Gym currently closed). I can add a guest Gym membership to local Gym (30 days or more). - Available for long-term stays.

Claremont Cottage
Our one-bedroom suite is the perfect cozy getaway, whether you’re visiting Philadelphia or spending time in the surrounding area. We’re conveniently located near Media, Ardmore, Bryn Mawr, and many local colleges. While you’re here, cozy up to the electric fireplace, or enjoy time in the backyard or local neighborhood. We look forward to having you! Please note: Your "home away from home" is connected to our "home all the time," so please read the full space description before booking. Thanks!

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.

Refined Lavender Farm Escape with a Luxurious Spa
Escape to Windy Hill Lavender Farm, a luxurious countryside retreat surrounded by rolling hills and fragrant lavender blooms. Unwind in a spa-style bathroom with a tiled walk-in shower and deep soaking tub, then relax in the cozy queen bedroom or loft with 2 twin beds . Savor starry nights in the hot tub on the spacious deck, grill in the charming corncrib area, and gather by the fire pit. Perfect for romantic getaways, peaceful escapes, and unforgettable memories in nature’s beauty.

Charming historical home near Philadelphia
This 3 story victorian home sits on a treelined street nestled between a Quaker school and picturesque stone church. The 3rd floor apartment is resident occupied and the 1st and 2nd floors consist of 2+ bedrooms, kitchen, dining room and LR solely for AirBNB guests. Cozy up with a good book, cook a meal in the well appointed kitchen, relax by the outdoor fire pit and find your zen in the garden. Wifi and 2 parking spaces. Welcome to the Honeysuckle Hideout.

The Millhaus
This is the original "tiny house." Built in 1766, the Millhaus sits on a 32-acre historic site with the Knauer Mill, Horseshoe Trail, and French Creek. Take a short hike along the water's edge to Saint Peter’s Village for coffee & pastries, or dinner & drinks. Recharge with modern touches like onsite massage and private fitness amenities, available by appointment. Stay put and unwind—or venture out and explore the best of PA from this beautiful location!

The Farmer’s House
Historic FARM STAY. Est. In 1757 and hidden from view, it is certain to provide a private getaway! If you have the heart of a "homesteader" or simply want to have a peaceful holiday, this farmette will allow you to travel back in time for a relaxing experience you will not forget! A winding brook and pond are located within short walking distance from the home. Well furnished, this home will impress you with all her comfort and character!

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

Tranquil Hilltop Retreat
Escape to a peaceful retreat in our newly remodeled two-bedroom guest cottage, situated atop a scenic hill in Glen Mills. With its light-filled interior and modern amenities, this 1,100 sq ft cottage provides the perfect respite from the hustle and bustle of nearby Media and West Chester. Wake up to the tranquil sounds of nature and enjoy your morning coffee on the cobblestone patio, where you can watch the deer graze in the yard.

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

Downtown Luxe Retreat + Free Garage Parking

Single level home, private yard, kid/pet friendly

Work-Ready Retreat with King Bed

Radiant 4-Bed Haven w/ King suite in N. Wilmington

Vintage Waterfront Cottage with Stunning Sunsets

Jacuzzi/Game Room/Close to Airport/Philly Stadiums

Convenient 1 BR 24 minutes from FIFA World Cup

Stylish 3-Bdrm Home Near Airport, Stadiums & City
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 51 | € 55 | € 47 | € 51 | € 51 | € 53 | € 60 | € 60 | € 60 | € 60 | € 60 | € 60 |
| 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 130 vacation rentals in Brookhaven, over 130 vacation rentals in Upland, and over 350 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 50 holiday rentals in Chester

Nightly prices starting at
Chester holiday rentals start at € 17 per night before taxes and fees

Verified guest reviews
Over 680 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
40 of Chester holiday rentals include wifi access

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

4.5 Average rating
Chester stays receive an average rating of 4.5 out of 5 from guests
Destinations to explore
- Norfolk Holiday rentals
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pennsylvania Convention Center
- Lincoln Financial Field
- Sesame Place
- Longwood Gardens
- Citizens Bank Park
- Fairmount Park
- Wells Fargo Center
- Philadelphia Museum of Art
- Penn's Landing
- Bear Creek Ski and Recreation Area
- Temple University
- Diggerland
- University of Pennsylvania
- Dutch Wonderland
- Philadelphia Zoo
- 30th Street Station
- The Franklin Institute
- French Creek State Park
- Marsh Creek State Park
- Valley Forge National Historical Park
- Wissahickon Valley Park
- Independence Hall
- Franklin Square
- Aronimink Golf Club





