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Vacation rentals in Chester

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Top-rated vacation rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest suite in Wilmington

4.99 out of 5 average rating, 254 reviews

Private Guest Suite and Entrance

Seeking a romantic getaway or respite from a long work day? You'll love relaxing "at home" in your private 1 BR suite. We are located in a tree lined quiet community. Convenient shopping & restaurants are within walking distance. Short & extended rentals for business travelers or those relocating. Minutes from historic Chadds Ford & the scenic Brandywine Valley, plan to tour our Wine & Ale Trail, hike our greenways or experience the many duPont Chateau's with their glorious gardens & grounds.

Guesthouse in Media

4.96 out of 5 average rating, 500 reviews

Studio Apartment in Attractive Sylvan Setting

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.

Rental unit in Swarthmore

4.88 out of 5 average rating, 263 reviews

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.

Rental unit in Prospect Park

4.92 out of 5 average rating, 140 reviews

2BR Cozy Apt 1 mi from Airport (PHL) Free Parking

Newly Renovated, centrally located Multi-unit home in a quiet 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.

Guest suite in Media

4.89 out of 5 average rating, 216 reviews

Spacious Suite in Spectacular Neighborhood

You will have the first floor of a private residence. All entrances, rooms, doors are untouched except by guests for entire stay. There is a locking french doors between the suite and the rest of the home. The living room has a fire place. TV and a high top seating area. The suite includes a fully functional kitchen -- sink, fridge, dishes, microwave etc. there is a hot plate (2) but not a range top stove. There is patio with secluded and private seating. and gas grill.

Guest suite in Media

4.98 out of 5 average rating, 491 reviews

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. After a day of activities relax on the hammock or enjoy a soak in the hot tub. The woods are waiting to welcome you!

Rental unit in Media

4.91 out of 5 average rating, 127 reviews

Pennell Apartment- By Neumann Univ

Welcome to the apartment on Pennell! This apartment offers a modern, recently renovated peaceful and private setting right next to the woods! Large windows allow natural light to spill into the open-concept living space. Expect to see deer and other wildlife. Our place is 2 minutes from Barnaby' restaurant, 5 minutes from Linvilla Orchards & Neumann University & also 15 minutes from State Street in Media where you can enjoy food, drinks, shopping and or just strolling.

Serviced apartment in Chadds Ford

4.99 out of 5 average rating, 123 reviews

Silo Suite

Welcome to our charming suite located in the heart of the historic Brandywine Valley. Nestled within the entrance of a beautifully converted 12,000 square foot barn home, this space offers a truly unique and memorable stay. Our special place is perfectly situated between the renowned Brandywine River Museum and the Chadds Ford Winery, and in just minutes, you can explore the enchanting beauty of Longwood Gardens or dive into the world of history at Winterthur.

Guesthouse in Wilmington

4.85 out of 5 average rating, 420 reviews

Beautiful Modern Fully Equipped Private Guesthouse

Beautiful and modern brand new private apartment. This space is brand new and fully sanitized at all moments. Completely separate space with private entrance, patio, bathroom and kitchenette. Enjoy Netflix on our extra large living room tv or a glass of wine from our honor bar! Location is excellent in a beautiful safe neighborhood with convenient access to I-95, downtown Wilmington and shopping centers.

Rental unit in Media

4.78 out of 5 average rating, 235 reviews

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!

Loft in Roxborough

4.95 out of 5 average rating, 937 reviews

All New Modern Studio with brunch

Check out our modern, updated studio located in Roxborough, near the historic Manayunk neighborhood of Philadelphia—perfect for couples and business travelers. You'll have the entire space to yourself, and we’ll provide a parking permit for public lots. Additionally, enjoy a $20 gift certificate to Taylor Café for each night of your stay. Please note that the café is closed on Tuesdays and Wednesdays.

Guest suite in Wilmington

4.89 out of 5 average rating, 267 reviews

InLawSuite

Cozy In Law Suite apt in quiet neighborhood 20 minute drive from PHL airport. Fully equipped kitchen. Cable TV. WiFi access. Non-Smoking. We have a screened in porch that you are welcome to enjoy but it's a community gathering. If you enjoy games we have card games, board games and domino. Happy to direct to any local attractions or new events in the area.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

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Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Chester vacation rentals

Free parking on premises

Air conditioning

Stay near Chester's top sights

Linvilla Orchards15 locals recommend

Harrah's Philadelphia8 locals recommend

Portobello Cafe6 locals recommend

Subaru Park5 locals recommend

Wawa4 locals recommend

2SP Brewing Company4 locals recommend

Other great vacation rentals in Chester

Rental unit in Wilmington

4.96 out of 5 average rating, 27 reviews

Luxury Condo + Free Garage parking 201

Rental unit in Wallingford

4.97 out of 5 average rating, 35 reviews

Private Suite

Home in Wilmington

4.95 out of 5 average rating, 43 reviews

The Lighthouse

Rental unit in Swarthmore

4.91 out of 5 average rating, 35 reviews

Sweet Solace

Rental unit in Morton

5 out of 5 average rating, 88 reviews

Lovely 1-bedroom unit with parking on premises

Guest suite in Nether Providence Township

4.87 out of 5 average rating, 76 reviews

Private Room near Swarthmore & PHL Airport

Rental unit in Folcroft

5 out of 5 average rating, 12 reviews

Creekside Lower Level Apartment near PHL

Rental unit in Media

4.92 out of 5 average rating, 86 reviews

Lemon St. Retreat

Quick stats about vacation rentals in Chester

Total rentals
30 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
240 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

Frequently Asked Questions

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.
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 20 vacation rentals in Chester featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Chester have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Chester. Enjoy a tailored experience with all the comforts you desire.
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.
Do house rentals in Chester have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Chester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chester have free parking?
Absolutely! We offer over 10 house rentals with free parking in Chester. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Chester?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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