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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 Havertown

4.95 out of 5 average rating, 118 reviews

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!

Guesthouse in Media

4.95 out of 5 average rating, 482 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.

Guest suite in Wilmington

4.99 out of 5 average rating, 243 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.

Tiny home in Wilmington

4.97 out of 5 average rating, 321 reviews

Unbelievably Charming Tiny Home

Completely private stand alone tiny house, comfortable for 1-4 people. Guaranteed the absolute coziest place to stay in Trolley Square. Unusual amenities include: - *Homemade ice cream* - Loaded pantry and fridge - Yoga mats, blocks, & YogaGlo subscription - King size lofted bed Downtown Trolley and Brandywine Park are less than a minute walk. Right next to restaurants, Acme, several coffee shops, bus stop, and bars. Close to many attractions including Longwood Gardens and Winterthur.

Rental unit in Prospect Park

4.9 out of 5 average rating, 113 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.

Rental unit in Swarthmore

4.88 out of 5 average rating, 253 reviews

Skylight second floor apartment

Second 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.

Guest suite in Media

4.89 out of 5 average rating, 199 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, 469 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

4.92 out of 5 average rating, 119 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.

Guesthouse in Wilmington

4.85 out of 5 average rating, 395 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, 218 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!

Cottage in Coatesville

5 out of 5 average rating, 222 reviews

Charming cottage on 50 acre Chester County farm

Frog Hollow Cottage is a newly renovated getaway located in the heart of the Chester County’s rolling farmland and equestrian community. Overlooking beautiful pastures, the cottage was formerly the large painting studio of Delaware Valley artist Peter Sculthorpe. The studio has been re-imagined as a peaceful retreat for families, friends and couples.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

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

Subaru Park5 locals recommend

Harrah's Philadelphia8 locals recommend

Widener University3 locals recommend

2SP Brewing Company4 locals recommend

Wawa4 locals recommend

Portobello Cafe6 locals recommend

Other great vacation rentals in Chester

Cottage in North East

4.94 out of 5 average rating, 301 reviews

Cottage Just Off North East's Main Street

Loft in Roxborough

4.95 out of 5 average rating, 908 reviews

2020 All New modern STUDIO with brunch.

Guest suite in Paoli

4.97 out of 5 average rating, 216 reviews

A 650 SF Condo| Walking distance to Amtrak station

Farm stay in Elverson

4.96 out of 5 average rating, 220 reviews

Glasshouse overlooking the Great Marsh

Home in Manayunk

4.94 out of 5 average rating, 236 reviews

Shurs Lane Cottage, EV Charging, Free Parking

Rental unit in West Chester

4.9 out of 5 average rating, 116 reviews

Apartment in West Chester

Home in Sharon Hill

4.81 out of 5 average rating, 199 reviews

Cozy Haven 5 mins from airport/Parking/Patio

Rental unit in Kennett Square

4.92 out of 5 average rating, 212 reviews

Cozy, Creative, Fun Getaway Spot

Quick stats about vacation rentals in Chester

Total rentals
30 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
440 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 house rentals in Chester have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Chester. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Chester?
Experience the best of Chester with our house 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.

Destinations to explore