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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Top guest favourite
Barn in Wayne
5 out of 5 average rating, 100 reviews

World Cup Star Carriage House:PhillyVillanovaWayne

Escape to this tucked away apartment in a Main Line carriage house. Located 5 min from Villanova University & downtown Wayne; 10 min from King of Prussia; short walk to Radnor Train Station gets you to Philadelphia in 30 min with access to NYC and D.C. With a private entrance, full kitchen, bath, and bedroom, we preserved the cedar shake exterior, wood beams & floors, & exposed the cupola. Perfect for university visits, Valley Forge National Park, or Philly access without staying in the city.

Top guest favourite
A bright sunroom is filled with natural light from large windows, offering views of greenery. It features comfortable seating with colorful cushions, a patterned area rug, and decorative artwork on the wall. A small lamp and a side table complete the inviting space.
Apartment in Swarthmore
4.89 out of 5 average rating, 322 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.

Guest favourite
A bright living room is displayed, featuring a blue sectional sofa and a glass coffee table atop an area rug. Natural light enters through a large window, framed by light-colored curtains. A ceiling fan is positioned above, and a black armchair is located in the corner.
Apartment in Prospect Park
4.91 out of 5 average rating, 222 reviews

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.

Top guest favourite
A sunlit sunroom features large windows surrounded by vibrant greenery. A well-maintained lawn is visible with flowering shrubs in shades of pink, complemented by a wheelbarrow nearby. The brick exterior of the home provides a classic touch to the inviting outdoor space.
Apartment in Wilmington
4.83 out of 5 average rating, 425 reviews

“McDaniels Corner” (Cozy Home in North Wilmington)

When you step into "McDaniel's Corner" you get a Quiet and Modern Feel in a 'Cozy' Early Twentieth Century brick home. This cozy home has our guests feeling comfortable and relaxed while providing modern day luxuries in this historic home. You can’t beat this central location close to Longwood gardens, Winterthur, the Nemours Estate and so much more. There are also tons of great restaurants, bars, supermarkets, coffee shops, Nemours Children’s Hospital and so much more to see and do.

Top guest favourite
A bright and airy living area features a brown leather couch and a wooden coffee table on a patterned rug. Natural light filters through sheer curtains by a cozy reading chair. The open-plan space includes a kitchen visible in the background, highlighted by modern fixtures.
Cottage in Downingtown
4.97 out of 5 average rating, 351 reviews

The Cottage at Marsh Creek (with hot tub!)

Peaceful, renovated cottage with year-round hot tub less than a mile from Marsh Creek State Park and lake! 1 bedroom (with king size bed!), 1 bathroom The park has hiking, fishing & water sports. Close to great dining, breweries, coffee, & other activities, but far enough from town to feel relaxing & somewhat secluded. Dog friendly! You'll have access to the entire home, including the private patio with string lights & hot tub. Follow us on IG! @thecottageatmarshcreek

Top guest favourite
The bedroom features a spacious bed with neutral-colored linens and a decorative pillow. A side table and a chair are present, with a lamp providing soft lighting. A piece of artwork hangs above the bed, and a window allows natural light to filter in.
Apartment in New Castle
4.97 out of 5 average rating, 141 reviews

King Bed - Center of Historic District

This cute 1 bedroom apartment is located at the HEART of our lovely town. Steps away from some of the most historic places in the entire United States. Come near the weekend and you can tour our informative museums and wayside exhibits while taking in the local culture. We are a close-knit town and are happy to show out-of-towners "the way". On days we are open enjoy a $15/day credit to our cafe next door. Please enjoy your stay! We are so sorry but no pets allowed.

Top guest favourite
A bright bedroom features a cozy Queen bed layered with soft blankets. A light-colored armchair sits beside a small table. A wall-mounted television is positioned across from the bed, and large windows allow natural light to fill the space, framed by soft curtains.
Condo in Northern Liberties
4.99 out of 5 average rating, 110 reviews

New NoLibs Cozy Studio

Location! Located in Northern Liberties and a few blocks from Fishtown, the restaurant options are endless. Walk down North 2nd Street or over to Frankford Ave for just about any cuisine you can think of. 5 Minute drive to Old City and 10 minute drive to Center City. Walk to your show at the Fillmore or a quick drive to The Met. Enjoy a spacious new construction studio with a cozy Queen Bed, full Kitchen, full Bath, Laundry Closet and private Balcony!

Top guest favourite
A charming cottage with a green, A-frame roof is framed by blossoming dogwood trees. A gravel path leads to the entrance, which is flanked by lush greenery and flowering shrubs, providing a tranquil and inviting approach.
Place to stay in West Chester
4.99 out of 5 average rating, 268 reviews

Private West Chester Cottage close to Longwood

Treat yourself to time away in the heart of Chester County history and horse country. This charming little gem, privately nestled under the evergreens is surrounded by acres of American history dating back to the 1700s. Tucked behind the property's historic stone farmhouse is the newly refurbished cottage which you'll have to yourself. The cottage is tastefully decorated with vintage treasures & has spectacular views of the unique property & gardens.

Top guest favourite
The living room is furnished with two patterned armchairs and a floral couch, creating a comfortable seating area. A ceiling fan is visible above, and natural light enters through a window. An open layout leads to the kitchen, featuring white cabinetry and modern appliances.
Home in Wilmington
4.97 out of 5 average rating, 115 reviews

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

Guest favourite
The cottage exterior features a blend of natural stone and siding, showcasing a green front door. Lush green grass surrounds the home, complemented by trees in the backdrop. A gravel path leads to the entrance, providing access to the peaceful surroundings.
Cottage in Glen Mills
4.91 out of 5 average rating, 118 reviews

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.

Superhost
A bright kitchen area features a wooden dining table surrounded by four metal chairs. Against the wall, a white stove and a black microwave are positioned, with a window allowing natural light. A few decorative elements and wall art enhance the space.
Apartment in Media
4.77 out of 5 average rating, 329 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!

Top guest favourite
A forest path is surrounded by tall trees and dense greenery, with ferns lining the ground. The sunlight filters through the leaves, creating a serene atmosphere for hikers. The trail, partially obscured by foliage, invites exploration into the natural surroundings.
Guest suite in Media
4.98 out of 5 average rating, 592 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. The woods are waiting to welcome you!

Popular amenities for Chester vacation rentals

When is the best time to visit Chester?

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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 vacation rentals in Chester

  • Total vacation rentals

    Explore 50 vacation rentals in Chester

  • Nightly prices starting at

    Chester vacation rentals start at $28 CAD per night before taxes and fees

  • Verified guest reviews

    Over 680 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of Chester vacation 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

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