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Vacation rentals in Chester

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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 G$4,182 GYD per night before taxes and fees

  • Verified guest reviews

    Over 710 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Chester vacation 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

Top-rated vacation rentals in Chester

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

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Guest favorite
Home in Nether Providence Township
4.96 out of 5 average rating, 24 reviews

Tranquil Haven: Stylish Home Surrounded by Nature

Welcome to your suburban retreat, 15 minutes from Philadelphia International Airport and 10 minutes from Swarthmore College. This 650 sq ft home features a comfortable living area, one bedroom, and a well-equipped kitchen. Enjoy outdoor space in the front and backyard. Located in the Wallingford-Swarthmore school district, you'll also be minutes away from charming Media, with its shops and dining. 20 minutes from Philadelphia sports center (including Lincoln Financial Field), open for 2026 FIFA.

LocationValueCheck-in

Top guest favorite
A seating area is presented with two comfortable chairs and a small table, illuminated by natural light from large windows. The space features a mounted television on the wall and a simple white bed with a light blanket, creating a relaxing ambiance.
Guesthouse in Media
4.99 out of 5 average rating, 94 reviews

Scenic Farmhouse Escape in Media

Discover your hideaway behind an 1811 stone farmhouse, set on 2 scenic acres with trails, wildlife, and a garden paradise. A 2021 conversion turned this woodshop into a rustic studio with modern comforts—queen bed, full kitchen, 65" Roku TV, washer/dryer, and a private patio. Enjoy tranquility and nature, minutes from vibrant downtown Media and a short drive to Philadelphia. Ideal for a peaceful retreat or city exploration. Book your stay for a perfect blend of convenience and countryside charm!

LocationValueQuiet

Top guest favorite
A bright bedroom features a queen-size bed with plush bedding and decorative pillows. A wooden dresser with a mirror and two lamps are positioned alongside. Natural light filters through the window, highlighting a cozy armchair in the corner. Two doors lead to adjoining spaces.
Guest suite in Wilmington
4.99 out of 5 average rating, 299 reviews

Private Suite & sitting room in Brandywine Valley

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.

FamilyValueQuiet

Top guest favorite
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, 330 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.

FamilyLocationBiking

Guest favorite
Apartment in Prospect Park
4.9 out of 5 average rating, 240 reviews

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

Feel at home in this beautifully renovated private first-floor apartment, ideally located in a quiet suburban neighborhood with easy access to local attractions, restaurants, shopping, & major roadways. This spacious 2BR/1BA apartment is equipped with everything you need for a relaxing stay. Enjoy a private entrance, fast Wi-Fi, contactless self check-in, Smart TVs in bedrooms & living room, & the comfort of an in-unit washer & dryer. The fully equipped kitchen makes it easy to prepare meals.

LocationFamilyNearby

Superhost
The front entrance of the row home features a white door with a large stone archway above. A set of steps leads to the door, flanked by an iron railing. The brick facade is complemented by white window frames, conveying a traditional residential charm.
Home in Chester
4.68 out of 5 average rating, 116 reviews

The Butler Pride

This is and corner property fenced row home, very nice house okay block. Parking can be a challenge at times but otherwise the other amenities especially being so close to interstate 95 and the city of Philadelphia outweigh the parking issue. NOTICE: As per (COVID-19) safety, cleaning, and sanitizing requirements, This home has been thoroughly cleaned and sanitized by the owners clean up crew. Also for your convenience included are disinfectant spray and wipes. Close to PHL airport+stadiums.

FamilyValueCleanliness

Guest favorite
The exterior of the Woodlyn single-family home is showcased with a neatly maintained garden featuring various shrubs and plants. Stone steps lead to the entrance, framed by green trees and a clear blue sky, providing a welcoming first impression.
Home in Woodlyn
4.91 out of 5 average rating, 45 reviews

Comfy, Cozy Home by Philly, Airport, I-95, + more!

This charming Woodlyn single will feel like home away from home. Conveniently located off of I-95, trips to Philadelphia, stadiums, or airport are quick & easy. The spacious home sleeps 4 comfortably w/ 2 bedrooms and 2 full bathrooms! Full kitchen, cozy living room, dining room, office, wifi, w/d, and treadmill included! Enjoy the outdoors on the balcony off the master bedroom and bring your furry friends too! NOTE: 5 ⭐️ reviews under previous account (attempting to recover) & elsewhere!

ValueLocationParks

Guest favorite
Apartment in Northern Liberties
4.92 out of 5 average rating, 119 reviews

Immaculate 1 BR w/ Roof Deck|Old City|Premium View

Complete your Philly experience at The Edison. This modern building contrasts beautifully with Old City — known as the country's most historic square mile. Walk to top restaurants, shops, Independence Hall, the Liberty Bell, Race Street Pier, and more! Just a 10 min Uber to Eagles, Phillies 76ers & Flyers games. ➢Queen Bed ➢Queen Sleeper sofa (linens provided) ➢$20/ day parking in nearby lot ➢Shared rooftop deck with panoramic views ➢Workspace ➢In-unit washer/ dryer ➢24/7 Guest Support

ValueLocationView

Top guest favorite
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
4.98 out of 5 average rating, 363 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

LocationFamilyHiking

Top guest favorite
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, 275 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.

ValueLocationWalkability

Top guest favorite
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
4.98 out of 5 average rating, 122 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

LocationValueQuiet

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
4.76 out of 5 average rating, 339 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!

FamilyLocationWalkability

Popular amenities for Chester vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Chester

Superhost
A spacious living area is furnished with a dark sectional sofa adorned with orange accent pillows. A central coffee table sits on a colorful area rug, with two side tables positioned nearby. Natural light filters in through a large window, enhancing the room's modern design.
Home in Chester
4.69 out of 5 average rating, 42 reviews

Cozy & Modern Rancher Style Home

FamilyLocationComfort

Guest favorite
Home in Prospect Park
4.95 out of 5 average rating, 20 reviews

Modern Luxury in Prime Location

FamilyLocationQuiet

Superhost
A welcoming living area features a large sectional sofa adorned with decorative pillows. The space is highlighted by a wooden accent wall, a large mirror, and natural light streaming through multiple windows covered by dark curtains.
Apartment in Folsom
4.9 out of 5 average rating, 30 reviews

Delco’s Rustic Hideaway!

LocationFamilyAccuracy

Top guest favorite
Home in West Chester
5.0 out of 5 average rating, 15 reviews

South Bridge Farm Cottage

ValueFamilyBreakfast

Top guest favorite
An open living area showcases vaulted ceilings with exposed wooden beams. A light gray sectional sofa is positioned near a coffee table, while a flat-screen TV is mounted on the wall opposite. Soft sunlight illuminates the space, enhancing the inviting atmosphere.
Home in Swarthmore
5.0 out of 5 average rating, 34 reviews

Swarthmore Guesthouse · Walk to College & Train

LocationFamilyWalkability

Superhost
A modern three-bedroom home is showcased, featuring a two-story design with a contrast of grey siding and red shutters. A covered porch is visible at the front, complemented by well-maintained landscaping and greenery surrounding the structure.
Home in Morton
4.66 out of 5 average rating, 134 reviews

Modern 3 bedroom home with finished basement.

LocationValueIndoor spaces

Guest favorite
Home in North Claymont
4.93 out of 5 average rating, 41 reviews

The Cozy Inn! N. Wilmington w/ Queen Bed

LocationValueWalkability

Guest favorite
Condo in Wilmington
4.97 out of 5 average rating, 39 reviews

Mod 1BR Downtown |SofaBed| FreePark|Near Hospital

FamilyLocationAccuracy

When is the best time to visit Chester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$14,638 GYDG$14,638 GYDG$15,056 GYDG$15,056 GYDG$23,003 GYDG$17,984 GYDG$14,638 GYDG$14,638 GYDG$14,638 GYDG$14,638 GYDG$14,638 GYDG$14,638 GYD
Avg. temp1°C2°C6°C13°C18°C23°C26°C25°C21°C15°C9°C4°C

Frequently Asked Questions

  • What are the best places to stay in Chester?

    Consider staying near the waterfront or in residential neighborhoods for a quieter atmosphere. Areas around local parks or main streets often have convenient access to shops, dining, and community events.

  • What are the best things to do in Chester with kids?

    Kids often enjoy playgrounds at local parks, visits to interactive museums, and seasonal community festivities. Family-friendly restaurants and hands-on art workshops are also popular, especially during school holidays.

  • What are some of the best things to do in Chester?

    Explore the waterfront parks, attend local arts events, and learn about Chester’s history at cultural sites. Community festivals, sports matches, and family-run restaurants are also frequently suggested experiences.

  • How is the weather in Chester?

    Chester has cold winters with temperatures around 26–41°F (-3–5°C) and warm, fairly humid summers near 70–88°F (21–31°C). Rain is distributed throughout the year, so carrying an umbrella or waterproof jacket is suggested.

  • When is the best time to visit Chester?

    Late spring through early fall is often recommended for a visit to Chester, with comfortable temperatures and outdoor community events. Autumn brings colorful foliage across parks and riverfront areas.

  • What are the best places to visit in Chester?

    Popular places include riverfront parks, public art installations, and museums with exhibits on local history and culture. The city’s main squares and gathering spaces are also known for their community activities.

  • What are some hiking trails in Chester?

    Some parks in Chester have walking and biking paths suitable for gentle hikes and nature exploration. Trails along the river or within larger green spaces invite visitors to experience local flora and scenic views.

  • What are some family activities we can do in Chester?

    Families can explore parks with playgrounds, enjoy interactive exhibits at museums or visit community recreation centers. Seasonal festivals, sports events, and local libraries often have programming for children of different ages.

  • What are some of the best day trip ideas from Chester?

    Day trips often include exploring museums, gardens, or historic sites in nearby cities and towns, as well as coastal parks or scenic nature preserves around the region. Many visitors enjoy discovering local markets and seasonal festivals just outside Chester.

  • Are there any pet friendly accommodations available in Chester?

    Many accommodations in Chester welcome pets, especially in residential neighborhoods and near local parks. It’s often suggested to review listings for specific pet policies and nearby outdoor spaces for walks.

  • What are some local tips for visiting Chester?

    Travelers frequently enjoy attending local events or markets to connect with the Chester community. Consider exploring beyond main streets to discover parks and hidden art, and check schedules for cultural or sports activities.

  • What is Chester known for?

    Chester is known for its rich industrial history, ties to the early colonial era, and vibrant local arts and community traditions. The city has riverside parks, historic neighborhoods, and sports facilities that draw residents and visitors alike.

  • What are the best hidden gems to explore in Chester?

    Explore local parks along the river, discover murals and public art around downtown, or visit neighborhood community centers hosting events and workshops. Some travelers enjoy searching for unique eateries or historic sites that highlight Chester’s lesser-known stories.

  • What are the best foods to try in Chester?

    Local favorites include hoagies, cheesesteaks, and soft pretzels, reflecting regional Philadelphia-area flavors. Travelers often find soul food, family-run bakeries, and seafood dishes as part of the area’s culinary traditions.

  • What should I bring for a trip to Chester?

    Pack comfortable walking shoes for exploring parks and local sites, and bring a rain jacket, as weather can be unpredictable. In cooler months, layers and a warm coat are useful, especially from November through March.

  • What is the nightlife in Chester like?

    Chester’s nightlife features neighborhood bars, lively community venues, and occasional live music events. Some visitors enjoy sports venues or local restaurants with evening gatherings and entertainment.

  • What are the most popular events or festivals in Chester?

    Chester hosts community parades, cultural celebrations, and seasonal fairs throughout the year. Juneteenth events, summer concerts, and neighborhood gatherings are frequently suggested for experiencing local culture.

  • Are there family friendly vacation rentals in Chester?

    Chester has a variety of family-friendly vacation rentals, including entire homes and apartments in residential neighborhoods. Many options provide kitchens, extra space, and amenities suited for families traveling with children.

Destinations to explore