
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$4,184 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.

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.

Nchanted-Luxury unit near Airport w Parking & Yard
Step into style in this cozy 1 bed/1bath 1st floor unit. 2 car driveway. Keypad entry into living room w/ sleeper sofa, work desk, chair & 50 in Samsung smart TV. Kitchen with granite counter is fully equipped w/ everything you need and a breakfast bar to sit and eat meals. Granite is carried onto the bathroom vanity w/ plenty counter & drawer space stocked w/ amenities. BR has queen bed, dresser, walk in closet, smart tv and electric fireplace. Sliding door leads to yard w/ grill and bistro set

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.

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.

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.

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!

Quiet Empty Nest - North Wilmington
Forget your worries in this spacious and serene space. Short drive to train lines for explorers. Bellevue State Park 1 mile away with biking and hiking 27 miles of trails. Rockwood Museum & Brandywine Valley attractions all a short drive. This is the second floor with steeper narrower steps. A private entrance. There are window air conditioners in living room and bedroom. TV is basic with no cable (30+)channels. We look forward to making your stay enjoyable and comfortable

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

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.

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!
Popular amenities for Chester vacation rentals
Other great vacation rentals in Chester

South Bridge Farm Cottage

Roomy apt 20 minutes from Phila

Mod 1BR Downtown |SofaBed| FreePark|Near Hospital

Sweet Solace

Cozy & Modern Rancher Style Home

Swarthmore Guesthouse · Walk to College & Train

Charming Cottage Retreat in N. Wilmington Near I95

The Butler Pride
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$14,643 GYD | G$14,643 GYD | G$15,062 GYD | G$12,551 GYD | G$12,551 GYD | G$12,970 GYD | G$14,643 GYD | G$14,643 GYD | G$14,643 GYD | G$14,643 GYD | G$14,643 GYD | G$14,643 GYD |
| 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
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.
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