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Holiday rentals in Chester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chester

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

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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.
Flat in Swarthmore
4.89 out of 5 average rating, 318 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.
Flat in Prospect Park
4.9 out of 5 average rating, 217 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 spacious dining area is illuminated by natural light, featuring a large table surrounded by six wooden chairs and two upholstered chairs. Large windows draped with light curtains and a decorative chandelier add to the inviting atmosphere. The adjacent kitchen is visible with stone countertops.
Home in West Deptford
5 out of 5 average rating, 285 reviews

702 Mid Atlantic

Single family home located off Interstate 295 convenient to Philadelphia (15 min) and Atlantic City ( 45 min). Professionally landscaped with blue stone patio, deck and water garden in fenced private yard. Located in lovely suburban community along the Delaware River across from the Philadelphia Airport in South Jersey. Spacious for a family of 8 or less with a full kitchen, family room, living room, dining area and sunroom. Must be 25 yrs to book , show ID and be present at check in.

Guest favourite
A modern kitchen features light brown wooden cabinetry and stainless steel appliances, including a gas stove and dishwasher. A round dining table with stylish chairs is positioned near the counter. Granite countertops and a decorative backsplash enhance the space, with natural light highlighting the room.
Home in Prospect Park
4.84 out of 5 average rating, 134 reviews

CoZy Super Clean, Sanitized, Disinfected-PEACEFUL.

Beautiful, cozy, sunny room with a super comfy L-shaped sectional sofa. Super clean and spacious fully equipped Eat-in kitchen with dishwasher, stove, oven, microwave, regular and K-Cup coffee makers, Micro-wave, Toaster, Pots, Pans, Utensils, and Silverware all provided. The apartment includes (2) 43" Flat Screen TVs; streaming HULU-Live, Amazon Prime, Disney Plus.   Also, a little work desk area provided Free washer/dryer access and Free parking, (short-term lease available).

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, 332 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.
Flat in New Castle
4.98 out of 5 average rating, 126 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.

Guest favourite
An open-concept living space is illuminated by natural light from large windows. A dark futon is adorned with orange decorative pillows, complemented by a low coffee table. A lamp provides additional light, while patterned curtains frame the windows. A doorway leads to the entrance.
Flat in Media
4.91 out of 5 average rating, 163 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.

Guest favourite
The living room features a large sectional sofa and a centered ottoman. Natural light enters through two windows, complemented by sheer curtains. A modern television is mounted on the wall, and an abstract painting adds color. A potted plant and decorative items are present.
Flat in Media
4.89 out of 5 average rating, 110 reviews

Lemon St. Retreat

A quaint 2 bedroom apartment located a stones throw from downtown Media (state street). The neighborhood is full of great restaurants, coffee shops, bars and parks. The house has a newly finished front & back deck, a newly finished kitchen and a bathroom with tub perfect for relaxing. Media is the perfect neighborhood for a weekend or week getaway! Train station a couple blocks away, 20 mins from Philly and Philly airport. If in need for longer stays message me 👍🏼

Guest favourite
A cozy living area is presented with a dark grey sectional sofa adorned with orange accent pillows. A colorful rug covers the hardwood floor, and a painting depicting a serene pathway hangs on the wall. Natural light enters through large windows, illuminating the inviting space.
Home in Lansdowne
4.89 out of 5 average rating, 151 reviews

Charming historical home near Philadelphia

This 3 story victorian home sits on a treelined street nestled between a Quaker school and picturesque stone church. The 3rd floor apartment is resident occupied and the 1st and 2nd floors consist of 2+ bedrooms, kitchen, dining room and LR solely for AirBNB guests. Cozy up with a good book, cook a meal in the well appointed kitchen, relax by the outdoor fire pit and find your zen in the garden. Wifi and 2 parking spaces. Welcome to the Honeysuckle Hideout.

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
4.98 out of 5 average rating, 255 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.

Guest favourite
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.
Flat in Media
4.78 out of 5 average rating, 316 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, 574 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 holiday 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 house rentals in Chester?

    Experience the best of Chester with our house rentals, starting at about $20 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 120 vacation rentals in Brookhaven, over 120 vacation rentals in Upland, and over 330 vacation rentals in Woodlyn.

  • Do house rentals in Chester have air conditioning?

    Absolutely! We offer over 20 house 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 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.

  • 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 holiday rentals in Chester

  • Total holiday rentals

    Explore 40 holiday rentals in Chester

  • Nightly prices starting at

    Chester holiday rentals start at £15 per night before taxes and fees

  • Verified guest reviews

    Over 610 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of Chester holiday rentals include wifi 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

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