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.

0 of 0 items showing

1 of 3 pages

Top guest favourite

Cottage in New Holland

4.99 out of 5 average rating, 165 reviews

Exquisite cottage with valley views and Hot Tub

SarahRating, 5 stars2 weeks ago

John was great to work with and worked with us to meet our needs as we, unfortunately, were in town for a funeral. The house was great and had everything we needed. We appreciated very much the flexibility that John offered.

Top guest favourite

Cottage in North East

5 out of 5 average rating, 29 reviews

Charming Waterfront Cottage w Private Boat Dock

GraceAnnRating, 5 stars1 week ago

My husband and I wanted to get out of Philly for the weekend and we found Tara’s place last minute. The weather was rainy and cold but the cottage was still a perfect getaway for us! The view of the water by the backyard, the fully stocked kitchen, the comfy couch and king bed were just perfect! We hope to come back!

Top guest favourite

Flat in Chesapeake City

5 out of 5 average rating, 16 reviews

The Pearl: a 70s vibe, hip/cozy

DianaRating, 5 stars1 week ago

The enchanting town of Chesapeake city washes over your starting with check in at the pearl. Watching and tracking ships through the channel or finding the best locals night and party marina vibe added to the experience. Lovely walks and runs in the area Thank you

Top guest favourite

Home in North East

4.96 out of 5 average rating, 46 reviews

Boho River Cottage

StaceyRating, 5 stars6 days ago

Our stay at Cece's Boho Cottage was excellent. It started with an egg hunt around the yard for my boys along with some sweet treats for all to enjoy. Cece gave amazing restaurant suggestions along with local hikes and shops. If you happen to forget something, Cece thought of it! We loved morning coffee on the back porch with the rising sun, comfy beds, and enough space to spread out. Thank you for sharing your adorable cottage with us! We are already trying to plan a trip back!

Guest favourite

Flat in Bryn Mawr

4.93 out of 5 average rating, 258 reviews

+Restaurants Coffee Colleges+ Bryn Mawr Has It All

NickRating, 5 stars2 weeks ago

Overall very nice place to stay. Convenient location near to Bryn Mawr College and downtown. The apartment was clean and comfy. Dave was very responsive whenever we needed help and responded almost immediately, which was especially helpful when my 18-yo daughter got locked inside her bedroom accidentally (the lock on the door probably should be replaced). Dave coached us over the phone on how the gently jimmy the door without breaking anything.

Guest favourite

Guest suite in Center City

4.92 out of 5 average rating, 418 reviews

Center City: Safe, Private, Walkable!

BrianRating, 5 stars1 day ago

This is my third time at Jesse's place and definitely not the last. The location is perfect, close to everything Philly has to offer. The space is perfect for reaxing after a long day wandering the old city and there are plenty of great places to have a drink and a bite to eat. The room is clean, quiet, private and comfortable and Jesse is a great host. I can't recommend it enough.

Top guest favourite

Cottage in Charlestown

4.98 out of 5 average rating, 101 reviews

Blue on the Bay

AndrewRating, 5 stars5 days ago

We loved staying here. The location is beautiful and just a few doors down from the beach. The place was perfectly sized and clean. As a plus, Monica surprised us with a birthday bottle of wine and balloons as a gift. I highly recommend staying here!

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Chester holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Chester's top sights

Linvilla Orchards15 locals recommend

Portobello Cafe6 locals recommend

Wawa4 locals recommend

Other great holiday rentals in Chester

Superhost

Home in Pennsauken Township

5 out of 5 average rating, 3 reviews

Conveniently Located - New Luxury Townhome

RachelRating, 5 stars3 weeks ago

We loved our extended stay here. Bare bones house but exactly what was pictured. The shower in the en-suite is fantastic. I would only change the window treatments in the main bedroom they are too small to actually block the sun. Also the pool table is not full size and there are no tables to put drinks on etc. bring your own mugs too. All in all we had a good time and would stay here again. Thank you!

Guest favourite

Home in Wilmington

4.93 out of 5 average rating, 122 reviews

Five Star Accommodations

BradleyRating, 5 stars1 month ago

Everything as described. It's a beautiful home. We liked having bedroom/full bath on the main level. We were out most of time, but everything in the home was great. If you're looking for a place in Wilmington, this is a great choice. Good communication, too. The home was well stocked with the essentials we like in an Airbnb. You'll be happy here.

Top guest favourite

Home in Medford

5 out of 5 average rating, 8 reviews

Come relax and enjoy 450 feet of lakefront living!

RebeccaRating, 5 stars3 months ago

I so enjoyed the quiet beauty of this hidden gem in the woods. From the moment I booked, Jen was a fabulous hostess, giving thought and care to ensure a positive experience. The home is beautiful, and I was happily surprised by the gorgeous holiday decor and cheer. Everything was just as described, and I couldn't have felt more at home. Having grown up nearby, I have no doubt this would be an oasis in the summer months, though even with ice on the lake, it offered peace and beauty. The beds were ridiculously comfortable, and the warmth of my host permeated the entire home. I recommend it to anyone seeking nature, beauty, and comfort.

Superhost

Home in Point Breeze

4.79 out of 5 average rating, 273 reviews

Lux Escape | Roof Deck w/ Skyline | Patio

QuadriaRating, 5 stars2 weeks ago

I love love love this place it’s amazing we had an amazing time the owner responded soooo fast it was unbelievable I love how she is so caring and helpful this house is 5 star ⭐️ house I’m am most definitely going to book agin for the summer !!!

Guest favourite

Home in Elkton

4.98 out of 5 average rating, 89 reviews

Cami’s Cottage - EV Charger

RobRating, 5 stars3 weeks ago

The cottage was a great stay. The location was super convenient for visiting between Delaware and Maryland. The space is clean and very well laid out. Very enjoyable stay!

Guest favourite

Flat in West Philadelphia

4.86 out of 5 average rating, 166 reviews

King size bed condo all cherry wood cabinets/floor

TsiRating, 5 stars4 days ago

Amazing place, super cozy and beautiful inside. The location is great, really close to everything but backs right up to the woods so it feels really peaceful and private. Skeitha was so chill and nice! I definitely want to be back

Top guest favourite