Vacation rentals in Chesterland

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chesterland

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Chardon

5.0 out of 5 average rating, 15 reviews

Avonlea Gardens & Inn - Bluebell Suite

Avonlea Inn - Bluebell Suite is half of our inn, a century home with unique vintage charm. The Bluebell Suite offers 1 bedroom (1 queen), living room with queen pullout sofa, & a kitchen. The inn is located on the same property as our peaceful native plant nursery, which you are free to wander! If you would like to rent both the Bluebell Suite and the Rose Suite (the other half of the house), please see our separate listing for the Entire House. Pets are allowed only if renting the entire house.

May 21 – 28

€ 145 per night

Guest favorite

Guesthouse in Chardon

4.93 out of 5 average rating, 153 reviews

Chardon Loft

Large private studio style living area with queen size bed, couch, table/chairs, TV, refrigerator, microwave, hot plate, NO OVEN OR STOVE TOP, sink, large shower, A/C, heat, washer and dryer, and deck. Wifi internet is provided. The television has Netflix. No cable channels are provided. The furnace is nontraditional. It is open and not in a closet. The noise when running and starting will be louder than normal during winter months. Ear plugs are available for those that are noise sensitive.

Sep 16 – 23

€ 85 per night

Guest favorite

Cottage in Burton

4.99 out of 5 average rating, 106 reviews

Relax & Unwind, Lake View on Lt. Punderson Lake

Quiet lake community with views that create a calmness and peacefulness one can hope for in this busy world. Open floor plan with warm golden wood floors, vaulted ceiling, stone fireplace and three sided windowed room with views of the lake. Large outdoor deck for plenty to sit and enjoy the sounds of nature and maybe witnessing an eagle fishing. Light a fire at designated fire-pit for evening gatherings to sit around and make our favorite summer treats, s'mores. If unwinding is your goal...

Oct 16 – 23

€ 264 per night

Guest favorite

Home in Willoughby

4.98 out of 5 average rating, 111 reviews

Retreat at DTW

Come relax & enjoy The Retreat at DTW! Just minutes away from Historic Downtown Willoughby where you can shop, dine & stroll the streets at your leisure. This completely renovated single family ranch home has so much to offer. Including all kitchen appliances, washer & dryer, all necessities (kitchenware, towels, sheets, etc.) & playing cards plus board games for your pleasure. The bedroom has a king bed & living room has a sofa bed. Enjoy the reading nook on the 2nd level loft area & backyard.

Sep 23 – 30

€ 152 per night

Guest favorite

Guesthouse in University Heights

4.98 out of 5 average rating, 223 reviews

Tyndall Carriage House-Private Guesthouse

Price includes cleaning and occupancy fees. Tyndall Carriage House is a quiet and private guesthouse, located in a detached unit behind our home, above the garages. Perfect for a weekend getaway or longer stays. The neighborhood is walk/bike-able, close to John Carroll University, Cedar-Lee District, Fairmount Circle, and Van Aken District with many fun shops and exciting restaurants nearby. A fifteen minute drive takes you to downtown Cleveland, The Cleveland Clinic and other city attractions.

Mar 17 – 24

€ 131 per night

Guest favorite

Cottage in Burton

4.92 out of 5 average rating, 119 reviews

Lakeside Cottage with Views and Charm

This charming & cozy lakeside cottage has gorgeous views & everything you need. The main floor has a spacious living-dining-work area with big windows, fireplace, 55" tv plus a roomy kitchen stocked for cooking. Enjoy sitting & dining on the gated deck. The finished basement is ideal games & kids. Sleep well in the quiet surroundings & black out shades. Stroll the lake, explore Punderson SP, cute towns & Amish country. Come to relax, play & enjoy. Bring your slippers & well-behaved pooches.

Sep 4 – 11

€ 174 per night

Guest favorite

Apartment in Chagrin Falls

4.88 out of 5 average rating, 165 reviews

Cozy Solar Powered Hideaway (Pet Friendly)

Newly built Solar powered 1 BR Private detached garage apartment with loft. This charming pet friendly hideout is situated on a 1.5 acre partially wooded lot. The apartment is equipped with brand new appliances, beautiful wood accents, a cozy loft accessed via ladder, and a wonderful fenced in area for guest dogs! A laundry room is available for guest use in the garage below. Less than 10 min from Chagrin Falls, 30 min to CVNP, 30 min from CLE airport. Convenient keypad entry to apartment.

Jul 5 – 12

€ 120 per night

Guest favorite

Cabin in Solon

4.84 out of 5 average rating, 134 reviews

Cabin in the woods

We have a 900 sq.ft. , log cabin in the woods. The woods of Solon, OH. A southeast suburb of Cleveland. The cabin has 2 bedrooms, each with a queen bed and lots of built in cabinets. They share full bath. As you enter the mud room, to the right is a laundry room with washer & dryer, straight ahead the great room complete with a stone fireplace lots of windows and a small functional kitchen. Welcome to your home in the woods!! We have installed a brand new furnace, keeping the cabin toasty

Sep 16 – 23

€ 156 per night

Guest favorite

Apartment in Burton

4.96 out of 5 average rating, 50 reviews

Maple Syrup Sugarhouse Studio Apartment

Take it easy at this unique and tranquil getaway at Butternut Maple Farm in the heart of Burton Township right by the Geauga County Fairgrounds and just miles from Amish Country. This brand new, fully furnished smoke-free studio apartment is on the top floor of the sugarhouse with a gorgeous second floor deck perfect for your morning coffee. During maple sugar season (January-March), you receive front row seats to watch and/or participate in making our award winning organic maple syrup!

Dec 6 – 13

€ 112 per night

Guest favorite

Cabin in Chardon

4.98 out of 5 average rating, 132 reviews

"Just Breathe"

“Just Breathe” is a cozy log cabin sitting on the shores of a scenic 160-acre lake. It is a peaceful place to clear your thoughts & recharge you soul. Appreciate the joy of spending time doing things that regenerate your personal strength. Whether it is boating, fishing, biking, hiking, reconnecting with nature, or learning a new skill, you can find it here. Personalized Concierge Services are available for each guest to ensure individual preferences are met for a delightful stay.

Aug 28 – Sep 4

€ 198 per night

Superhost

Farm stay in Chardon

4.87 out of 5 average rating, 288 reviews

Bonnie's Guesthouse @ Peridot Equine Sanctuary

***ALL PROFITS SUPPORT THE HORSES OF PERIDOT EQUINE SANCTUARY*** The rustic decor and well lit space reflects the nature of our horse farm & sanctuary, where you can stay for a peaceful country getaway. We're rural, but you'll still have easy access to lots of amenities in the wonderful nearby town of Chardon, less than 10 minutes away. Cleveland itself, currently going through a "rustbelt renaissance" is only about 45 minutes minutes West. We welcome guests of all backgrounds!

Nov 25 – Dec 2

€ 145 per night

Guest favorite

Apartment in Chardon

4.93 out of 5 average rating, 73 reviews

1br-1bth- Furnished Oasis in Chardon

The apartment is above a detached garage. Built within the last 5yrs, the spacious floor plan is modern and fresh. With your own garage spot, on-site laundry, a full kitchen, walk-in closet and large private bathroom, this apartment feels just like home. Long term lease is available for a discounted rate. The apartment is located on a busy street (“busy” for a small town) you will hear cars and motorcycles drive by. Please take this into consideration when booking.

Sep 5 – 12

€ 96 per night