Chester Holiday Rentals

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Holiday Rentals in Chester

Hope House - Christian Retreat

Eastman
10.0 out of 10, Exceptional, (20)
"Amazing property. Very relaxing. No distractions. "
United States
Marcia D.
Hope House - Christian Retreat

Genesis House - Christian Retreat

Eastman
10.0 out of 10, Exceptional, (45)
"Amazing place to stay for a family getaway! Enjoyed the nature, kayaks on the pond, fishing, and no screens. "
United States
Matthew C.
Genesis House - Christian Retreat

Cheerful cozy lake retreat - Newly Renovated in 2025 - New Floors and New HVAC

Dudley
10.0 out of 10, Exceptional, (1)
"Exellent!!!!! Peaceful and quiet retreat. Just far enough into the country yet close enough to town. Property is more than accommodating. Everything was above and beyond our expectations. Customer service is top- notch!!!!!! Excellent place to just leave all your cares behind and relax and enjoy. An Amazing Gem!!!!! Look this one up for your next adventure, will not disappoint."
United States
Denise L.
Cheerful cozy lake retreat - Newly Renovated in 2025 - New Floors and New HVAC

The Sweet Pea Tiny Home

2.0 star property
Danville
10.0 out of 10, Exceptional, (1)
"Very nice place and the tiny home was well-taken care of."
United States
Jesus Q.
The Sweet Pea Tiny Home

Country Pool House Cottage

Cochran
10.0 out of 10, Exceptional, (7)
"Wonderful place out in the country! A great place to stay!"
United States
Thad F.
Country Pool House Cottage

The Rosebud Tiny Home

Danville
10.0 out of 10, Exceptional, (1)
"Excellent place to rest and reset. The property was Beautiful, the Farm is the Bonus. I woke up every morning to a beautiful sunrise & animal sounds which was therapeutic. Me & my Husband highly recommend."
United States
Tamara
The Rosebud Tiny Home

Revelation House

2.0 star property
Eastman
9.6 out of 10, Exceptional, (5)
"Nice quite place. Great to unwind and the host was very attentive. I would definitely stay there again."
United States
Michelle M.
Revelation House

Silo on the farm

Danville
10.0 out of 10, Exceptional, (1)
Silo on the farm

Unplug and unwind in this tiny home featured on Season 1 HGTV Tiny house hunter.

Danville
10.0 out of 10, Exceptional, (1)
"A place to get away like no other. Perfect if you want privacy and full quietness from the outside world. Plus it’s beyond beautiful "
United States
Luis
Unplug and unwind in this tiny home featured on Season 1 HGTV Tiny house hunter.

Daisy One of a kind Tiny home

Danville
10.0 out of 10, Exceptional, (2)
"The most relaxing stay I've ever had. Thank you"
United States
Christopher
Daisy One of a kind Tiny home

The Jasper Tiny Home

Danville
10.0 out of 10, Exceptional, (1)
"In sweet little Danville, GA you’re looking at a population of less than 300 people which makes this little place the perfect space to get away! My husband and I stocked up on our favorite junk foods and enjoyed just spending time together. The property has no WiFi but they do have TV for you & it was perfect to kinda be off the grid. We also enjoyed walking around the property and petting the horses/donkeys. It was a sweet getaway and sweet time with the Lord and my husband!"
United States
Leah J.
The Jasper Tiny Home

Charming 3-bedroom house with WiFi, AC in Eastman

Eastman
Charming 3-bedroom house with WiFi, AC in Eastman

The Cottage on 5th

3.0 star property
Eastman
The Cottage on 5th

Delightful Two Bedroom Vacation Home on River Side

Dublin
Delightful Two Bedroom Vacation Home on River Side

The Bellevue House

Dublin
The Bellevue House

River side retreat, whole house

Dublin
River side retreat, whole house
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Find out more about Chester

Everything you need to know about Chester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chester has to offer?

Hope House - Christian Retreat: This holiday home rental outside of Chester is located on the waterfront, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Chester?

While exploring the area, visit the sights like Southern Pines Water Park & Regional Park, Middle Georgia College Aviation School and Dublin Mall. Dodge County Golf Club and Oconee Fall Line Technical College are a couple of places you'll find in the wider area.

What are holiday rentals like in Chester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester. Holiday rentals feature extras such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a family getaway.