Photo by A Jaunt With Joy

Holiday Homes in Chester

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Chester and around

Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop

9.4 out of 10, Exceptional, (29)
"A nice layout with 2 large bedrooms and a nice big kitchen. Hosts were great with communication. Stayed here 2 times. Very close to Winthrop and town. "
Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop

Charming Downtown Fort Mill Home w/ Large Backyard

2.0 star property
9.6 out of 10, Exceptional, (15)
"Stayed there while our home in Fort Mill was being renovated. Super quiet and tranquil environment and was clean and well equipped. Owner was helpful when I locked myself out by mistake… highly recommend!"
Charming Downtown Fort Mill Home w/ Large Backyard

Tree House feel overlooking Glencairn Gardens

9.8 out of 10, Exceptional, (9)
"This property was exactly as advertised. The place was clean, well stocked with essentials and comfy. Will stay again if we're in the area again!"
The price is €240
includes taxes & fees
27 Jul - 28 Jul
Tree House feel overlooking Glencairn Gardens

Stunning 4 Bed House Perfect for Nature Lovers

9.8 out of 10, Exceptional, (6)
"Love love this place our family had an amazing time the location was perfect for us and the hosts were very responsive would stay here again"
Stunning 4 Bed House Perfect for Nature Lovers

Loco Motive- Renovated House in Aragon c.1940 Near Winthrop & Glencairn Garden

9.2 out of 10, Wonderful, (25)
"Spectacular stay!"
The price is €246
includes taxes & fees
27 Jul - 28 Jul
Loco Motive- Renovated House in Aragon c.1940 Near Winthrop & Glencairn Garden

The Cottage on Shurley

9.8 out of 10, Exceptional, (25)
"Very possibly the best vacation rental I have stayed in."
The price is €220
includes taxes & fees
28 Jul - 29 Jul
The Cottage on Shurley

Delightful Victorian home with 6 bedrooms in downtown Fort Mill

2.0 star property
10.0 out of 10, Exceptional, (16)
"Came down to watch the Mayo Bowl. Great place to host the entire family. Close to Charlotte and a lot of great restaurants within walking distance. Enjoyed our stay."
Delightful Victorian home with 6 bedrooms in downtown Fort Mill

Dock & Home Theater: Pet-Friendly Lake Wylie Home

10.0 out of 10, Exceptional, (1)
"This is a beautiful home located on an amazing property directly on the lake! There was plenty of space to accommodate our group of 20 and there was so much to do both inside and outside of this home. From fishing off the dock, to renting a boat, to playing pool in the basement, there are a lot of things that make this a 5 star stay! The communication from the host was great, and they were very accommodating to our request for an early check in and a late check out. We could not be more...
Dock & Home Theater: Pet-Friendly Lake Wylie Home

Lake Wateree Waterfront Home

9.6 out of 10, Exceptional, (14)
"Beautiful place to relax, slow down and just enjoy! Loved our spacious, clean, awesome VRBO!! We fished, kayaked, grilled and had a bon fire!! Recharged!! We will definitely be back!!"
Lake Wateree Waterfront Home

Affordable Fun House

9.4 out of 10, Exceptional, (34)
"Nice place for a family gathering! Very helpful and friendly host. Thanks! we would stay again if we come to the area."
Affordable Fun House

Lake Wateree Home W/Covered Porch, Sunset Views & Dock

9.8 out of 10, Exceptional, (36)
"We had a great time, everything was just how it was listed. Very clean and private. I would definitely stay here again and recommend to family and friends."
Lake Wateree Home W/Covered Porch, Sunset Views & Dock

COZY Downtown FORT MILL...1/2 block to MAIN STREET Restaurants* (3 bd, 2 ba)

10.0 out of 10, Exceptional, (23)
"Wonderful, well appointed property. Clean & beautiful. Well stocked kitchen and the comfiest beds I have ever slept in!"
COZY Downtown FORT MILL...1/2 block to MAIN STREET Restaurants* (3 bd, 2 ba)

Dream Weaver is a large renovated mill house

9.2 out of 10, Wonderful, (10)
"Nice property, location great for us needing to be near Winthrop Uni, very clean. "
Dream Weaver is a large renovated mill house

'The Farmhouse' in Fort Lawn w/ Fire Pit & Deck!

10.0 out of 10, Exceptional, (6)
"The property was cute and had anything and everything we needed! Super clean and relaxing. The property manager was very friendly, and communicated well throughout our stay. We visit the area yearly, and may have found our new spot to stay in."
'The Farmhouse' in Fort Lawn w/ Fire Pit & Deck!

7 BR Private Peninsula & Houseboat LUX Isle Beach Lake Panoramic views Hot Tub

9.8 out of 10, Exceptional, (46)
"Wonderful home for a family vacation. We will definitely be back in the warmer months to take advantage of all the amenities offered with this vacation rental. The Hosts/owners are top notch, super friendly!!!"
7 BR Private Peninsula & Houseboat LUX Isle Beach Lake Panoramic views Hot Tub

4.2-Acre Lakefront– Game Room,Hot Tub & Private Dock !

10.0 out of 10, Exceptional, (6)
"A wonderful place to stay and just enjoy time together as a family!!"
4.2-Acre Lakefront– Game Room,Hot Tub & Private Dock !

Milton House Cozy and Elegant 3/2

10.0 out of 10, Exceptional, (7)
"The house was adorable and in a great neighborhood . This is the best deal on the market . I searched other VRBOs in rock hill and they were more expensive and not nearly as nice as this one . The house is very well appointed. Would love to buy this house . "
Milton House Cozy and Elegant 3/2

Restful Home in a Quiet Cove w Kayaks, SUPs, Dock & Boat Option - Near Charlotte

9.8 out of 10, Exceptional, (9)
"Wonderful 6-night stay at the Lake House! House was very well stocked and the lake was an absolute blast. We kayaked and swam everyday. Loved the art in the house and just relaxed a lot. Chris was an awesome host and incredibly responsive. Definitely would stay again!"
Restful Home in a Quiet Cove w Kayaks, SUPs, Dock & Boat Option - Near Charlotte

4-bedroom house in delightful Chester with WiFi, AC. Enjoy your stay

The price is €406
includes taxes & fees
4 Aug - 5 Aug
4-bedroom house in delightful Chester with WiFi, AC. Enjoy your stay

Near Downtown Waxhaw Mellow Yellow Suite A

9.8 out of 10, Exceptional, (6)
"Had a great stay!"
Near Downtown Waxhaw Mellow Yellow Suite A
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chester Hotel Reviews