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Holiday Homes in Chester

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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Holiday Homes in Chester

Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop
Enjoy cooking in this well-equipped kitchen with an oven, range hood, and stainless steel appliances.

Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop

9.4 out of 10, Exceptional, (30)
"We were in town for a basketball tournament and found the residence safe and convenient to the location where games were held."
Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop
Charming Downtown Fort Mill Home w/ Large Backyard
Kitchen features stainless steel appliances, gold hardware, and a window with blinds.

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
Stunning 4 Bed House Perfect for Nature Lovers
Relax by the serene pool surrounded by lush trees and a stone wall.

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
Tree House feel overlooking Glencairn Gardens
Cozy living space with a fireplace, sofa, and dining area.

Tree House feel overlooking Glencairn Gardens

9.8 out of 10, Exceptional, (10)
"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 AU$429
includes taxes & fees
10 Aug - 11 Aug
Tree House feel overlooking Glencairn Gardens
The Cottage on Shurley
Charming single-story home with a gabled roof, front porch, and white shutters.

The Cottage on Shurley

9.8 out of 10, Exceptional, (26)
"Everything was exactly as described (we like that) and our dogs loved it. Close to downtown but not too close. We have a habit of rating our stays based on the quality of the shower pressure and hot water. This one will not disappoint. Thanks for a great stay. "
The price is AU$394
includes taxes & fees
2 Aug - 3 Aug
The Cottage on Shurley
Delightful Victorian home with 6 bedrooms in downtown Fort Mill
Stunning entryway with a grand staircase, decorative rug, and elegant chandelier.

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
Loco Motive- Renovated House in Aragon c.1940 Near Winthrop & Glencairn Garden
Surrounded by lush greenery, this serene water feature offers a peaceful retreat.

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

9.0 out of 10, Wonderful, (26)
"Spectacular stay!"
The price is AU$443
includes taxes & fees
3 Aug - 4 Aug
Loco Motive- Renovated House in Aragon c.1940 Near Winthrop & Glencairn Garden
Dock & Home Theater: Pet-Friendly Lake Wylie Home
Terrace/patio

Dock & Home Theater: Pet-Friendly Lake Wylie Home

10.0 out of 10, Exceptional, (2)
"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
Affordable Fun House
Relax by the pool with a slide for easy access, lounge chairs, and a table for a comfortable retreat.

Affordable Fun House

9.4 out of 10, Exceptional, (34)
"Kids loved the bunk room and outdoor activities. Very clean. Well stocked. Great communication. Would stay again!"
Affordable Fun House
4.2-Acre Lakefront– Game Room，Hot Tub & Private Dock !
Enjoy unobstructed views of the surrounding water from this open deck area, featuring benches and a picnic table.

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 !
Lake Wateree Waterfront Home
Relax in a serene outdoor space with a stone floor, surrounded by a white fence and brick pillars, offering a tranquil view of the water and lush trees.

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
Lake Wateree Home W/Covered Porch, Sunset Views & Dock
Relax on the deck overlooking a serene lake or river, surrounded by trees.

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
Dream Weaver is a large renovated mill house
Modern kitchen with stainless steel appliances, microwave, gas stove, and granite countertop.

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
COZY Downtown FORT MILL...1/2 block to MAIN STREET Restaurants* (3 bd, 2 ba)
Relax in this inviting living space with a comfortable sofa, coffee table, and large rug. Enjoy meals at the kitchen bar or dining area.

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)
'The Farmhouse' in Fort Lawn w/ Fire Pit & Deck!
Relax in a cozy living space with a sofa, armchairs, and a TV.

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

10.0 out of 10, Exceptional, (7)
"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
Enjoy a serene view from this outdoor deck overlooking the water.

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

9.8 out of 10, Exceptional, (46)
"You could not ask for a better location on the water! There is so much room on the property and the house was very accommodating for our larger group. Would highly recommend for friends trips, large family trips, etc. Far enough from the big city but close enough to still take an uber to/from the airport and local restaurants. "
7 BR Private Peninsula & Houseboat LUX Isle Beach Lake Panoramic views Hot Tub
Boho Bliss |2 Bd/1Bth Top Floor Unit | King Beds | 5 Min. Walk to Winthrop
Contemporary kitchen with a window above the sink, refrigerator, microwave, and oven.

Boho Bliss |2 Bd/1Bth Top Floor Unit | King Beds | 5 Min. Walk to Winthrop

9.2 out of 10, Wonderful, (17)
"Boho Bliss is absolutely adorable. Clean, close to everything. The kitchen is nicely stocked and the decor is adorable. Kim, the host is excellent with communication. I stayed at the back house a few weeks ago. Parking is easy and the place is a great stay. "
Boho Bliss |2 Bd/1Bth Top Floor Unit | King Beds | 5 Min. Walk to Winthrop
Milton House Cozy and Elegant 3/2
Relax in this stylish living room with a sofa, ottoman, and dining area.

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 . "
The price is AU$695
includes taxes & fees
26 Aug - 27 Aug
Milton House Cozy and Elegant 3/2
Restful Home in a Quiet Cove w Kayaks, SUPs, Dock & Boat Option - Near Charlotte
Escape to a serene lakeside haven with a large house, wrap-around deck, and dock.

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
Charming Modern Farm House-5 min from Sport Center
Enjoy cooking in this kitchen with a large island, microwave, sink, and stove, perfect for preparing meals.

Charming Modern Farm House-5 min from Sport Center

9.6 out of 10, Exceptional, (24)
"Perfect place for a short trip and perfect location for our boys soccer tournament. Neighbors were great and friendly and host was on top of everything and anything. Would absolutely stay again and recommend to anyone looking "
Charming Modern Farm House-5 min from Sport Center
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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