Photo by A Jaunt With Joy

Chester Vacation Rentals

    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

In two weeks
In two months
In three months
In four months

Browse Select Chester Vacation Homes

Our top choices for Chester vacation homes

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

9.4 out of 10, Exceptional, (18)
"My daughters loved the big comfy beds. Nice stay. Will visit this place again. Highly recommend. "
The price is CA $147
CA $552 total
includes taxes & fees
Aug 25 - Aug 26
Boho Bliss |2 Bd/1Bth Top Floor Unit | King Beds | 5 Min. Walk to Winthrop

Luxury Carriage House Suite on the Lake.

10.0 out of 10, Exceptional, (12)
"Lovely views- well equipped"
The price is CA $179
CA $230 total
includes taxes & fees
Sep 14 - Sep 15
Luxury Carriage House Suite on the Lake.

The Cozy Gray House

The Cozy Gray House

The Little Lemon Studio | King Bed | Office Space | Walk to Winthrop

9.0 out of 10, Wonderful, (8)
"Will return to this location, Very very well kept and nice."
The price is CA $121
CA $456 total
includes taxes & fees
Sep 9 - Sep 10
The Little Lemon Studio | King Bed | Office Space | Walk to Winthrop

Old Yeller - Renovated House in Aragon c.1906 Near Winthrop & Glencairn Garden

9.6 out of 10, Exceptional, (17)
"This was a great location, so easy to get into Charlotte and other areas. The house was immaculate with plenty of towels and comfortable beds. Would stay here again."
The price is CA $188
CA $383 total
includes taxes & fees
Aug 24 - Aug 25
Old Yeller - Renovated House in Aragon c.1906 Near Winthrop & Glencairn Garden

North Spruce and Main

9.4 out of 10, Exceptional, (41)
"Great place to stay for the weekend!"
The price is CA $194
CA $381 total
includes taxes & fees
Sep 23 - Sep 24
North Spruce and Main

The Garden Spot - Next to Glencairn Garden, near Winthrop & RH indoor sport

9.6 out of 10, Exceptional, (31)
"It was cute and private. Beautiful garden right by the property"
The price is CA $194
CA $390 total
includes taxes & fees
Aug 27 - Aug 28
The Garden Spot - Next to Glencairn Garden, near Winthrop & RH indoor sport

Tree House feel overlooking Glencairn Gardens

10.0 out of 10, Exceptional, (11)
"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 CA $187
CA $381 total
includes taxes & fees
Aug 27 - Aug 28
Tree House feel overlooking Glencairn Gardens

Dream Weaver is a large renovated mill house

9.2 out of 10, Wonderful, (10)
"Had a lovely stay, no issues, smooth process overall"
The price is CA $202
CA $401 total
includes taxes & fees
Aug 24 - Aug 25
Dream Weaver is a large renovated mill house

The Mill Hippie- Renovated in Aragon c.1940 Near Winthrop & Glencairn Garden

9.4 out of 10, Exceptional, (51)
"Loved staying at this house! Everything was as advertised! Great location and a adorable older home! Would definitely recommend! "
The price is CA $194
CA $390 total
includes taxes & fees
Aug 27 - Aug 28
The Mill Hippie- Renovated in Aragon c.1940 Near Winthrop & Glencairn Garden

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 CA $174
CA $352 total
includes taxes & fees
Aug 26 - Aug 27
The Cottage on Shurley

Milton House Cozy and Elegant 3/2

10.0 out of 10, Exceptional, (7)
"It was great!"
The price is CA $278
CA $531 total
includes taxes & fees
Sep 9 - Sep 10
Milton House Cozy and Elegant 3/2

The Restful Retreat | 1Bed/1Bth Home | King Bed | Luxury Bath

10.0 out of 10, Exceptional, (6)
"Great, quiet spot and excellent communication!"
The price is CA $192
CA $553 total
includes taxes & fees
Sep 23 - Sep 24
The Restful Retreat | 1Bed/1Bth Home | King Bed | Luxury Bath

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

9.0 out of 10, Wonderful, (26)
"Spectacular stay!"
The price is CA $195
CA $395 total
includes taxes & fees
Aug 26 - Aug 27
Loco Motive- Renovated House in Aragon c.1940 Near Winthrop & Glencairn Garden

Enchanted forest hotel

The price is CA $400
CA $1,769 total
includes taxes & fees
Aug 24 - Aug 25
Enchanted forest hotel

Lakefront Retreat - Sleeps 18 - Kayaks + Hot Tub

9.8 out of 10, Exceptional, (10)
"We had a great stay at this property! Property is well maintained and great layout for a group. Loved the patio for just hanging out. 100% recommend this house if you are in area!"
The price is CA $672
CA $1,718 total
includes taxes & fees
Aug 24 - Aug 25
Lakefront Retreat - Sleeps 18 - Kayaks + Hot Tub
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