Chester Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Chester

Lakeside Getaway on Lake Madison. Hot tub with a view of the lake!
Lakeside Getaway on Lake Madison. Hot tub with a view of the lake!
10.0 out of 10, Exceptional, (4)
"Clean, well stocked, beautiful view of lake, direct access to lake. Decor is warm and welcoming and the hot tub, firepit amd other amenities, game room made it a full family one stop vacation"
Lakeside Getaway on Lake Madison. Hot tub with a view of the lake!
Welcome to Millie’s on Lake Madison, a quiet and peaceful family getaway!
Property grounds
Welcome to Millie’s on Lake Madison, a quiet and peaceful family getaway!
9.8 out of 10, Exceptional, (33)
"It was our second time staying Here and we enjoyed our time there and being next to the lake ."
Welcome to Millie’s on Lake Madison, a quiet and peaceful family getaway!
Madison gem by DSU & the Airport! Clean & Packed with Charm by A1Day1
Interior
Madison gem by DSU & the Airport! Clean & Packed with Charm by A1Day1
Madison gem by DSU & the Airport! Clean & Packed with Charm by A1Day1
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Skeet's Retreat: A Hidden Gem of Adventure and Relaxation on Lake Herman!
Exterior
Skeet's Retreat: A Hidden Gem of Adventure and Relaxation on Lake Herman!
Skeet's Retreat: A Hidden Gem of Adventure and Relaxation on Lake Herman!
Beautiful year round lake home! Sleeps 8 comfortably!
Fridge, microwave, oven, stovetop
Beautiful year round lake home! Sleeps 8 comfortably!
10.0 out of 10, Exceptional, (15)
"Pictures and description matched property. Recently updated inside. Was a nice trip."
Beautiful year round lake home! Sleeps 8 comfortably!
Cozy lake house with private sand beach right on Lake Madison
Property grounds
Cozy lake house with private sand beach right on Lake Madison
10.0 out of 10, Exceptional, (8)
"We had a great time at the lake house. Plenty of room, nice and clean, with a big covered deck and a beautiful view of the lake and the sunset. Owners were kind and very responsive when we needed something. The whole experience was hassle-free."
Cozy lake house with private sand beach right on Lake Madison
Unique Home Where The Buffalo Roam! Perfect for Families, Reunions. Hunters.
TV, books
Unique Home Where The Buffalo Roam! Perfect for Families, Reunions. Hunters.
9.4 out of 10, Exceptional, (33)
"A perfect place for a large family group. Saw some buffalo too! Our 2nd time to stay in this rustic home!"
Unique Home Where The Buffalo Roam! Perfect for Families, Reunions. Hunters.
Lake Madison Condo
Outdoor dining
Lake Madison Condo
10.0 out of 10, Exceptional, (39)
"Light on cookware and kitchen items in general. Ice maker did not work. Bathroom is really small. The living room was spacious and relaxing. Beautiful location. Overall, we enjoyed our stay and would consider staying again, but would explore other options in the general area as well."
Lake Madison Condo
WATERFRONT HOME ON LAKE MADISON
Beach towels
WATERFRONT HOME ON LAKE MADISON
10.0 out of 10, Exceptional, (18)
"House was great! AC was awesome, steps from a park and great community. Owners were very accommodating on our request to extend our stay. Highly recommend."
WATERFRONT HOME ON LAKE MADISON
Sportsman's Outpost
2 bedrooms, free WiFi, bed sheets
Sportsman's Outpost
Sportsman's Outpost
Lakefront Fun
Property grounds
Lakefront Fun
9.8 out of 10, Exceptional, (8)
"Beautiful spot on lake Madison! We loved this spot! Perfect for relaxing and having fun!"
Lakefront Fun
Beautiful large lake home for a family retreat, have fun by the water!
Property grounds
Beautiful large lake home for a family retreat, have fun by the water!
Beautiful large lake home for a family retreat, have fun by the water!
Don't see what you're looking for?
See all available properties in Chester
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.

Other types of properties in Chester you may be interested in

Royal River Casino and Hotel
Lobby sitting area
Royal River Casino and Hotel
3.0 star property
8.4 out of 10, Very good, (374)
"Little outdated. But nice to have a room to sleep in."
The price is HK$742
HK$940 total
includes taxes & fees
1 Jul - 2 Jul
Royal River Casino and Hotel
AmericInn by Wyndham Hartford SD
Exterior
AmericInn by Wyndham Hartford SD
2.5 star property
9.2 out of 10, Wonderful, (585)
"Clean, nice pool and comfortable rooms "
The price is HK$935
HK$1,016 total
includes taxes & fees
7 Jul - 8 Jul
AmericInn by Wyndham Hartford SD
AmericInn by Wyndham Madison SD
Reception
AmericInn by Wyndham Madison SD
2.5 star property
8.4 out of 10, Very good, (240)
"The hotel was good but could use a little TLC. Disappointed there wasn’t a fitness room."
The price is HK$766
HK$848 total
includes taxes & fees
30 Jun - 1 Jul
AmericInn by Wyndham Madison SD
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.

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

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 can I see and do in Chester?

While you're exploring the area, Brant Lake and Lake Madison are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Dakota State University and Lake Herman State Park.

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 offer amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a family getaway.

Recent reviews of Chester properties
Expedia verified reviews

AmericInn by Wyndham Hartford SD

AmericInn by Wyndham Hartford SD

5/5 Excellent
"Clean, nice pool and comfortable rooms "
A verified traveller stayed at AmericInn by Wyndham Hartford SD
Posted 4 days ago
AmericInn by Wyndham Hartford SD