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Vacation rentals in Chester

Vacation rentals in Chester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • White House Bed
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 shared bathroom
    White House Bed

    Small house located near downtown Madison. Easy walking distance to many bars and restaurants! I am a Youth/College Pastor and am out early in the morning and come back later at night. I look forward to hosting you!

    What guests are saying:

    “This is a sweet and quiet place to stay. The room and house are clean, and there is easy access to the kitchen and bathroom. I only saw Andrew once, and the reat of the time it was quiet. It's winter, so there was some snow and ice to walk around to get to the door. Easy check in with a key code, and wifi worked great! Also he supplied soap and lotion and that was great. Easy walk to downtown-an amazing thrift store and cafes. Overall a tremendous value!”

  • Lake Madison Penthouse Condo
    SUPERHOSTEntire apartment · 4 guests · 2 beds · 1 bathroom
    Lake Madison Penthouse Condo

    This Lake Madison Penthouse condo has breathtaking views of the water unlike any other spot on the lake! This 3rd floor unit offers a large deck to take in the warm sun, cool breeze and gorgeous view of all Lake Madison!

    What guests are saying:

    “Demi is an excellent host. Everything was clean and updated. Comfortable beds and furniture. Everything we needed was there to cook and grill. The restaurant next door was convenient, good food, and excellent mojitos. The 3rd floor deck was a delight from coffee in the morning to cocktails at night.”

  • The Meeting Place
    SUPERHOSTEntire flat · 4 guests · 2 beds · 1 bathroom
    The Meeting Place

    Your very own private apartment. Seven person Hot Tub. Available March 13 through November. Three minutes to the airport and close to Denny Sanford Center for a evening concert, to the Pavilion for a play or musical, and downtown where you will enjoy the cities lights and wonderful restaurants. Ask us about our park and fly program. Just minutes away from The Falls. Two blocks from Veteran's Memorial Park where there is fishing and a swimming pool for the kids, bikes available for your use.

    What guests are saying:

    “We very much enjoyed our stay at Robert and Teresas's airbnb. Teresa was leaving as we arrived so we got to meet her and was very welcoming amd helpful in answering all of our questions. The space was very cute and comfortable and had a lot of nice amenities like a tv with Netflix access, towels for the hot tub, frosted mugs, and fresh filtered water. We enjoyed using the hot tub and the bikes provided for guest use. We were able to take a morning bike ride and explore the town and Falls Park which was very cool ! We would definitely stay again.”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
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Popular amenities for Chester holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chester

Bachelor pad w/ 2 Great Danes
SUPERHOSTPrivate room
Bachelor pad w/ 2 Great Danes
Price:€22 / night
Margaret's Cozy Condo
SUPERHOSTPrivate room
Margaret's Cozy Condo
Price:€32 / night
The Historic Dairy Coach House
SUPERHOSTEntire guest house
The Historic Dairy Coach House
Price:€31 / night
Private House/Duplex
SUPERHOSTEntire house
Private House/Duplex
Price:€71 / night
Shriver Square Guest Suite- in the heart of DTSF!
SUPERHOSTEntire apartment
Shriver Square Guest Suite- in the heart of DTSF!
Price:€53 / night
Southeast Home
SUPERHOSTEntire house
Southeast Home
Price:€58 / night
Inspiration Ranch-cleanliness is our TOP priority!
SUPERHOSTEntire house
Inspiration Ranch-cleanliness is our TOP priority!
Price:€77 / night
Centrally-Located Charmer
SUPERHOSTPrivate room
Centrally-Located Charmer
Price:€41 / night
Lake Home Get Away
SUPERHOSTEntire house
Lake Home Get Away
Price:€216 / night
Entire private lower level  KING BED
SUPERHOSTEntire flat
Entire private lower level KING BED
Price:€52 / night
2BR updated apartment near downtown
SUPERHOSTEntire flat
2BR updated apartment near downtown
Price:€50 / night
Private lower level entirely yours!
SUPERHOSTEntire guest suite
Private lower level entirely yours!
Price:€53 / night
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