Vacation rentals in Chester, IL

35 available vacation rental offers

airbnbBooking.comVrboExpediaSonderpricelineTripadvisorTrip.comHomestayHotels.comOrbitz

Choose the perfect vacation accommodation

Price per night

Up to $100$100 - 200From $200

Accommodation type

Vacation rentals

Rating

Excellent 9+Very good 8+Good 7+All ratings

Best Vacation rentals and Airbnb offers in Chester, IL

Mudline Lodging your premier Cabin Rental in Southern Illinois! - Chester, IL

Mudline Lodging your premier Cabin Rental in Southern Illinois!

Cabin, Chester

Mudline Lodging your premier Cabin Rental in Southern Illinois! is a cabin in Chester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Mudline Lodging your premier Cabin Rental in Southern Illinois!

Mudline Lodging your premier Cabin Rental in Southern Illinois! is a cabin in Chester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $688.

From$98/night
Show
Crazy Joe's Cabin #1 - Chester, IL

Crazy Joe's Cabin #1

Cottage, Chester

Crazy Joe's Cabin #1 is a cottage in Chester. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Read more

About Crazy Joe's Cabin #1

Crazy Joe's Cabin #1 is a cottage in Chester. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: non smoking, shower, lang::en, and can speak english.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $833.

From$119/night
Show
Cottage w/ Yard, Walk to Historic Attractions - Chester, IL

Cottage w/ Yard, Walk to Historic Attractions

Holiday Home, Chester

Cottage w/ Yard, Walk to Historic Attractions is a holiday home in Chester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About Cottage w/ Yard, Walk to Historic Attractions

Cottage w/ Yard, Walk to Historic Attractions is a holiday home in Chester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and non smoking::room.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,312.

From$120/night
Show
MS Bette’s has added a Hot Tub to our 3 bedroom 1 bath rental! - Chester, IL

MS Bette’s has added a Hot Tub to our 3 bedroom 1 bath rental!

Holiday Home, Chester

MS Bette’s has added a Hot Tub to our 3 bedroom 1 bath rental! is a holiday home in Chester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base…

Read more

About MS Bette’s has added a Hot Tub to our 3 bedroom 1 bath rental!

MS Bette’s has added a Hot Tub to our 3 bedroom 1 bath rental! is a holiday home in Chester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $929.

From$133/night
Show

Best Chester, IL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Stay N Play Cabin Close to Kinkaid Lake - Chester, IL

Stay N Play Cabin Close to Kinkaid Lake

Cabin, Chester

Stay N Play Cabin Close to Kinkaid Lake is a cabin in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Stay N Play Cabin Close to Kinkaid Lake

Stay N Play Cabin Close to Kinkaid Lake is a cabin in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $989.

From$141/night
Show
Beautiful Modern Loft In Wine Country! - Chester, IL

Beautiful Modern Loft In Wine Country!

Apartment, Chester

Beautiful Modern Loft In Wine Country! is a apartment in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country! is a apartment in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,121.

From$160/night
Show
Urban Loft #7 BLUE · Downtown Urban Loft above Restaurants & Boutiques - Chester, IL

Urban Loft #7 BLUE · Downtown Urban Loft above Restaurants & Boutiques

Apartment, Chester

Urban Loft #7 BLUE · Downtown Urban Loft above Restaurants & Boutiques is a apartment in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Urban Loft #7 BLUE · Downtown Urban Loft above Restaurants & Boutiques

Urban Loft #7 BLUE · Downtown Urban Loft above Restaurants & Boutiques is a apartment in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,257.

From$180/night
Show
Downtown Urban Loft above Restaurants - Chester, IL

Downtown Urban Loft above Restaurants

Apartment, Chester

Downtown Urban Loft above Restaurants is a apartment in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Downtown Urban Loft above Restaurants

Downtown Urban Loft above Restaurants is a apartment in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,266.

From$181/night
Show

Best Pet-Friendly Vacation Rentals in Chester, IL

Bring your pet along with stays that welcome four-legged travelers.

Murphysboro Retreat w/ Deck Near Kinkaid Lake! - Chester, IL

Murphysboro Retreat w/ Deck Near Kinkaid Lake!

Apartment, Chester

Murphysboro Retreat w/ Deck Near Kinkaid Lake! is a apartment in Chester, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the…

Read more

About Murphysboro Retreat w/ Deck Near Kinkaid Lake!

Murphysboro Retreat w/ Deck Near Kinkaid Lake! is a apartment in Chester, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,625.

From$177/night
Show
Tranquil and relaxing living quarters surrounded by nature. - Chester, IL

Tranquil and relaxing living quarters surrounded by nature.

Apartment, Chester

Tranquil and relaxing living quarters surrounded by nature. is a apartment in Chester, with pet-friendly space, parking, and a quieter setting. This stay gives travelers a comfortable base…

Read more

About Tranquil and relaxing living quarters surrounded by nature.

Tranquil and relaxing living quarters surrounded by nature. is a apartment in Chester, with pet-friendly space, parking, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,265.

From$181/night
Show
Downtown Loft w/ Amazing Bath Tub & Shower - Chester, IL

Downtown Loft w/ Amazing Bath Tub & Shower

Apartment, Chester

Downtown Loft w/ Amazing Bath Tub & Shower is a apartment in Chester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Downtown Loft w/ Amazing Bath Tub & Shower

Downtown Loft w/ Amazing Bath Tub & Shower is a apartment in Chester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,420.

From$203/night
Show
Murphysboro Retreat w/ Deck Near Kinkaid Lake! - Chester, IL

Murphysboro Retreat w/ Deck Near Kinkaid Lake!

Apartment, Chester

Murphysboro Retreat w/ Deck Near Kinkaid Lake! is a apartment in Chester, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the…

Read more

About Murphysboro Retreat w/ Deck Near Kinkaid Lake!

Murphysboro Retreat w/ Deck Near Kinkaid Lake! is a apartment in Chester, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,458.

From$208/night
Show

Best Chester, IL vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Kat's Get Away by the Lake - Chester, IL

Kat's Get Away by the Lake

Cabin, Chester

Kat's Get Away by the Lake is a cabin in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About Kat's Get Away by the Lake

Kat's Get Away by the Lake is a cabin in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,014.

From$145/night
Show
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses - Chester, IL

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses

Holiday Home, Chester

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses is a holiday home in Chester, with parking, kitchen access, and room for a group. This stay gives travelers…

Read more

About Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses is a holiday home in Chester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,324.

From$189/night
Show
Charming modern farmhouse - four miles from WSRC - Chester, IL

Charming modern farmhouse - four miles from WSRC

Country House, Chester

Charming modern farmhouse - four miles from WSRC is a country house in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Charming modern farmhouse - four miles from WSRC

Charming modern farmhouse - four miles from WSRC is a country house in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,795.

From$256/night
Show
Gorgeous, downtown house! - Chester, IL

Gorgeous, downtown house!

Apartment, Chester

Gorgeous, downtown house! is a apartment in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About Gorgeous, downtown house!

Gorgeous, downtown house! is a apartment in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,312.

From$616/night
Show

Our Favorite Family-Friendly Vacation Rentals in Chester, IL

Plan a trip with stays that give families more room to spread out.

Hickey House - Chester, IL

Hickey House

Cottage, Chester

Hickey House is a cottage in Chester, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family…

Read more

About Hickey House

Hickey House is a cottage in Chester, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: non smoking, lang::en, can speak english, pets::not allowed, and pets not allowed.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,966.

From$281/night
Show
Gorgeous Historic Victorian - 4 bedrooms 2 bathrooms - 4 Blocks Walk to Town - Chester, IL

Gorgeous Historic Victorian - 4 bedrooms 2 bathrooms - 4 Blocks Walk to Town

Holiday Home, Chester

Gorgeous Historic Victorian - 4 bedrooms 2 bathrooms - 4 Blocks Walk to Town is a holiday home in Chester, with kitchen access and room for a group. This stay gives travelers a comfortable…

Read more

About Gorgeous Historic Victorian - 4 bedrooms 2 bathrooms - 4 Blocks Walk to Town

Gorgeous Historic Victorian - 4 bedrooms 2 bathrooms - 4 Blocks Walk to Town is a holiday home in Chester, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,791.

From$399/night
Show
Spacious Shawnee Forest Hideaway! Hilltop Estate - Chester, IL

Spacious Shawnee Forest Hideaway! Hilltop Estate

Cottage, Chester

Spacious Shawnee Forest Hideaway! Hilltop Estate is a cottage in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Spacious Shawnee Forest Hideaway! Hilltop Estate

Spacious Shawnee Forest Hideaway! Hilltop Estate is a cottage in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,176.

From$640/night
Show