Chicago\92s Best Vacation Rentals - Vacation Rentals in Pleasant Plains

Luxury 2 Bedroom Spacious House with Huge Backyard From US $135
         

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7.8 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Drury Inn & Suites Springfield IL From US $154
         

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9.4 (1005 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holly & Matt Suite @ Three Pines Petersburg From US $155
         

10.0 (24 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Luxury Places to Stay in Pleasant Plains

Over 287+ Luxury Places to Stay in or Near Pleasant Plains
The Bressmer - Entire House From US $830
         

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9.0 (1 Review)
House
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  • View
Spacious Home w/Games, 4 fireplaces, 5 acres! From US $714
         

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Great for Groups: Home 3 Mi to Dtwn Springfield! From US $680
         

Luxury 6BR Retreat with Fire Pit Sleeps 12 From US $534
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in Pleasant Plains

Over 46+ Top-Rated Vacation Rentals with a Pool in or Near Pleasant Plains
Drury Inn & Suites Springfield From US $168
         

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9.2 (518 Reviews)
Hotel
  • Air Conditioner
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  • Pet Friendly
Northfield Inn Suites and Conference Center From US $143
         

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8.8 (689 Reviews)
Hotel
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  • Parking
  • Pool
Courtyard by Marriott Springfield From US $153
         

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8.8 (650 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Ramada by Wyndham Springfield North From US $101
         

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8.8 (464 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Courtyard by Marriott Springfield From US $130
         

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8.4 (48 Reviews)
Hotel
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  • Parking
  • Pool
Home2 Suites By Hilton Springfield From US $155
         

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8.2 (25 Reviews)
Hotel
  • Air Conditioner
  • Pet Friendly
  • Pool
Comfort Suites near Route 66 From US $133
         

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8.1 (298 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Pleasant Plains

Over 79+ Pet-Friendly Vacation Rentals in or Near Pleasant Plains
Modern Bungalow Home with Mid-Century Flair From US $128
         

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6.8 (36 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Home2 Suites By Hilton Springfield From US $158
         

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8.8 (40 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
The Archer Homestead From US $224
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area
Peaceful Spaulding Orchard Home From US $396
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Completely remodeled, pet-friendly, 'smart' home in the country! From US $144
         

9.8 (99 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Pleasant Plains

Over 22+ Large Vacation Homes & Villas in or Near Pleasant Plains
Historic Bungalow: For Groups & Families Sleeps 11 From US $221
         

9.2 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Bressmer From US $222
         

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9.5 (52 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Spacious & Cozy ~ Mins to Downtown From US $340
         

8.4 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Church of the Periwinkles From US $575
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Pleasant Plains

Over 57+ Wheelchair Accessible Vacation Homes in or Near Pleasant Plains
Microtel Inn&Suites by Wyndham From US $147
         

6.0 (4 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
RiverBank Lodge From US $113
         

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8.8 (57 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
MainStay Suites Springfield IL From US $74
         

5.2 (372 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
The Classic Suite | Amazing View of Governor Mansion From US $118
         

4.7 (10 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
Presidents Retreat | Amazing View of State Capitol From US $155
         

4.3 (7 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
Black Coffee Suite | State Capitol & Med District From US $178
         

3.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible

Pleasant Plains Vacation Rentals and Airbnb Places to Stay Under $200

Over 187+ Pleasant Plains Vacation Rentals and Airbnb Places to Stay Under $200
Charming Springfield Home: 2 Mi to Downtown From US $144
         

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10.0 (3 Reviews)
House
  • Parking
  • Security/Safety
  • Fireplace/Heating
Days Inn by Wyndham Springfield From US $77
         

6.6 (826 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Close to Downtown - 2 queen beds From US $123
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Rainbow Retreat ~ 3-bedroom fun loving home full of color! From US $177
         

9.8 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming Springfield Home: 2 Mi to Downtown From US $197
         

9.6 (25 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Entire apartment close to downtown - 2 Queen beds From US $129
         

9.4 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Pleasant Plains

Over 100+ Instantly Bookable Vacation Homes in or Near Pleasant Plains
Sunflower Cottage From US $233
         

New
House
  • Air Conditioner
  • Parking
  • TV
4 Mi to Capitol: Spacious Springfield Home w/Deck From US $324
         

About Pleasant Plains Vacation Rentals

With more than 296 Pleasant Plains vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Chicagosbestvacationrentals and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Pleasant Plains.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Chicagosbestvacationrentals Pleasant Plains, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Pleasant Plains. Places to stay near Pleasant Plains are 647.97 ft² on average, with prices averaging US $188 a night.

Chicagosbestvacationrentals makes it easy and safe to find and compare vacation rentals in Pleasant Plains with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Pleasant Plains

Type Count
Vacation Homes 130
Hotels 80
Holiday Apartments 74
Cottages 3
B&B 1
Cabin Rentals 1
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Pleasant Plains

Pro Tip: Chicagosbestvacationrentals makes it easy to compare the best listings on Chicagosbestvacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Chicagosbestvacationrentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Pleasant Plains.

Weather in Pleasant Plains

View the weather forecast for Pleasant Plains before booking your Pleasant Plains Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Pleasant Plains Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Pleasant Plains?
How many vacation rentals are available in Pleasant Plains?

Currently, the total number of properties listed in 2026 is over 296 in the Pleasant Plains area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Pleasant Plains.