Discover Your Perfect Greenfield Vacation Homes

Best Vacation Homes in Greenfield

10.0
Exceptional
(148 Reviews)
4 Guests 2 Bedrooms 1 Bathroom
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
£97/Night For 7 Nights £678
10.0
Exceptional
(7 Reviews)
251.88 ft² 12 Guests 5 Bedrooms 5 Bathrooms
Free Cancellation Bed & Breakfast
  • Fireplace/Heating
  • Balcony/Terrace
  • View
£164/Night For 7 Nights £1,149
9.6
Exceptional
(593 Reviews)
1 Bathroom
Family Friendly Hotel
  • Pool
  • Balcony/Terrace
  • Breakfast
£109/Night For 7 Nights £763
10.0
Exceptional
(137 Reviews)
6 Guests 2 Bedrooms 1 Bathroom
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
£216/Night For 7 Nights £1,513
10.0
Exceptional
(4 Reviews)
383.91 ft² 6 Guests 3 Bedrooms 3 Bathrooms
Bed & Breakfast
  • Hot Tub
  • Balcony/Terrace
  • Breakfast
£65/Night For 7 Nights £456
10.0
Exceptional
(80 Reviews)
6 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Cabin
  • Fireplace/Heating
  • Kitchen
  • Parking
£108/Night For 7 Nights £757
10.0
Exceptional
(76 Reviews)
6 Guests 2 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
£193/Night For 7 Nights £1,351
10.0
Exceptional
(76 Reviews)
900 ft² 6 Guests 2 Bedrooms 1 Bathroom
Family Friendly Cabin
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
£114/Night For 7 Nights £796

Greenfield Luxury Rentals

10.0
Exceptional
(163 Reviews)
9000 ft² 21 Guests 6 Bedrooms 6 Bathrooms
Family Friendly Other
  • Hot Tub
  • Spa
  • Fireplace/Heating
£1,109/Night For 7 Nights £7,765
10.0
Exceptional
(1 Review)
5000 ft² 18 Guests 3 Bedrooms 3 Bathrooms
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
£1,038/Night For 7 Nights £7,263
10.0
Exceptional
(1 Review)
12 Guests 5 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
£526/Night For 7 Nights £3,684
9.2
Exceptional
(12 Reviews)
2000 ft² 12 Guests 3 Bedrooms 3 Bathrooms
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
£508/Night For 7 Nights £3,553
10.0
Exceptional
(7 Reviews)
2500 ft² 10 Guests 5 Bedrooms 3 Bathrooms
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
£497/Night For 7 Nights £3,482
10.0
Exceptional
(1 Review)
1233 ft² 10 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Kitchen
  • Parking
£463/Night For 7 Nights £3,238
7.0
Very Good
(2 Reviews)
1500 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
£457/Night For 7 Nights £3,195
9.8
Exceptional
(34 Reviews)
10 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
£419/Night For 7 Nights £2,931

Greenfield Pet Friendly Vacation Rentals

10.0
Exceptional
(27 Reviews)
1500 ft² 6 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Apartment
  • Fireplace/Heating
  • Pet Friendly
  • Kitchen
£122/Night For 7 Nights £854
10.0
Exceptional
(1 Review)
215.28 ft² 2 Guests 1 Bedroom 1 Bathroom
Couples Retreat House
  • Balcony/Terrace
  • View
  • Pet Friendly
£87/Night For 7 Nights £606
7.2
Very Good
(159 Reviews)
1 Bathroom
Couples Retreat Hotel
  • Fireplace/Heating
  • Pet Friendly
  • Parking
£61/Night For 7 Nights £427
10.0
Exceptional
(22 Reviews)
700 ft² 6 Guests 2 Bedrooms 1 Bathroom
Family Friendly House
  • Fireplace/Heating
  • Pet Friendly
  • Kitchen
£102/Night For 7 Nights £716
New
3196.88 ft² 8 Guests 1 Bedroom 2 Bathrooms
Free Cancellation House
  • Pet Friendly
  • Parking
  • Internet
£216/Night For 7 Nights £1,513
9.8
Exceptional
(61 Reviews)
1000 ft² 6 Guests 2 Bedrooms 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Pet Friendly
  • Kitchen
£122/Night For 7 Nights £851
9.8
Exceptional
(9 Reviews)
4 Guests 2 Bedrooms 1 Bathroom
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
£88/Night For 7 Nights £618
9.4
Exceptional
(26 Reviews)
6 Guests 2 Bedrooms 1 Bathroom
Pet Friendly Cottage
  • Fireplace/Heating
  • Pet Friendly
  • Air Conditioner
£198/Night For 7 Nights £1,383

Greenfield Large Vacation Homes

10.0
Exceptional
(1 Review)
12 Guests 3 Bedrooms 1 Bathroom
Family Friendly Cottage
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
£149/Night For 7 Nights £1,040
New
11 Guests 1 Bedroom 1 Bathroom
House
  • Pet Friendly
  • Parking
  • Air Conditioner
£150/Night For 7 Nights £1,049
New
6100 ft² 31 Guests 10 Bedrooms 3 Bathrooms
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
£343/Night For 7 Nights £2,405
New
27 Guests 9 Bedrooms 4 Bathrooms
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Pet Friendly
£278/Night For 7 Nights £1,942
10.0
Exceptional
(116 Reviews)
1600 ft² 11 Guests 3 Bedrooms 1 Bathroom
Family Friendly Cabin
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
£172/Night For 7 Nights £1,207
10.0
Exceptional
(78 Reviews)
2000 ft² 14 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
£217/Night For 7 Nights £1,520
10.0
Exceptional
(25 Reviews)
1 ft² 16 Guests 4 Bedrooms 4 Bathrooms
Family Friendly Cabin
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
£286/Night For 7 Nights £1,999
10.0
Exceptional
(12 Reviews)
2673 ft² 10 Guests 4 Bedrooms 2 Bathrooms
Ocean View House
  • Fireplace/Heating
  • Ocean View
  • Balcony/Terrace
£410/Night For 7 Nights £2,870

Why Choose Rent By Owner for your Greenfield Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Greenfield

When should you plan your Vacation Rentals stay?

Choosing the right time to vacation here can enhance your experience, as this destination offers different charms and activities throughout the year, making it essential to consider seasonal weather and local events for a memorable stay.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, visitors flock here to enjoy the pleasant weather and vibrant local events, making it an ideal time to book your vacation rentals. The region experiences warm daytime temperatures, perfect for outdoor activities.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to October)

This season offers stunning autumn foliage and comfortable temperatures, attracting travelers seeking scenic beauty and outdoor adventures. It’s an excellent time to secure a cozy accommodation at attractive rates before the peak winter season begins.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Winter (December to February)

The quieter winter months see fewer visitors, providing a peaceful setting for those seeking solitude or a budget-friendly stay. Temperatures are cooler, so packing accordingly will enhance your comfort during your visit.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
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Early Spring (March to April)

Before the main travel crowds arrive, early spring offers a tranquil atmosphere and the chance to enjoy the region’s emerging natural beauty. This is the best time to find affordable vacation rentals with less competition.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Greenfield

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining areas perfect for family meals or entertaining guests amidst the scenic surroundings.
  • Take advantage of spacious yards suitable for outdoor games and relaxation in the fresh air.
  • Relax by private pools or hot tubs available at some properties, ideal for unwinding after exploring the area.
  • Utilize barbecue grills for cookouts that bring everyone together in a casual outdoor setting.
  • Make use of outdoor fire pits to gather around and share stories under the stars.
  • Discover well-maintained gardens or landscaped areas that add to the charm of your stay here.
  • Benefit from outdoor seating arrangements that offer comfort while taking in the picturesque views of the region.
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Family Activities

  • Greenfield Family Fun Center: Enjoy a day of indoor arcade games and activities perfect for children and teenagers alike.
  • The Greenfield Community Park: Relax outdoors in this scenic park featuring playgrounds, walking trails, and picnic areas ideal for family outings.
  • Greenfield Riverwalk: Take a leisurely stroll along the riverwalk to appreciate the natural beauty and serenity of the area with your loved ones.
  • Greenfield Historical Museum: Discover the local history through engaging exhibits that offer an educational experience suitable for all ages.
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Adult Activities

  • Greenfield Historic District: Explore the charming streets lined with well-preserved buildings that showcase the area's rich history and architectural beauty.
  • Skiing at Greenfield Ski Resort: Enjoy a thrilling day on the slopes at this popular destination, perfect for winter sports enthusiasts seeking adventure here.
  • Local Farmers Market: Visit the vibrant market to experience fresh, local produce and artisanal goods, offering an authentic taste of the region.
  • Greenfield Winery Tours: Indulge in guided tastings and learn about regional winemaking traditions in the scenic vineyards nearby.

Greenfield Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Events: Check the area's event calendar to align your stay with local festivals or activities, enhancing your experience of this destination.
  • Explore Nearby Dining Options: Take advantage of the region’s dining scene by seeking out popular local eateries to enjoy authentic cuisine during your visit.
  • Utilize Local Transportation: Familiarize yourself with transportation options in this area to navigate conveniently and make the most of your time here.
  • Book Your Stay Early: Secure your preferred vacation rentals well in advance to ensure availability during peak seasons in this sought-after region.

Transportation Options

  • Greenfield Municipal Airport: This regional airport offers convenient domestic flights and easy access for travelers visiting the area, making it a practical choice for quick getaways.
  • Bus Services: Local bus routes provide affordable transportation options within the region, connecting you to key destinations and amenities in Greenfield.
  • Taxi and Rideshare Services: Reliable taxi companies and rideshare apps like Uber and Lyft are available here, offering flexible transportation options for exploring the neighborhood or reaching nearby attractions.
  • Personal Vehicle Rentals: Renting a car is a popular choice for visitors wanting the freedom to explore the surrounding region at their own pace, with numerous rental agencies conveniently located nearby.

Local Customs Options

  • Local Harvest Festivals: Celebrating the region’s agricultural roots, these festivals showcase fresh produce and traditional dancing, offering an authentic taste of local culture.
  • Historic Courthouse Etiquette: When visiting the area’s historic sites, it’s customary to greet locals warmly and observe respectful silence during ceremonies at the courthouse.
  • Community Parades: During special occasions, you can enjoy vibrant parades filled with marching bands and colorful floats that reflect the area's friendly spirit.
  • Farmers Market Traditions: Supporting local vendors at the farmers market not only provides fresh regional products but also offers a glimpse into the community's close-knit customs.

Frequently Asked Questions About Greenfield?

2. How many vacation rentals have private pools in Greenfield?

There are 10 vacation rentals with private pools near Greenfield. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Greenfield are best for families?

If you are looking for a family-friendly vacation home in Greenfield, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Greenfield:

4. How many Rentbyowner vacation rentals are available in Greenfield?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 174 in the Greenfield area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Greenfield. 

5. What is the cancellation policy for vacation rentals in Greenfield, Illinois?

Cancellation policies vary by listing, so it’s important to review the specific rental details before booking. You can find this information on the property’s page or contact the host directly for clarification.

6. Are there any additional fees I should be aware of when booking a stay in this area?

Additional fees such as cleaning, service charges, or taxes are typically listed during the booking process. Always check the detailed fee breakdown on the reservation page to ensure transparency.

7. How do I confirm availability for my preferred dates in Greenfield?

Availability can be checked instantly through the listing calendar on the property page. If your dates are unavailable, consider reaching out to the host for alternative options or nearby properties.

8. What amenities are commonly available in vacation rentals here?

Most rentals offer essential amenities like Wi-Fi, parking, and kitchen facilities. Specific features such as outdoor spaces or pet-friendly options are detailed in each listing, so review them carefully.

9. What is the process for checking in and out of a vacation rental in this destination?

Check-in and check-out procedures vary by property and are usually detailed in the host’s instructions. Contact the host directly if you need additional guidance or have special requests.

Greenfield Top Rated Vacation Rentals

10.0
Exceptional
(74 Reviews)
5300 ft² 26 Guests 10 Bedrooms 2 Bathrooms
Family Friendly Other
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
£293/Night For 7 Nights £2,053
9.8
Exceptional
(168 Reviews)
4 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Condo
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
£165/Night For 7 Nights £1,152
9.8
Exceptional
(144 Reviews)
2 Guests 1 Bedroom 1 Bathroom
Family Friendly Condo
  • Private Pool
  • Fireplace/Heating
  • Pool
£105/Night For 7 Nights £735
9.8
Exceptional
(70 Reviews)
2 Guests 1 Bedroom 1 Bathroom
Family Friendly Condo
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
£111/Night For 7 Nights £776
9.4
Exceptional
(646 Reviews)
1 Bathroom
Family Friendly Hotel
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
£69/Night For 7 Nights £480
9.4
Exceptional
(210 Reviews)
1 Bathroom
Family Friendly Hotel
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
£186/Night For 7 Nights £1,306
9.1
Exceptional
(154 Reviews)
301.39 ft² 8 Bathrooms
Free Cancellation Hotel
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
£129/Night For 7 Nights £901
9.0
Exceptional
(662 Reviews)
1 Bathroom
Family Friendly Hotel
  • Pool
  • Breakfast
  • Kitchen
£117/Night For 7 Nights £818