Airbnb Properties for Sale in Woodstock, IL

Looking for a vacation rental investment in Woodstock, IL with high ROI ?

Explore a range of newly added short-term rental homes in Woodstock, IL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Woodstock, IL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1109 Wicker St Woodstock, IL Come and see this cute little ranch home and you will love it and want to move right in. ...	3 beds \| 1 baths \| 1,088 sq.ft.	$299,900	Airbnb cash on cash: 4.29% Traditional cash on cash: 3.46% Airbnb Rental Income: $2525 Traditional Rental Income: $1682 Airbnb ROI: 4.29% Traditional ROI: 3.46%
1019 N Madison St Woodstock, IL Imagine yourself living only a short walk from the historic downtown Woodstock, the conven...	2 beds \| 1 baths \| 784 sq.ft.	$215,000	Airbnb cash on cash: 4.91% Traditional cash on cash: 4.29% Airbnb Rental Income: $2093 Traditional Rental Income: $1429 Airbnb ROI: 4.91% Traditional ROI: 4.29%
110 N Seminary Ave Woodstock, IL Two-story home. 3 bedrooms with wood-looking laminated floors. Full basement. Freshly pain...	3 beds \| 1 baths \| 1,125 sq.ft.	$224,900	Airbnb cash on cash: 5.72% Traditional cash on cash: 4.38% Airbnb Rental Income: $2525 Traditional Rental Income: $1630 Airbnb ROI: 5.72% Traditional ROI: 4.38%
434 E Calhoun St Woodstock, IL Three (3) bedroom single family home with huge backyard. New carpets on second floor and n...	3 beds \| 1 baths \| 810 sq.ft.	$220,000	Airbnb cash on cash: 6.48% Traditional cash on cash: 4.31% Airbnb Rental Income: $2525 Traditional Rental Income: $1463 Airbnb ROI: 6.48% Traditional ROI: 4.31%
708 S Rose Farm Rd Woodstock, IL EQUESTRIAN CENTER & HISTORIC HOME----THIS IS A TOTAL TURNKEY LUXURY RIDING ESTATE 20 acres...	5 beds \| 4 baths \| 4,084 sq.ft.	$1,995,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 0.93% Airbnb Rental Income: $7414 Traditional Rental Income: $4706 Airbnb ROI: 1.62% Traditional ROI: 0.93%
15309 Kishwaukee Valley Rd Woodstock, IL Immaculate 5 bedroom home featuring high-end finishes throughout the great open floor plan...	5 beds \| 4 baths \| 7,279 sq.ft.	$1,249,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 2.03% Airbnb Rental Income: $7414 Traditional Rental Income: $5018 Airbnb ROI: 2.87% Traditional ROI: 2.03%
8205 Austin Trl Woodstock, IL Proposed new construction by U.S. Home Builders! This 3,200 sq ft two-story option on the ...	5 beds \| 2 baths \| 3,200 sq.ft.	$949,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 0.55% Airbnb Rental Income: $7414 Traditional Rental Income: $3458 Airbnb ROI: 3.42% Traditional ROI: 0.55%
0000 Lake Shore Dr Woodstock, IL	N/A beds \| N/A baths \| N/A	$300,000	Airbnb cash on cash: 0.39% Traditional cash on cash: -1.49% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: 0.39% Traditional ROI: -1.49%
338 Mchenry Ave Woodstock, IL 338 Mchenry Ave, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$299,000	Airbnb cash on cash: 0.4% Traditional cash on cash: -1.48% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: 0.4% Traditional ROI: -1.48%
Lot 5 Olmstead Dr Woodstock, IL Lot 5 Olmstead Dr, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$89,000	Airbnb cash on cash: 8.6% Traditional cash on cash: 2.6% Airbnb Rental Income: $1569 Traditional Rental Income: $596 Airbnb ROI: 8.6% Traditional ROI: 2.6%
7 Galaxy Way Woodstock, IL	N/A beds \| N/A baths \| N/A	$189,000	Airbnb cash on cash: 2.48% Traditional cash on cash: -0.47% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: 2.48% Traditional ROI: -0.47%
Lot 2 Olmstead Dr Woodstock, IL Lot 2 Olmstead Dr, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$89,000	Airbnb cash on cash: 8.6% Traditional cash on cash: 2.6% Airbnb Rental Income: $1569 Traditional Rental Income: $596 Airbnb ROI: 8.6% Traditional ROI: 2.6%
0 N Seminary Ave Woodstock, IL 0 N Seminary Ave, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$169,500	Airbnb cash on cash: 3.12% Traditional cash on cash: -0.15% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: 3.12% Traditional ROI: -0.15%
00 State Route 120 Woodstock, IL 00 State Route 120, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$200,000	Airbnb cash on cash: 2.18% Traditional cash on cash: -0.61% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: 2.18% Traditional ROI: -0.61%
9999 Calhoun St Woodstock, IL	N/A beds \| N/A baths \| N/A	$295,000	Airbnb cash on cash: 0.45% Traditional cash on cash: -1.45% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: 0.45% Traditional ROI: -1.45%
2384 Linden Dr Woodstock, IL 2384 Linden Dr, Woodstock, IL 60098 \| Townhouse	2 beds \| 2 baths \| 1,268 sq.ft.	$237,500	Airbnb cash on cash: 2.93% Traditional cash on cash: 2.89% Airbnb Rental Income: $2093 Traditional Rental Income: $1546 Airbnb ROI: 2.93% Traditional ROI: 2.89%
10625 Bull Valley (lot 157) Dr Woodstock, IL 10625 Bull Valley (lot 157) Dr, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$85,000	Airbnb cash on cash: 9.12% Traditional cash on cash: 3.93% Airbnb Rental Income: $1569 Traditional Rental Income: $686 Airbnb ROI: 9.12% Traditional ROI: 3.93%
327 Burbank Ave Woodstock, IL 327 Burbank Ave, Woodstock, IL 60098 \| Single Family Residential	3 beds \| 2 baths \| 1,080 sq.ft.	$195,000	Airbnb cash on cash: 6.61% Traditional cash on cash: 3.71% Airbnb Rental Income: $2525 Traditional Rental Income: $1378 Airbnb ROI: 6.61% Traditional ROI: 3.71%
330 Leah Ln #3B Woodstock, IL 330 Leah Ln #3B, Woodstock, IL 60098 \| Condo/Coop	1 beds \| 1 baths \| 661 sq.ft.	$134,999	Airbnb cash on cash: 2.88% Traditional cash on cash: 2.27% Airbnb Rental Income: $1580 Traditional Rental Income: $1048 Airbnb ROI: 2.88% Traditional ROI: 2.27%
524 Amsterdam St Woodstock, IL 524 Amsterdam St, Woodstock, IL 60098 \| Single Family Residential	2 beds \| 1 baths \| 672 sq.ft.	$199,900	Airbnb cash on cash: 4.48% Traditional cash on cash: 1.43% Airbnb Rental Income: $2093 Traditional Rental Income: $977 Airbnb ROI: 4.48% Traditional ROI: 1.43%
11012 Lucas Rd Woodstock, IL Welcome home to this spacious and beautifully maintained two-story retreat offering 4 bedr...	5 beds \| 3 baths \| 2,448 sq.ft.	$724,900	Airbnb cash on cash: 6.93% Traditional cash on cash: 2.75% Airbnb Rental Income: $7414 Traditional Rental Income: $3160 Airbnb ROI: 6.93% Traditional ROI: 2.75%
16512 Nelson Rd Woodstock, IL 16512 Nelson Rd, Woodstock, IL 60098 \| Single Family Residential	9 beds \| 5 baths \| 7,516 sq.ft.	$995,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 1.53% Airbnb Rental Income: $7414 Traditional Rental Income: $4529 Airbnb ROI: 3.11% Traditional ROI: 1.53%
0 IL Rt 47 Rte Woodstock, IL 0 IL Rt 47 Rte, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$310,000	Airbnb cash on cash: 0.28% Traditional cash on cash: -1.2% Airbnb Rental Income: $1569 Traditional Rental Income: $689 Airbnb ROI: 0.28% Traditional ROI: -1.2%
1417 Walnut Dr Woodstock, IL	3 beds \| 1 baths \| 1,000 sq.ft.	$259,900	Airbnb cash on cash: 4.39% Traditional cash on cash: 3.52% Airbnb Rental Income: $2525 Traditional Rental Income: $1702 Airbnb ROI: 4.39% Traditional ROI: 3.52%
2046 Deep Cut Rd Woodstock, IL 2046 Deep Cut Rd, Woodstock, IL 60098 \| Single Family Residential	2 beds \| 1 baths \| 1,392 sq.ft.	$400,000	Airbnb cash on cash: 0.65% Traditional cash on cash: -0.21% Airbnb Rental Income: $2093 Traditional Rental Income: $1231 Airbnb ROI: 0.65% Traditional ROI: -0.21%
207 Fremont St #3 Woodstock, IL 207 Fremont St #3, Woodstock, IL 60098 \| Condo/Coop	2 beds \| 1 baths \| 1,126 sq.ft.	$175,000	Airbnb cash on cash: 3.44% Traditional cash on cash: 1.31% Airbnb Rental Income: $2093 Traditional Rental Income: $1200 Airbnb ROI: 3.44% Traditional ROI: 1.31%
727 Elm Ln #308 Woodstock, IL 727 Elm Ln #308, Woodstock, IL 60098 \| Condo/Coop	2 beds \| 1 baths \| 836 sq.ft.	$139,900	Airbnb cash on cash: 5.65% Traditional cash on cash: 2.71% Airbnb Rental Income: $2093 Traditional Rental Income: $1161 Airbnb ROI: 5.65% Traditional ROI: 2.71%
824 Washington St Woodstock, IL 824 Washington St, Woodstock, IL 60098 \| Single Family Residential	3 beds \| 1 baths \| 1,506 sq.ft.	$310,000	Airbnb cash on cash: 3.01% Traditional cash on cash: 1.5% Airbnb Rental Income: $2525 Traditional Rental Income: $1475 Airbnb ROI: 3.01% Traditional ROI: 1.5%
10410 Saddlebred Trl Woodstock, IL 10410 Saddlebred Trl, Woodstock, IL 60098 \| Single Family Residential	5 beds \| 2 baths \| 2,564 sq.ft.	$499,000	Airbnb cash on cash: 9.39% Traditional cash on cash: 1.79% Airbnb Rental Income: $7414 Traditional Rental Income: $2445 Airbnb ROI: 9.39% Traditional ROI: 1.79%
1073 Castleshire Dr #1073 Woodstock, IL 1073 Castleshire Dr #1073, Woodstock, IL 60098 \| Condo/Coop	2 beds \| 1 baths \| 1,057 sq.ft.	$205,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 1.88% Airbnb Rental Income: $2093 Traditional Rental Income: $1260 Airbnb ROI: 3.4% Traditional ROI: 1.88%
412 Saint Johns Rd #A Woodstock, IL 412 Saint Johns Rd #A, Woodstock, IL 60098 \| Condo/Coop	2 beds \| 1 baths \| 1,100 sq.ft.	$155,000	Airbnb cash on cash: 5% Traditional cash on cash: 2.32% Airbnb Rental Income: $2093 Traditional Rental Income: $1157 Airbnb ROI: 5% Traditional ROI: 2.32%
809 Washington St Woodstock, IL 809 Washington St, Woodstock, IL 60098 \| Single Family Residential	3 beds \| 2 baths \| 1,125 sq.ft.	$269,900	Airbnb cash on cash: 3.92% Traditional cash on cash: 3.31% Airbnb Rental Income: $2525 Traditional Rental Income: $1761 Airbnb ROI: 3.92% Traditional ROI: 3.31%
262 Schryver Ave Woodstock, IL 262 Schryver Ave, Woodstock, IL 60098 \| Single Family Residential	3 beds \| N/A baths \| 1,144 sq.ft.	$265,000	Airbnb cash on cash: 4.05% Traditional cash on cash: 2.45% Airbnb Rental Income: $2525 Traditional Rental Income: $1515 Airbnb ROI: 4.05% Traditional ROI: 2.45%
422 Stewart Ave Woodstock, IL 422 Stewart Ave, Woodstock, IL 60098 \| Single Family Residential	3 beds \| 1 baths \| 1,586 sq.ft.	$299,900	Airbnb cash on cash: 3.22% Traditional cash on cash: 1.72% Airbnb Rental Income: $2525 Traditional Rental Income: $1494 Airbnb ROI: 3.22% Traditional ROI: 1.72%
902 Wicker St Woodstock, IL 902 Wicker St, Woodstock, IL 60098 \| Single Family Residential	3 beds \| 1 baths \| 1,593 sq.ft.	$325,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 1.26% Airbnb Rental Income: $2525 Traditional Rental Income: $1470 Airbnb ROI: 2.72% Traditional ROI: 1.26%
541 Leah Ln #2C Woodstock, IL 541 Leah Ln #2C, Woodstock, IL 60098 \| Condo/Coop	2 beds \| 2 baths \| 881 sq.ft.	$184,900	Airbnb cash on cash: 3.36% Traditional cash on cash: 3.03% Airbnb Rental Income: $2093 Traditional Rental Income: $1496 Airbnb ROI: 3.36% Traditional ROI: 3.03%
139 W Melody Ln Woodstock, IL 139 W Melody Ln, Woodstock, IL 60098 \| Single Family Residential	3 beds \| 1 baths \| 1,560 sq.ft.	$289,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 1.87% Airbnb Rental Income: $2525 Traditional Rental Income: $1485 Airbnb ROI: 3.45% Traditional ROI: 1.87%
1075 Castleshire Dr #1075 Woodstock, IL 1075 Castleshire Dr #1075, Woodstock, IL 60098 \| Condo/Coop	2 beds \| 1 baths \| 1,188 sq.ft.	$239,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 1.33% Airbnb Rental Income: $2093 Traditional Rental Income: $1329 Airbnb ROI: 2.33% Traditional ROI: 1.33%
213 Grove St Woodstock, IL 213 Grove St, Woodstock, IL 60098 \| Single Family Residential	3 beds \| 1 baths \| 1,363 sq.ft.	$215,000	Airbnb cash on cash: 5.71% Traditional cash on cash: 3.14% Airbnb Rental Income: $2525 Traditional Rental Income: $1391 Airbnb ROI: 5.71% Traditional ROI: 3.14%
867 Clay St Woodstock, IL 867 Clay St, Woodstock, IL 60098 \| Single Family Residential	3 beds \| 1 baths \| 1,776 sq.ft.	$274,900	Airbnb cash on cash: 3.79% Traditional cash on cash: 1.9% Airbnb Rental Income: $2525 Traditional Rental Income: $1424 Airbnb ROI: 3.79% Traditional ROI: 1.9%

Vacation Rentals in Woodstock

There are 49 vacation rental properties available for sale in the city of Woodstock . The median list price of Airbnb properties available for sale in Woodstock is $351,789 and the average price per square foot is $147. The cash on cash return on vacation rentals in Woodstock is 3.00%. The average monthly short term rental income in Woodstock is $2,525.

Woodstock, IL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 49 Airbnb properties available for sale in Woodstock.

In 2026, the best neighborhood to buy short term rental property is Woodstock.

In September 2026, the average Airbnb occupancy rate in Woodstock is 36%.

Airbnb data on vacation rentals in Woodstock, IL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Woodstock, IL market insights, guest information and booking details, seasonality trends and historical Woodstock, IL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Woodstock, IL

1109 Wicker St

Woodstock, IL

3 beds | 1 baths | 1,088 sq.ft.

$299,900

Airbnb cash on cash: 4.29%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $2525

Traditional Rental Income: $1682

Airbnb ROI: 4.29%

Traditional ROI: 3.46%

1019 N Madison St

Woodstock, IL

2 beds | 1 baths | 784 sq.ft.

$215,000

Airbnb cash on cash: 4.91%

Traditional cash on cash: 4.29%

Airbnb Rental Income: $2093

Traditional Rental Income: $1429

Airbnb ROI: 4.91%

Traditional ROI: 4.29%

110 N Seminary Ave

Woodstock, IL

3 beds | 1 baths | 1,125 sq.ft.

$224,900

Airbnb cash on cash: 5.72%

Traditional cash on cash: 4.38%

Airbnb Rental Income: $2525

Traditional Rental Income: $1630

Airbnb ROI: 5.72%

Traditional ROI: 4.38%

434 E Calhoun St

Woodstock, IL

3 beds | 1 baths | 810 sq.ft.

$220,000

Airbnb cash on cash: 6.48%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $2525

Traditional Rental Income: $1463

Airbnb ROI: 6.48%

Traditional ROI: 4.31%

708 S Rose Farm Rd

Woodstock, IL

5 beds | 4 baths | 4,084 sq.ft.

$1,995,000

Airbnb cash on cash: 1.62%

Traditional cash on cash: 0.93%

Airbnb Rental Income: $7414

Traditional Rental Income: $4706

Airbnb ROI: 1.62%

Traditional ROI: 0.93%

15309 Kishwaukee Valley Rd

Woodstock, IL

5 beds | 4 baths | 7,279 sq.ft.

$1,249,000

Airbnb cash on cash: 2.87%

Traditional cash on cash: 2.03%

Airbnb Rental Income: $7414

Traditional Rental Income: $5018

Airbnb ROI: 2.87%

Traditional ROI: 2.03%

8205 Austin Trl

Woodstock, IL

5 beds | 2 baths | 3,200 sq.ft.

$949,000

Airbnb cash on cash: 3.42%

Traditional cash on cash: 0.55%

Airbnb Rental Income: $7414

Traditional Rental Income: $3458

Airbnb ROI: 3.42%

Traditional ROI: 0.55%

0000 Lake Shore Dr

Woodstock, IL

N/A beds | N/A baths | N/A

$300,000

Airbnb cash on cash: 0.39%

Traditional cash on cash: -1.49%

Airbnb Rental Income: $1569

Traditional Rental Income: $589

Airbnb ROI: 0.39%