Apartment vacation rentals in Woodstock

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Top-rated apartment rentals in Woodstock

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Top guest favorite

Apartment in Rockford

4.95 out of 5 average rating, 132 reviews

Hip-N-Colorful Prospect Smoke Free

Excited to offer this space to travelers! We have fun with some color. Queen bed in the first bedroom, XL twin beds in the back bedroom. Great location! Close to stylish, revitalized downtown Rockford with terrific restaurants, night life, shops, and galleries. Upper unit in vintage 4 family with long term tenants below and I live in the other upper. Absolutely no parties. Only registered guests. No smoking inside or outside on the property. Violation results in $500 cleaning fee/poor review

Top guest favorite

Apartment in McHenry

5 out of 5 average rating, 142 reviews

Walk to downtown McHenry. Heart of the Fox River

NO PETS Entire 2nd. floor. 1 block away from downtown, Fox River Riverwalk & Pokémon Gym. Full stocked kitchen, books, games, toys & extra amenities to make your stay beyond relaxing. 4:20 allowed in backyard & not in view of under the age of 21. Private smoking area in front too. Minutes away from 2 State Parks, 1 with free boat/kayak launch. Several marinas, boat rental, golf courses & huge variety of entertainment. Look at Bettye's Guidebook for more information & nearby entertainment.

Guest favorite

Apartment in Crystal Lake

4.96 out of 5 average rating, 125 reviews

Farmhouse Chic Home with a view. Downtown

Charming Historic Apartment in Downtown Crystal Lake Spacious second-floor apartment overlooking Downtown Crystal Lake, located in a vintage 1875 farmhouse. Steps away from over 100 restaurants, shops, coffee spots, and bars, all within a 2-minute walk. Enjoy updated bedding, modern comforts, and vintage finishes in a quiet space with no shared walls or upstairs neighbors. One parking space included, with additional lot park CHECKOUT OUR OTHER PROPERTIES HERE: www.airbnb.com/p/breganproperties

Superhost

Apartment in Highland Park

4.83 out of 5 average rating, 131 reviews

Chic Studio in Downtown Highland Park - By Metra

Discover our elegant studio unit in Highland Park, now featuring FREE parking! This simple yet comfortable space is perfect for couples, concert-goers, and small families. You'll find all the essential amenities you need, including a fully stocked kitchen, laundry facilities, and reliable Wi-Fi. Our location is ideal for exploring downtown Highland Park, with convenient access to top attractions, restaurants, and shops. Book now and discover your perfect home away from home on the North Shore.

Top guest favorite

Apartment in Lake Geneva

4.98 out of 5 average rating, 978 reviews

Geneva Street Inn in Maple Park Historic District

Geneva Street Inn is located one block away from the heart of Lake Geneva. This beautiful 1890's home is appealing to everybody whether your stay is a business trip, family, or even a couples getaway. A huge backyard and a front porch that will make you never want to leave. We strive to make your stay your "home away from home" with unique decor and it's timeless charm! Our price is inclusive cleaning fees (unless extenuating circumstances warrants a fee). We meet our guests at check-in.

Top guest favorite

Apartment in Aurora

4.99 out of 5 average rating, 182 reviews

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Guest favorite

Apartment in Algonquin

4.8 out of 5 average rating, 129 reviews

Waterfront Stay w/ Walk to Downtown Entertainment

Apartment overlooking the Fox River. Walking distance to downtown Algonquin. Free wifi & cable TV. Don't impose on family or friends, or settle for the bland experience of a box hotel. Instead, book a comfortable stay with great amenities and enjoy the river and downtown entertainment. You'll be able to relax, get a restful sleep, and enjoy your visit. You'll also notice the little touches and the extra effort made to assure you have an awesome stay. Private Bathroom and Kitchen.

Superhost

Apartment in Near North Side

4.82 out of 5 average rating, 796 reviews

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Guest favorite

Apartment in Rockford

4.93 out of 5 average rating, 570 reviews

Upscale Urban Retreat 1 bedroom, ground Floor

Charming and beautiful ground floor; wood floors and original woodwork. Secure keypad entry. Owner on adjoining premises. Minutes to Indoor Sports Factory, downtown nightlife, restaurants, shops, Japanese Gardens, Rockford Art Museum, Nicholas Conservatory and Sinnissippi Gardens.. 5 blocks to river and rec path. Centrally located quiet Edgewater Neighborhood District. Ideal for business travelers, couples, solo adventurers and more. High speed internet.

Superhost

Apartment in Elgin

4.8 out of 5 average rating, 177 reviews

Sherwood House

Enjoy the ambience of the Sherwood House, an 1884 Victorian built for Judge David Sherwood. Use of entire first floor apartment including a full kitchen is perfect for longer term stays. Original features include multiple stained glass windows, beautiful wood work, multiple decorative fireplaces and hardwood floors. Located just blocks from downtown Elgin, walk to shops, restaurants, the casino, bike trail or Metra. WiFi and off street parking.

Guest favorite

Apartment in Winthrop Harbor

4.94 out of 5 average rating, 310 reviews

warm, cozy, spacious, comfortable; special.

Large, Cozy, suite w sweet kitchenette for “portable” meals; full-size refrigerator/ freezer; a writing desk for work. Many little ( in case you forgot) items to keep you comfy. This is a quiet town on the gorgeous Lake Michigan. Near: 6 Flags, Great Lakes Navy Base; Cancer Treatment Centers of America & the city Chicago via the Metra in town. Convenient & Quiet. I have 3 dogs. They are kind, outgoing and will want to meet you.

Top guest favorite

Apartment in Palatine

4.97 out of 5 average rating, 177 reviews

Huge Sofa-King Bed-Easy Parking-Private Deck-Retro

MId Century Modern 1 Bedroom With Private Entrance in Downtown Palatine! Over 170 5 Star Reviews ★★★★★ "This place is amazing. It is so cute and cozy. The location is amazing, walking distance to everything downtown Palatine has to offer.." Abbey - February 2025 700sf Retro Apartment with a King Bed & Private Outdoor Space. Safe Off Street Parking. Just Steps to Public Transportation, Bars, Restaurants & More.