Places to stay in Woodstock

4.96 out of 5 average rating, 340 reviews

A lush garden pathway winds through vibrant flower beds and greenery, leading to a cozy seating area nestled under a tree. The stone path is framed by various plants, showcasing a tranquil outdoor setting perfect for relaxation.

Guest suite in West Town

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

Bungalow in Belmont Cragin

4.9 out of 5 average rating, 30 reviews

Located on Beautiful and Quite Boulevard!

Welcome to The Boulevard A spacious house recently updated located at the beginning of the beautiful quite boulevard. The house is on beautiful Wrightwood Neighborhood Greenway! This house is centrally located 5 minutes away from Metra train station ( Healy Station) that will get you downtown in 15 minutes. Check with Metra for train times. Drive Downtown in 20 minutes(no traffic), O'Hare airport, West Loop. 20 mins to Lakeview, Wrigleyville, Boystown, Logan Square, Bucktown & Wicker Park.

4.97 out of 5 average rating, 145 reviews

A serene pathway lined with lush greenery features tall trees and blooming flowers. An inviting red chair is positioned in the background. A friendly sign indicating 'KEEP RIGHT' guides guests along the landscaped route toward the cottages.

Bungalow in Lake Geneva

Private Cozy Cottage Lake Geneva, WI

Come stay at our top rated Bed & Breakfast, located two blocks from the beautiful Lake Geneva. Relax in our California king suites, each contains a spa tub and shower, with heated floors and towel rails in the bathroom. Your complimentary breakfast basket is placed in your fridge prior to arrival, as well as complimentary gift of wine & cheese. Free WIFI is available on the property. No Pets, ADULTS over 21 ONLY. *NOTE all guests are required to pay a 8% Lake Geneva Bed Tax at check in.

4.96 out of 5 average rating, 25 reviews

A staircase is shown leading downwards, lined with wooden walls and illuminated by overhead lights. A mat with the word 'WELCOME' sits at the bottom, while the floor features a contrasting black and white checkerboard pattern.

Apartment in Kenosha

Captain’s Quarters Kenosha Wi

This special place is close to everything, making it easy to plan your visit. Located in the heart of downtown Kenosha within Kenosha’s lakefront district. Walking distance to Captain Mike’s (best burger of Kenosha) and so many great local bars and restaurants, as well as area museums and art galleries. A 10 min stroll to the nearby beaches, marina and weekend farmers markets. Perfect for foodies, anglers, business needs, families and more. Private Chef available upon request. The

5 out of 5 average rating, 20 reviews

A modern kitchen area is characterized by sleek white cabinetry and stainless steel appliances. A white countertop hosts a small sink and stylish seating for two at the breakfast bar. A plant adds greenery, while natural light pours in through large windows.

Apartment in Bridgeport

CitySlickers/FreeParking/Laundry/FastWiFi!

-600 sq.ft apartment / 1st floor / -Free parking pad in rear / free street parking -Commute to Downtown: 15min (drive) / 28min (transit/train) / 22min(bike) -Walk score 93! Bike Score 92! Near Trains to Downtown!! -Gated access w/ Building video and security alarm system and noise monitoring equipment. -Kitchen is stocked w/ cookware, utensils, etc. -Washer and Dryer and Dishwasher in unit (free) -Rideshare(Uber/Lyft) / Bikeshares(Divvy) are bountiful -Safe, working class neighborhood

5 out of 5 average rating, 5 reviews

The dining area features a light blue wall, a wooden dining table set with decorative plates, and a centerpiece vase filled with flowers. Overhead, a ceiling fan offers a cooling breeze. Sliding glass doors open to an outdoor patio area with additional seating.

Home in Elmhurst

27min2City-Cozy~SLP10-15~Large patio w/dining~BBQ

Your family will be close to everything when you stay at this cenHit❤️N Save O'hare Airport - 7.2miles DWTN Chicago -17miles Outlet Mall/Bar/Restaurants/Entertainment District/Casino Shopping, Trains, City Center, Fast Food, Gyms, Parks, Golf and other recreational activities. (1-5mile) Easy access to Highway Free Dedicated Parking Space -2 Limit Street and Guest Parking ($$) 346mpg Speed, Dedicated Wifi 4K HDTV w Roku/Streaming -4rooms Fully Equipped + Stocked Kitchen w Coffee & Tea

4.94 out of 5 average rating, 36 reviews

The kitchen area features modern appliances and dark cabinetry, providing ample storage space. A granite countertop with bar seating overlooks the dining area, where a wooden table is set against a stylish wall. Soft lighting enhances the inviting ambiance of the combined living and kitchen space.

Home in Chicago

Floresitas Oasis, your home in Chicago

Welcome to Floresitas Oasis! A place where you and your guests can relax in the comfort of your own home! You will be close to the best restaurants, night scene, and near all of what Chicago and Pilsen has to offer when you stay at this centrally-located place. ***IMPORTANT NOTE*** When booking, please list the total number of guests that will be staying during your time with us. Any additional guests not originally in the inquiry will be charged an extra $100 per guest, per day.

4.85 out of 5 average rating, 68 reviews

A cozy living room features four plush purple chairs arranged around a circular table. A modern television is mounted above a white brick fireplace, complemented by bookshelves filled with various items. A large potted plant adds a touch of greenery, enhancing the warm atmosphere.

Home in Austin

A Comfortable Stay While You are Away in Oak Park

Welcome to this Oak Park home, conveniently minutes from the main expressway, train station, downtown Chicago, and the Medical Center. This entire Oak Park house is ideal for travelers seeking a tranquil and welcoming space to unwind in after a long day, medical professionals, visiting patients at the Medical Center, and families needing long-term housing. The residence is minutes from downtown Oak Park and the historical landmarks of Frank Lloyd Wright's home and studio.

Apartment in Logan Square

A modern kitchen and dining area features an expansive island with seating for four and an elegant dining table surrounded by stylish chairs. Four skylights allow natural light to fill the space, highlighting the blue walls and contemporary decor.

4.92 out of 5 average rating, 12 reviews

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: - Uber-fast Wifi streaming, - Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches - European decor - 2 kitchens - The popular 606 Trail access is 100 ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

4.92 out of 5 average rating, 26 reviews

A modern kitchen is presented with sleek white cabinetry and contrasting black hardware. The marble countertops are accentuated by under-cabinet lighting, highlighting a spacious layout. Stainless steel appliances integrate seamlessly, while a coffee maker and various kitchen utensils are arranged for convenience.

Townhouse in Elgin

Fully Renovated and Updated Home

Escape to this inviting 3-bedroom townhome, your perfect Elgin retreat. Unwind in style with two plush queen beds and a comfortable full bed, ensuring restful nights. Two modern bathrooms offer convenience and privacy. Electric vehicle owners will appreciate the dedicated charger. Explore the vibrant city of Chicago, just a 45-minute drive away. With Route 90 just 5 minutes away, you're well-connected to explore the area.

4.85 out of 5 average rating, 289 reviews

The exterior view showcases a well-maintained brownstone building with intricate architectural details. Steps lead up to a decorative entrance framed by a tree with fresh green leaves, enhancing the welcoming appearance of the home.

Guest suite in Chicago

Comfy/Private Entry & Bath/Free Parking - Win Win!

A Hidden GEM on a private block in Bronzeville, ranked one of the hottest neighborhoods in Chicago. Great for those looking to travel the city from Downtown (4 miles), to the lake (1 mile) to Hyde Park (walking distance) or those simply looking to stay in and rest in a peaceful place. Welcoming guests from near and far in this comfy studio designed specifically to host those for a great Chicago experience!

4.91 out of 5 average rating, 11 reviews

A well-lit staircase features polished wooden steps and railings. Natural light filters through a large window, illuminating the space. The walls are painted white, providing a clean and airy feel, while the detailing of the wooden banister adds a touch of elegance.

Home in Waukegan

Prairie Place

Enjoy a stylish experience at this lovely, centrally-located home. Perfect for graduations, family reunions, weekend getaways, or any other time you need a peaceful getaway. Close to the Naval base (10-15 min drive), Genesee Theater (walking distance), Lake Michigan (3 min drive), Gurnee/Great America (10-15 min drive) and more. Centrally located between Chicago and Milwaukee.

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Popular amenities for Woodstock places to stay

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Woodstock's top sights

Ethereal Confections8 locals recommend

Woodstock Opera House7 locals recommend

D.C. Cobb's4 locals recommend

Woodstock Theatre17 locals recommend

ALDI7 locals recommend

Woodstock station32 locals recommend

Other great vacation rentals in Woodstock

4.88 out of 5 average rating, 128 reviews

A spacious outdoor deck is depicted, featuring a small seating area with two wicker chairs and a matching table. A grill is positioned to one side, with large glass doors leading into the house. Lush greenery is visible in the background.

Home in Fox Lake

Lakefront Paradise

4.92 out of 5 average rating, 272 reviews

Home in Kenosha

Where Family & Friends Gather to Create & Remember

Apartment in Jefferson Park

A modern kitchen is equipped with sleek stainless steel appliances, including a microwave and dishwasher. Light countertops complement dark cabinetry, while a small countertop with two barstools provides a casual dining option. Natural light filters in through a window near the door.

4.64 out of 5 average rating, 28 reviews

City Gem: Stylish 3BR for Urban Explorers

4.92 out of 5 average rating, 348 reviews

Cabin in Trevor

Living the Lakehouse Dream

4.86 out of 5 average rating, 65 reviews

A charming two-story house is set within a lush green lawn, featuring large trees that provide shade. The front porch is approachable and includes a railing, while an American flag gently waves. A fence encloses the backyard, creating a private outdoor space.

Home in Twin Lakes

beach access, pet friendly yard, hot tub, 5 bedrms

4.96 out of 5 average rating, 81 reviews

Home in Lake Geneva

Sleeps 12, 5 bedroom, 2 living rooms and game room

4.92 out of 5 average rating, 26 reviews

A serene landscape is visible, showcasing a calm body of water surrounded by lush greenery. Tall trees frame the scene, with a clear blue sky filled with soft clouds overhead, creating a peaceful natural setting.

Home in Salem

Hideaway at the Ponderosa- 3bd 1Ba Country Cottage