Holiday rentals in Countryside Lake

The Fox Den / Midcentury A-frame

Our A-Frame is a mid-century gem with everything you envision in a cabin, plus all the comforts of home. It features a private dock with access to the Fox River and the Chain of Lakes, as well as direct entry to the Silver Creek Conservation Area. Located between the Fox River and the northern end of the Silver Creek Conservation Area, it’s only 1:15 from Chicago and 1:30 from Milwaukee. The ideal spot for a couple’s retreat, a small family adventure, or a solo escape to reconnect with nature.

Modern 4BR Lake Retreat • Walk to Beach & Main St

Lakeside Haven, a 4BR retreat on Bangs Lake. Steps from Main Street’s dining, shopping, and beaches, this modern home offers:
 🌊 Lake views & open living spaces 💻 High-speed Wi-Fi & workspace 🍳 Fully equipped kitchen & laundry 🚤 Nearby hiking, boat rentals, & events 🛏️ King & queen beds 🪟 Blackout screens Perfect for families, Navy graduations, and long stays. Enjoy the Triathlon, farmers market, cruise nights, ice fishing derby, and more. Dates fill quickly in every season. Book today!

Lovely apartment above Gelato Shop. Walk to shops

Enjoy a Cozy, warm place with lots of character! Centrally-located! Walk to Starbucks and eateries. Two story apartment with two entries. Sit on the front deck and enjoy a coffee. Get a pastry 2 doors down or across the street at Dunkin. Great restaurant 300 feet away. Many nice amenities including on site parking, two full bathrooms, large second floor bedroom for privacy. 23 minutes from Great Lakes Naval Base, 38 minutes to downtown Chicago, 22 minutes to Six Flags. Walk to commuter train.

Pet Friendly, Fenced In Yard, Lots to do Nearby!

Entire home included in your stay, big fenced in yard that is pet friendly! Updated, clean, 2 bedroom with 2 queen beds. 1 full bathroom. Laundry room with W/D. All hard surface flooring throughout (no carpet), kitchen has new appliances, dishwasher, coffee maker, toaster, microwave, fridge/freezer, quartz counters, all utensils stocked and available. There's a dining space with 4 chairs. Comfortable living room with couch and recliner, and wall mounted Smart TV. Patio, grill, outdoor space!

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

Walk to downtown McHenry. Heart of the Fox River

NO PETS Entire 2nd. floor. < 2 blocks away from downtown, Fox River Riverwalk. Pokémon Gym across the street. 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. Minutes from 2 State Parks, 1 with free boat/kayak launch. Several marinas, boat rentals, golf courses & other varieties of entertainment. Look at Bettye's Guidebook for more information.

TheGlassCabin @ HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

Beautiful 3 bdrm home, 20 min to Naval Base

Relax with the whole family at this peaceful place to stay. Quick 20min drive to Great Lakes Naval Base and 25mins to Great Wolf Lodge! This beautiful home is perfect for couples & families coming to Lake County to visit family or attend graduation from Great Lakes Naval Base. The renovated kitchen is well appointed, & in-unit laundry makes you feel right at home! All rooms have pillowy soft memory foam mattresses. You'll have access to the full home through a smartlock code.

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Lakeside Tiny House Farm Retreat

Nestled on 40 peaceful acres, this rare and unique tiny house retreat nested next to our private 5-acre pond invites you to slow down, breathe deeper, and reconnect with what matters most. Set on a no-till, regenerative flower farm, the land is alive with vibrant blooms, vegetable gardens, fruit trees, and chickens. Whether you’re seeking solitude, a romantic escape, or a soulful weekend reset, this is where time slows down and nature takes center stage.

124 Lofts #3 - Downtown Dundee - Walk to Dining

124 Lofts is a boutique collection of modern, design-forward lofts set within a beautifully restored historic building in downtown West Dundee. This listing is for Loft #3, a one-bedroom space featuring exposed brick, timber ceilings, and clean finishes that feel both character-driven and easy to enjoy. Each loft includes a king bed, private bath, kitchenette, fast Wi-Fi, and a 60" smart TV, just steps from restaurants, shops, and the Fox River.