Vacation rentals in Twin Lakes

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Top-rated vacation rentals in Twin Lakes

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Condo in Kenosha

4.93 out of 5 average rating, 172 reviews

Inviting, spacious apt! Ideal for stay & work

This brand new basement apartment is an amazingly pleasant, spacious and private unit (over 950 sq. ft). Whatever the motive of your trip is —work from home, business, family function, wedding, graduation, friends, or simply a vacation escapade — you will enjoy the freedom this space provides. This residential, private neighborhood apartment is carefully designed. The full kitchen, classy bathroom, plush and extra-comfortable king size bed, the TV and all the amenities will fulfill your needs.

Sep. 14 – 21

$145 CAD per night

Guest favourite

Cabin in Twin Lakes

5.0 out of 5 average rating, 48 reviews

Secluded in the Woods, near lakes & trails-kitchen

Owl's Rest Cabin is nestled in acres of fully wooded, peaceful forest. You're a 4 min drive to Lake Mary & downtown Twin Lakes. This is a cozy couple's retreat or small family getaway with a fireplace, full kitchen, washer/dryer and you are only 15 min to Lake Geneva. Many activities nearby - festivals, downhill skiing, tubing, snow shoeing, hiking, boat rentals, golf, beach. Eco conscious cabin, including Level 2 electric vehicle charging & more. Please send me a message with any questions.

Sep. 1 – 8

$529 CAD per night

Guest favourite

Condo in Lake Geneva

4.98 out of 5 average rating, 174 reviews

Lake Geneva Cloud 9

A resort community with outdoor pool (open during the summer season only) boat launch, tennis courts and small craft rentals on the premises. Beautiful views of Lake Como from the patio. Five minute drive to Downtown Lake Geneva. Free parking and keypad entry. Walk to The Ridge Hotel Resort and enjoy the use of their amenities for a small user fee which includes indoor and outdoor pools, spa, whirlpool, fitness center and restaurant. The condo is comfy and ready to make your stay memorable.

Nov. 13 – 20

$266 CAD per night

Guest favourite

Home in Beach Park

4.98 out of 5 average rating, 161 reviews

B’s Farmhouse Cottage 2-bedroom duplex.

Experience the best of the midwest! Enjoy a newly remodeled "Magnolia Farm" inspired 2-bedroom duplex, all to yourself near everything you need. 50 Miles from Milwaukee, miles from Chicago, and 2 miles having your toes in the sand at Lake Michigan. We are minutes away from the Great Lakes Naval Station and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge. Whatever brings you here make J&B's Farmhouse Cottage your home away from home today.

Apr. 7 – 14

$214 CAD per night

Guest favourite

Home in Twin Lakes

5.0 out of 5 average rating, 13 reviews

Cozy Getaway by the Lake

Relax with the whole family at this peaceful getaway. Come take in the lake & all Twin Lakes has to offer. Offerings including open concept, family room in the basement for entertainment w/many games to play, two tvs 65” and 55”, 5 minute walk to the lake and Wild Child restaurant, 7 minute walk to Manny’s Snack Shack, 12 minute walk to Rumpoles Banquet Hall, golf course 1.3 miles away, great biking, Wilmot Mtn 10 minute drive, & nearby Lake Geneva & activities. Come visit home away from home!

May 5 – 12

$328 CAD per night

Guest favourite

Cabin in Spring Grove

4.9 out of 5 average rating, 20 reviews

Enjoy a Getaway @ The Lake-Heim by Chain-O-Lakes

Enjoy a comfy retreat in this cute 1BR home nestled right next to Grass Lake, IL. A lovely space to unwind and relax by the lake whether it is work or play. Awake refreshed to a quiet morning, ready for a day of water activities with impressive views. Early risers can catch a sunrise to die for. Indulge in the comfort and tranquility of this lakehouse cabin. We conduct regular pest treatment to keep pests away, but being close to nature and the lake, expect occasional bugs in warmer weather.

May 8 – 15

$181 CAD per night

Guest favourite

Home in Twin Lakes

5.0 out of 5 average rating, 20 reviews

Beautiful Twin Lakes home + lovely private setting

Lovely , peaceful rural homestead perfect for traveling workers …….or just to get away from it all. *NO OCCUPANCY TAXES ON 30+ DAY STAYS Home is completely remodeled & very nicely furnished. 4 smart TVs, fast Wi-Fi , YouTube TV, RO water, huge beautiful yard and home gym. **NIGHTLY RATE IS BASED ON OCCUPANCY** $20 pp for each additional person > 1. max 6 persons. No children under 6 yrs. Persons on property is limited to registered guests only unless specific agreement is made in advance.

Sep. 18 – 25

$243 CAD per night

Superhost

Home in Twin Lakes

4.93 out of 5 average rating, 134 reviews

Cove at 420: Modern Lake Front Home near Chicago

Welcome to the Cove at 420. A modern vacation paradise where indoor and outdoor lines blur. Every space is designed for enjoyment. A short 75 minute drive from Chicago, this is a true retreat. Wake up to beautiful sunrise views or enjoy them from a kayak on the water. We offer kayaks, paddle boards, hot tub & sauna, Sonos sound system, a fire pit and plenty of yard games for our guests. Hidden on a cul-de-sac between Lake Mary and Lake Elizabeth, enjoy the best of lake life!

Sep. 18 – 25

$854 CAD per night

Guest favourite

Guesthouse in McHenry

4.95 out of 5 average rating, 155 reviews

"The Apartment" in the heart of downtown McHenry

We welcome you to be our guest in this charming, historic home built in 1911 by a German mason. This upper unit Apartment is a spacious 1,100 square feet, lovingly restored with a vintage aesthetic in 2018. The private entrance to "The Apartment" will lead you to; 2 cozy bedrooms & 1 vintage inspired yet modern bath with walk in shower. A large living room, dining area and bright clean kitchen will make you feel right at home. 9 foot ceilings and tons of natural light through out.

Feb. 25 – Mar. 4

$202 CAD per night

Guest favourite

Home in Ingleside

4.93 out of 5 average rating, 110 reviews

Gorgeous Nautical 2/2 Lake House Chain O' Lakes

Unique and cute 2 bed / 2 bath nautical lake house has the best views of the Chain O' Lakes. Be amazed on the walk out lake view wood deck in the back yard, and watch sunsets fall over the bay and color the sky. The back patio is a great place to relax, entertain & relax. Fish or dock your watercraft at our pier if needed. There is an optional 5-6 person hot tub on the back deck for you to relax and unwind (See access and maintenance fee). Fully remodeled modern lake house

Oct. 10 – 17

$315 CAD per night

Guest favourite

Home in Lake Geneva

5.0 out of 5 average rating, 5 reviews

New Pet-Friendly Lake Geneva Escape

Escape to our pet-friendly retreat, perfect for friends and family getaways! With 2 bedrooms accommodating up to 6 guests, this cozy abode offers proximity to thrilling activities like zip lining and the serene Lake Geneva Beach, just a short 4-minute drive away. Bring along your furry friend to enjoy the spacious backyard and BBQ area. Equipped with everything you need for a weekend escape or a relaxing vacation, our property promises a memorable stay for all!

Feb. 26 – Mar. 5

$258 CAD per night

Guest favourite

Condo in Lake Geneva

4.93 out of 5 average rating, 425 reviews

Charming, Cozy & Quaint Condo in Lake Geneva!

Quaint 1 BD 1 BA Condo by Lake Como. The association outdoor pool is newly remodeled. There is a boat launch and parking, paddle board rentals, and tennis court. The hotel next door has pools to use for a fee. Dine at the popular nearby Mars restaurant or check out the Ridge Hotel’s coffee shop, restaurant & huge outdoor fire pit! Condo offers towels, toiletries, games, WiFi, basic cable, Roku, electric grill, gas fireplace, drip & K-cup coffee, tea, & water!

Sep. 23 – 30

$224 CAD per night