Holiday rentals in Cortland

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Top-rated holiday rentals in Cortland

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

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Guest favourite

Home in Twin Lakes

4.86 out of 5 average rating, 65 reviews

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

4,000 sq ft 5 bedroom, 3.5 bath home. Short walk to Musial beach on Lake Elizabeth. Perfect for large families with multiple living areas. Island Kitchen with fireplace & den. 3 season room. Master bedrm with walkin shower. Large 2nd floor family room with lg tv, vinyl records and shuffle board! Outdoor grill & fire pit & free firewood. Close to Grand Geneva Resort, Lake Geneva and Wilmot Mtn. Boat dock available on Lake Elizabeth. Turnkey boat rental available. Short walk to Roadhouse bar.

Top guest favourite

Home in Freeport

4.98 out of 5 average rating, 176 reviews

Willow Lake Getaway Cozy for 2 - or large families

Beautiful 4 bedroom private lakefront home, cozy enough for 2, large enough for family gatherings for holiday/wk end escape/vacations. Hot tub for cool eves October-April. Extensive private decks with BBQ, outdoor dining & circular daybed with umbrella. 2 docks, 2 SUP boards, paddle boat, 2 kayaks, pingpong table, books and board games. 2 Master Suites with smart tv with private balcony & seating area. fire pit located next to 1st dock. Couples get a 10% discount, message me for details.

Guest favourite

Home in Rockford

4.93 out of 5 average rating, 45 reviews

Beautifully home with 5 bedrooms

Experience the ultimate vacation in this newly renovated 5-bedroom and 2-bath rental, perfect for families or groups of friends. Enjoy 4 king & 2 twin beds, a LUX eat-in kitchen, private yard, and a screened porch. This rental also offers on-site laundry and a 2-car garage attached to the property. Plus, pets are allowed so you don't have to leave your furry friends behind! Book your stay today and experience the ultimate getaway at this luxurious and well-appointed short term rental.

Top guest favourite

Home in Winthrop Harbor

4.94 out of 5 average rating, 16 reviews

The Harbor House - Amazing!

The Harbor House is simply AMAZING! Set on over an acre, this private beautiful home is perfect for making beautiful family and group memories. The spacious interior features a great room as well as a separate family room. The expansive kitchen is fully equipped. Smart TV's in all BR's, the GR and FR. Full size washer and dryer. This home boasts an expansive private yard featuring plenty of outdoor seating with a gas grill and firepit. Ample parking. RV parking (50 amp).

Top guest favourite

Home in Avondale

5 out of 5 average rating, 11 reviews

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

Guest favourite

Home in Twin Lakes

5 out of 5 average rating, 5 reviews

Rustic Cottage Downtown Twin Lakes

Embrace the allure of the lake in our cozy rustic retreat nestled directly across the street from Lake Mary in the heart of Twin Lakes. This wonderful cottage provides a unique blend of rustic charm and modern comfort, featuring a warm, woodsy interior, lots of natural light and gas fire pit for enjoying warm breezes and westward facing sunsets. This cabin is the perfect getaway for those seeking to reconnect with water and find solace in the beauty of Wisconsin lake life.

Superhost

Flat in Logan Square

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!

Guest favourite

Home in Cherry Valley

4.9 out of 5 average rating, 40 reviews

Riverside Log Cabin: King B+Hot Tub+Sauna

Welcome to your perfect getaway! Our house is ideal for couples, families, or small groups looking to escape the hustle and bustle of daily life and reconnect with nature. ★ Relax in Hot Tub ★ Rest in Sauna ★ Sleep - 3 Bedrooms, 5 beds ★ Gather around fire pit with family and friends ★ Rest peacefully in a 3 king-size beds ★ Watch your favorite shows on 4 Roku TV’s around house ★ Stay connected with fast Wi-Fi. ★ Play foosball tournaments ★ Hiking, fishing, kayaking.

Guest favourite

Cabin in North Utica

5 out of 5 average rating, 23 reviews

Luxurious Cabin / King Suite / Starved Rock!

Gorgeous 3 bed, 4 bath cabin perfect for an executive / corporate rental. This cabin sleeps 12 (and up to 18 with 3 additional sleeper sofas) and is fully furnished and stocked for you to move right in. End unit on the lake with beautiful water views. All bedrooms have brand new 50 in smart TVs and family room has large 65 in TV for great movie nights. High speed internet and cable TV throughout. Enjoy beautiful Starved Rock and Matthiessen State Park. EXTENDED STAY

Superhost

Home in Fox Lake

4.87 out of 5 average rating, 124 reviews

Lakefront Paradise

Relax and have fun with the family and friends at this unique getaway! We are situated directly on the lakefront with private access to our pier where you can enjoy world class sunset views. Jump in and go swimming, roast s'mores over a campfire right next to the water, grill up some burgers on the spacious deck or get some rest in our luxurious suites in this newly renovated (June 2021) home.

Superhost

Home in Round Lake Beach

4.85 out of 5 average rating, 73 reviews

Lake/Beach Getaway (Remodeled)

Have fun with the whole family at this stylish home. Everything has been recently renovated. This is directly across from a beach, which is perfect for winter and summer activities. We supply 2 kayaks, fishing poles (Bring your fishing boat)This place has 3 bedrooms, and a total of 5 beds. There is also a lot of dining and shopping, nearby. This is a hidden gem and brand new to AirBnb.

Superhost

Cottage in Antioch

4.83 out of 5 average rating, 169 reviews

#1 The Lodge @ The Cottages on Petite Lake

This beautiful and spacious lakefront lodge has views, charm and wonderful amenities including a private hot tub with lake views. Enjoy your morning coffee with a beautiful sunrise from your private deck right over the water with a private hot tub. Spend your days on the lake with the beach just steps away. End the night with a bonfire or movie in the comfortable great room.