Holiday rentals in Crooked Lake

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Top-rated holiday rentals in Crooked Lake

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Top guest favourite
A spacious deck is illuminated by soft lighting, showcasing several lounge chairs and umbrellas. The wooden surface reflects a recent rain, creating a serene atmosphere. The surrounding trees gently frame the outdoor space, enhancing the tranquility of the lakeside setting.
Home in Pleasant Lake
4.95 out of 5 average rating, 101 reviews

Modern Lakeside • Deck + Beach

Is this the best lakehouse in Indiana? Features (rare) FOUR spacious bedrooms, a fully-stocked kitchen, massive lighted deck, screened porch, large beach, firepit area, lake toys (kayaks, SUP boards, and paddleboat), and attentive hosts! You will see why The Sanctuary on Golden Lake is the place to make lifelong memories with others. There's no rocky shoreline - enjoy floating or swimming without worrying about speedboats. NOTE: No pets. No parties. No smoking. No college-aged groups.

Top guest favourite
A charming lakefront house features a dark exterior with a welcoming red door. The manicured lawn leads from a gravel path to the entrance, with serene water visible beyond. Surrounding trees provide shade, enhancing the peaceful setting by Huyck Lake.
Home in Coldwater
4.92 out of 5 average rating, 142 reviews

Cozy Lakefront Cottage on Huyck Lake

Relax with the whole family at this peaceful, cozy place! 3 bedrooms 1 bath. Living room has a comfortable couch that pulls out into a bed along with additional seating. Full bath, kitchen, and laundry room are fully stocked for your comfort and enjoyment. Huyck Lake is a quiet, no wake lake. This house is perfect for a small to medium sized family or a romantic getaway. Master bedroom and guest bedroom have mounted TV’s. Family friendly. No to the following: pets, smoking, parties.

Top guest favourite
A serene view of Long Lake is presented, showcasing expansive waters under a clear blue sky. The surface of the lake reflects the sunlight, while lush greenery borders the landscape, offering a tranquil atmosphere conducive to relaxation.
Cottage in Pleasant Lake
4.97 out of 5 average rating, 147 reviews

Long Lake Cottage

Long Lake Cottage is on a 10 mph lake that is a pretty peaceful spot to relax. Enjoy bonfires, kayaking, fishing, and grilling at our place. Long Lake is a part of the Pigeon River chain that you can kayak along through multiple lakes. Less than 10 minutes from Angola (Trine University, Pokagon State Park, groceries, etc.). We hope you enjoy your stay! We have a strict cancellation policy, but we will refund you 100% of your stay if you do need to cancel 14 days before your arrival.

Top guest favourite
Guest suite in Angola
5 out of 5 average rating, 129 reviews

Cook’s Cottage: Luxury Lake Stay & Cooking Classes

Cook’s Cottage is a beautifully renovated lakefront retreat on Lake James, thoughtfully designed for guests who value calm, comfort, and time together. Enjoy sunset views, a sandy swim area, and a well-appointed chef’s kitchen. Enhance your stay with optional private, chef-led culinary experiences with owner Michelle, or—during summer—a relaxing historical boat tour with owner Corey. Whether celebrating an anniversary or simply slowing down, this is a stay meant to be savored.

Guest favourite
A clean and inviting living area features a plush dark-colored sofa with decorative pillows. Two comfortable armchairs frame a small side table and a lamp, while a patterned area rug adds warmth to the space. Soft, sheer curtains allow natural light to filter in.
Home in Angola
4.93 out of 5 average rating, 205 reviews

Home away from home

Relax with the whole family at this peaceful place to stay. This two bedroom home is very clean and peaceful with a nice outdoor patio and spacious living area. This has been completely remodeled with brand new furnishing. We are equipped for any quick last minute stays, but it’s also prepared for any long term stay needs as well. This is less than one mile from the city mound. It’s located on and bike trail that leads you to the beautiful Pokagon State Park.

Top guest favourite
The exterior of a lakefront double-wide house is shown, featuring a spacious sun porch with large windows that allow for ample natural light. A lush green lawn is visible in front, complemented by surrounding trees. A pathway leads to the entrance of the home.
Home in Coldwater
4.93 out of 5 average rating, 125 reviews

Jake's Lake Place w/pontoon rental

Jake's Place is on a private beautiful all sports lake (all DNR regulations apply) This is the perfect spot for your next family getaway. Spring feed lake, very clean and sandy bottom. This property has access to a second empty lot for additional yard. Multiple indoor and outdoor games, paddle boat, 4 kayaks and bond fire pit for relaxing after a great day on/in the lake. Jake's place faces the west for Gorgeous sunset viewing to end your day.

Top guest favourite
A charming log cabin features a welcoming facade with large windows framed by wooden accents. The entrance is accessed via a stone pathway lined with landscaped garden beds, showcasing lush greenery and colorful plants. Surrounding trees provide a serene, natural setting.
Cabin in Middlebury
4.99 out of 5 average rating, 405 reviews

Cabin off 39 - Peaceful, private one bedroom cabin

Kick back and relax in this calm, stylish space. Nestled among the trees, it provides a quiet getaway from the chaos of life allowing you to recharge and renew. The main residence is approximately 400 feet from the cabin. The cabin is secluded and yet close to local attractions, restaurants, biking and nature trails. The Cabin has a total of 420 sq ft living space with 280 sq ft on the ground floor and a 140 sq ft bedroom loft.

Guest favourite
A waterfront cabin is depicted with a large glass front, allowing ample natural light inside. Lush green grass surrounds the house, complemented by tall trees. A pathway leads to a spacious deck area with outdoor seating and a grill, enhancing outdoor relaxation opportunities.
Home in Coldwater
4.84 out of 5 average rating, 113 reviews

Coldwater Lake Waterfront Cabin - Boat for Rent

Relax with the whole family at this peaceful waterfront lakehouse, with walk-in, sandy beach lake access. Boat available to rent, and space available for your boats. Spacious yard with plenty of parking. Coldwater Lake is over 1,600 acres of all-sports fun on desirable South Chain of Lakes in Coldwater, MI. The chain is 17 miles, traversable via pontoon or speedboat! The Cabin includes 3 bedrooms and 2.5 baths.

Guest favourite
A hot tub is positioned on a wooden deck, overlooking a serene lake at dusk. String lights are draped above, casting a warm glow. Reflections of trees and a dock are visible on the calm water's surface, enhancing the tranquil atmosphere.
Home in Bronson
4.97 out of 5 average rating, 325 reviews

Water’s Edge-Lakefront-Hot Tub-Kayaks-Pet Friendly

Tranquil lake living! The Water’s Edge is a great way to enjoy the lake. It is right on the water with kayaks, stand up paddle boards, and a canoe to venture out with. The hot tub accommodates 6 people. The sunroom has beautiful views as well as a couple of beds that can be used if the weather is nice. There is nothing better than falling asleep to lake sounds and a pleasant breeze! Please no college partyers.

Top guest favourite
The exterior of a two-story home is shown, featuring a landscaped backyard with greenery and garden plants. A multi-level deck is visible, along with patio furniture and an umbrella for shade. The surrounding trees provide a natural backdrop to the home.
Home in Angola
4.92 out of 5 average rating, 121 reviews

The Valor House on Crooked Lake

2,300 sq. foot, open concept, single family home with 50 feet of lakefront and lots of entertaining space. Located on the third basin of Crooked Lake. Multi-level deck space and large yard great for entertaining. Sand bar off the dock makes for a great swimming area. Wifi, large screen projector/cable TV/DVD/Netflix downstairs. Cable TV/DVD in all bedrooms.

Guest favourite
A modern shipping container home is set amidst a wooded landscape. The structure features large glass windows and a welcoming entryway. A daybed swing is visible on the porch, surrounded by lush green grass and tall trees, creating an inviting outdoor space.
Shipping container in Columbia City
4.94 out of 5 average rating, 199 reviews

The Steel Oasis-Container Home w/ Hot Tub!

Welcome to our modern shipping container home, tucked away in a 3 acre section of woods. This 40 foot high cube has been transformed into the perfect place to allow you to relax and escape reality. This Oasis includes everything from a porch swing daybed, hot tub, fire pit, and dual sided fireplace. The details are unmatched.

Guest favourite
An open living space features a comfortable sofa with a patterned throw, a coffee table, and accent chairs. The dining area showcases seating for four at a round table. Natural light is complemented by light-colored furnishings and a neutral color palette.
Home in Angola
4.93 out of 5 average rating, 30 reviews

Paradise Landing 3.0

Spend your days on the lake boating, swimming, or fishing. After a day on the water spend your evenings playing yard games in shaded lot or relaxing with the sunset views from the patio. Bring some firewood for the fire pit located on the property or walk over to Club Paradise for karaoke night and amazing food and drinks.

Popular amenities for Crooked Lake holiday rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. Steuben County
  5. Crooked Lake