Family-friendly holiday rentals in Chaska

Country Retreat - relaxing, clean, pet friendly

This clean modern space features country charm, peace and quiet, and gorgeous scenery. It's off the main road, but close enough to everything. 35 minutes west of the MSP airport. The space is the entire lower level. Private entrance, heated floors and ice cold AC. Two smart T.V's, one in the bedroom and living room. Well-stocked kitchenette and nice refrigerator. Plenty of space to cook, watch TV, work, or just rest. a nice grill and campfire space is provided. Pets are welcome.

Happy Trails

WINTER, We have a circular driveway and a flat driveway. I do my own snow plowing. This is a lovely 640 square foot, mother in law apt on a 5 acres estate, It's very private, quiet and safe with a private entrance. The traffic is light and contact with people is non-existent. Four rooms with a Queen bedroom, A full size pull out sofa in the sitting room, a kitchenette with laundry facilities and a full bath with shower. We are 20 min from downtown Mpls. Off street parking.

Victorian 3rd Floor Studio

Welcome to our charming 3rd-floor studio located within a Victorian home in the heart of the NE Arts district! This cozy retreat boasts an abundance of natural light streaming in through skylights, illuminating a space adorned with beautiful plants, creating a serene and inviting ambiance. This delightful haven features a warm fireplace perfect for cozying up on chilly evenings. Please note, there is some low clearance near the head of the bed and in the bathroom/kitchen area.

Lakeview Retreat w/sauna & more

Lake retreat awaits you! Smores at the fire pit, kayak, SUP, paddleboat, fish on quiet lake (catch/release). Bike/Hike trails in Carver Park/Lowry Nature Cntr. Grill dogs/burgers right outside your private, ground level living space w/ queen bed, living room, kitchen, bath, & sauna. Trails down hill to lake - watch sunset. Complimentary use of water toys. Summer, Spring Fall - enjoy swim, canoe, kayak, fishing in our duck boat, hike, bike. Winter snowshoe, ski, bike, hike!

Charming Minneapolis Guest Suite

Welcome to The Irving! A charming and cozy suite located in the heart of the historic Lynnhurst neighborhood of Minneapolis, just south of Lake Harriet and the shores of Minnehaha Creek. This well appointed guest suite is just a 2 minute drive (or 15 minute walk) from some of Minneapolis’ most beloved restaurants and neighborhood haunts. A perfect place to stay while visiting beautiful Minneapolis for either business or pleasure. We look forward to welcoming you soon!

Cozy Lakefront Cottage

There are 2 bedrooms, 1 full bath, a spacious kitchen open to a great room that is perfect for socializing, cooking and relaxing, watching the ducks swim by. Dock installed in 2025. The lake is quiet, non motorized, perfect for canoeing/paddle boarding. Easy walk to the village and access to bike trails. 1 mile walk to Lake Minnetonka. Dogs require approval - please message about your dog. Interior is updated, exterior gives a rustic cottage feel. There is no dock.

Look no further | Private entrance

Entire 1500 sq ft private guest suite/walkout basement w/ private entry just a couple of miles from all that the Lake Minnetonka & Chanhassen area have to offer including Paisley Park. Includes a private bedroom with queen bed & a separate sleeping room with two twin beds (double blackout curtain - no door on room), private full bath, kitchenette, family room surround TV system, Foosball & pool table. Shared backyard oasis w/ patio, grille, hot tub & fire pit.

Minnetonka Carriage House Guest Suite

This is a separate guest suite built with excellence, comfort, and relaxation in mind. It has a separate entry inside the Carriage House. Owner works in and around the hospitality industry and has a goal to make your experience here a great one: great bed and sleep, great shower, great place to work and to relax. In a residential area but close to many great restaurants, retail shops, and services . This is designed for business travelers or couples.

Yellowstone feel 3Bd lodge/farm

This picturesque farm with a charming 3 bedroom cottage home will give you the best of what country living has to offer! The home has a true "Yellowstone" feel to it with its style and decor. Feel refreshed when you stay in this rustic gem. The home has one king bed in the primary suite and two queens in the other two bedrooms. There is also a fold out couch with a full-size mattress that is very cozy in front of the fireplace.

Cedar House Retreat

Amazing spacious property with Lake View! Gather your friends, or bring the whole family to this beautiful home. This retreat has a spacious open floor plan with two owner's suites, a home gym, a sauna for two, a home theater space, access to two lakes, one block from a public beach on Lake Minnewashta, and a park with a playground, tennis court, and pickle ball courts.

Private Space By Lots of Great Restaurants

Entire lower level flat with your own separate entrance and parking. My place is close to restaurants, Arboretum, Paisley Park, bike trails, and wineries. You’ll love my place because of the comfy bed and lots of space. My place is good for couples, solo adventurers, and business travelers. There is no cleaning fee.

Cozy clean comfort in a private winter setting

$100 per night in January 2026 and February 2026 HAPPY NEW YEAR! Completely Private lower level apartment with lush garden views from your very own patio. Ideal for relaxing as you visit family and friends or enjoy a quiet stay. Self check in through your own private entrance.