Pet-friendly holiday rentals in Chaska

Cozy Modern Bungalow. Dog Friendly. No Pet Fee!

You will be close to everything when you stay at this centrally-located home just steps away from the light rail making access to both downtowns a breeze. Walk to Allianz Field, Minnesota State Fair, Flannel Jax’s, Can Can Wonderland, and Turf Club. Take the light rail to Surley’s Brewery or MOA. There are many authentic restaurants and Grand Avenue shopping nearby. Bring your dog(s) and let them play in the privately fenced in backyard! Perfect for families visiting students at nearby colleges!

Luxury City 1 Bedroom King Suite

Step into a true urban retreat that has been fully renovated, offering 1,000 sq. feet of inspiring space. The modern European kitchen awaits your culinary adventures, while the serene living room, adorned with a large fireplace and 75" TV, invites relaxation. Flow seamlessly into the airy bedroom, featuring a king-size bed and a dedicated workspace. The bathroom, with its floor-to-ceiling tiles and luxurious rain shower, exudes elegance. For comfort, this unit, fully air-conditioned and heated.

Sibley Loft - adorable one bed one bath with patio

The Sibley Loft is a charming one bed one bath apartment on the second floor of our family home. The structure was built in 1921 and retains some of the original features. The space includes a living room, bathroom with a clawfoot tub, a small office area, kitchen and a patio. Guests have their own private entrance and street parking. We are located in the Standish neighborhood which is close to many restaurants, shopping and more. The airport is a 20 minute drive and MN center is 15 minutes.

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 the 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 are provided. Pets are welcome.

Carriage house with private garden

Art studio converted to guest house, powered mostly by solar panels, with vaulted ceilings, french doors to a private garden, full kitchen, office, bedroom, fold-out couch, washer/dryer, on large lot within walking distance of lake with beach and bike trails. Perfect spot for single person, couple or family. Privacy for working, writing, or enjoying the natural surroundings. Private garage and driveway. Patio dining with 6 chairs and grill. 40 foot lap pool shared with owner, by invitation

Tree Top Retreat

Minutes from the city conveniences; this quiet, private setting offers tree tops views with a rural feel. The Mississippi River and numerous hiking & biking trails are at your doorstep. This newly constructed apartment is within 15 minutes of CHS, Koch Refinery, Viking Lakes, and 20 minutes from MSP Airport & MOA. The apartment, which is above the garage of the main home, features private parking, entrance and deck. Climb the steps to the tree top views and enjoy all the amenities offered.

Very Spacious and Bright Home 15mins From Downtown

Escape to our 5,000 sq ft secluded forest home with private driveway access and ample privacy. Savor the stunning views from the many large windows and outdoor spaces, including a patio, screened porch, wrap-around deck, and tranquil koi pond. Stay productive with ultra-fast wi-fi and multiple workspaces. Indulge in luxury in the spacious main suite, featuring a jetted whirlpool tub and cozy gas fireplace. Conveniently located, it's just 15 minutes to downtown and 25 minutes to MOA & MSP.

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!

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.

Maple trails farm house

Fully furnished 4 Bedrooms with extra sofa beds for children, home with Bedding and Linens, Kitchen is equipped with Microwave, Refrigerator, Oven, Toaster, Coffee Maker, Dishwasher, Stove, Dishes and Silverware too. Large floor plan and over 4,500 sq.ft and has a terrific backyard oasis that includes a swimming pool ( open depending on weather permitting ) outdoor fireplace, a 3-season porch, perennial gardens and pond.Enjoy a calm stay with horses on property .

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.

Highland Guest House

The guest house is your private oasis in the heart of Highland Park, St. Paul. Complete with all the modern amenities to make your stay complete. This apartment is detached from the main house, and tucked behind the garage for ultimate privacy. Steps from the Mississippi River bluffs, and the restaurants of Highland Park. This private space includes a loft bedroom, kitchen, bathroom and living space. Just a 5 minute Uber Ride to the Light Rail or the airport.