Vacation rentals in Chaska

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Top-rated vacation rentals in Chaska

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Top guest favorite
A charming treehouse is nestled among the lush branches of a large, mature oak tree. The wooden structure features multiple levels with a spacious deck that connects to the main entrance, surrounded by greenery, creating a serene and natural environment.
Home in Cottage Grove
4.98 out of 5 average rating, 715 reviews

Tree House Luxury Stay

Perched high in the majestic arms of a 150 year old Burr White Oak tree. This cozy 1200 square foot, seven-room house not only has breathtaking views it also has enchanting and delightful surprises befitting of a fairytale. Climb 40 feet up onto the Observation Tower, where a telescope waits for you, ready to scan the night sky, and reveal the panorama of the heavens -- overlooking 500 acres of natural splendor right next door. Step into the hot, bubbling jets of the jacuzzi, or warm caress of the rain shower, and restore your spirits by soothing your muscles, melting away any residual tensions of the day. Get a restful sleep in one of our soft beds. In the morning, pad around on in-floor radiant heated floors (so cozy during winter-time.) Or enjoy your morning coffee on one of four outside decks. And don’t forget to solve the mystery of the Treehouse, that awaits your discovery within its wood beamed walls. This treehouse was custom designed by its architect with three dimensional chess in mind. Artisan architectural details are found throughout. Crystal chandeliers bedeck its high ceilings, and marble countertops grace the elegant, fully appointed kitchen. (A surround sound system helps set the mood for those special dinners in the dining nook.) One of two fireplaces adds luxurious touches to the primary bedroom with a queen bed, and hideaway bed in the secret room, along with a jacuzzi and rain shower in the primary bath, as well as a second bathroom in the secret room. Perfect for honeymooners, couples, business/corporate overnights, solo travelers and families with children over twelve years old. These are only a few of the many luxury details in this spectacular vacation spot must-see. Spend your days snuggled up beside the fireplace of your choice, while enjoying the panoramic views. You can stream your favorite movies and shows with Broadband Wi-Fi throughout the house. Come down for a leisurely walk around the grounds, and stop by to visit and feed the goats and chickens that call Hope Glen Farm their home in the corral of this historic farmstead. Bring your stress levels down and your heart rate up by walking over to Washington County Cottage Grove Park Reserve, just steps away, and answer its call to explore over 550 acres of fields and forests. Go hiking and biking down its trails, geocaching the hills and ravines for hidden treasures, or spend the afternoon fishing and kayaking in the lakes. And don’t let cooler temperatures keep you from discovering the pristine natural beauty of winter! Winter activities include cross country skiing and snowshoeing on the blankets of snow. Breathe deeply of the crisp Minnesota winter air -- truly one of life’s great pleasures. Plus, only a ten minute drive brings you to nearby Afton Alps in Afton State Park offering downhill skiing and snowboarding. For clarity, the Treehouse has 2 private bedrooms: Bedroom 1 is has a queen bed. Bedroom 2 has a bedroom with standard sofa bed with attached half bathroom, which is the secret room a must find. Give yourself the gift of this luxurious enchanting TreeHouse Suite in the treetops, for a enchanting vacation experience you'll never forget. Something to write home about!

Top guest favorite
A light-filled living area features a leather sectional sofa with purple accent pillows, complemented by a wooden dining set for four. Sunlight streams through multiple windows, highlighting wooden flooring and decorative artwork on the walls. A cozy reading chair and a floor lamp create a welcoming corner.
Cottage in Linden Hills
4.92 out of 5 average rating, 399 reviews

Charming Linden Hills cottage by Lake Harriet

Our enchanting 1+ BR, 2 level cottage backs up to prime Minneapolis William Berry Park and Lake Harriet. Fully-equipped kitchen plus breakfast nook, LR/DR, entry parlor w/piano, Br w/queen bed. Walk-out lower-level patio, family room w/sleeping cubby, queen-sized mattress, full-size laundry, Roku/internet, outdoor hot tub - glorious in winter! Just 800 feet from the shore of gorgeous Lake Harriet and a few blocks from Lake Bde Maka Ska (formerly Lake Calhoun), connected to all Minneapolis Lakes.

Guest favorite
A cozy living area is featured with a gray sectional sofa adorned with decorative pillows. Natural light enters through two black-framed windows, and a small potted plant is placed on a side table next to a floor lamp. A wooden coffee table adds a rustic touch.
Home in Wayzata
4.89 out of 5 average rating, 101 reviews

Gorgeous! Modern 3 Bed Home by Lake Mtka & Wayzata

Beautiful 3 bed 2 bath modern cottage. Clean, bright, cozy! Large yard, woods, privacy. In park next to house: winter sledding hill, ice skating, tennis courts, basketball, playground! 65” TV in living room, ceiling fans in bedrooms, all wood & tile floors. All beds are comfort memory foam! Large upper level master suite w/ king bed & luxury en-suite bath! Walk to Grays Bay on Lake Minnetonka, Libbs Lake Beach, parks, trails! 5-10 min to Wayzata—MN’s fave lakeside town! 15 min to Mpls!

Top guest favorite
A charming two-story farmhouse is set on a lush green landscape, surrounded by tall trees. The lawn is well-kept, providing a peaceful atmosphere. The clear sky above enhances the tranquility of the scene, while power lines add a subtle connection to the nearby road.
Guest suite in Prior Lake
4.93 out of 5 average rating, 296 reviews

Little Farm Getaway

Welcome to my little 8 acre oasis! Being the first farm I’ve ever lived on, I understand the peace and tranquility it can offer those who have never experienced it. Enjoy meeting my horses and mini donkeys, take a walk through my woods, or have a fire! Aside from being just far enough, but just close enough to all the happenings in the city, my newly remodeled private entry, ground level basement apartment offers an escape from the noise and a place to unwind and relax. NO CHORES REQUIRED! 😊

Top guest favorite
A charming two-story cottage with a dark green exterior is framed by a white picket fence. Large windows allow sunlight to illuminate the front porch, which features a welcoming green door. The landscaped yard includes a pathway lined with greenery.
Home in Linden Hills
4.99 out of 5 average rating, 158 reviews

Charming Boxwood Cottage in Linden Hills

Completely renovated cottage is just a 2 block stroll to downtown Linden Hills, 4 blocks to lakes. You will love the nearby restaurants, coffee shops, walking & biking paths, paddleboarding & kayaking or just stay home & enjoy the brand new kitchen, living rm w/ HDTV, gorgeous woodwork, 2 large upstairs bedrms, dedicated office, wifi, updated baths, laundry, 2 screened porches & private patio. 1 car garage. @boxwoodcottage on Insta. If booked, check out our nearby sister property: THE EWING.

Guest favorite
A comfortable living area features a large brown sectional sofa adorned with blue pillows, positioned near a wall of wood slices. An entertainment unit with a television is visible, alongside a retro arcade game and a pinball machine. A wooden coffee table rests on a textured area rug.
Guest suite in Watertown
4.87 out of 5 average rating, 128 reviews

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.

Top guest favorite
Cottage in Minnetonka
4.98 out of 5 average rating, 162 reviews

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

Top guest favorite
A spacious bedroom features large windows that bring in natural light and offer views of the surrounding trees. The room includes a cozy bed with decorative pillows and a modern gas fireplace situated nearby. Soft, neutral tones create a calming ambiance.
Home in Hopkins
4.95 out of 5 average rating, 149 reviews

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.

Guest favorite
A tranquil lakeside view is presented, featuring a dock with an American flag gently waving. Silhouetted trees frame the scene, while a soft sunset casts warm hues over the water. A solitary figure paddles peacefully in the distance, enhancing the serene atmosphere.
Home in Excelsior
4.91 out of 5 average rating, 219 reviews

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!

Top guest favorite
A cozy family room features two cushioned chairs with textured fabric, positioned around a central table. A fireplace with a white mantel is visible beneath a wall-mounted television. A woven basket and a portable lamp are included in the space, enhancing the room's ambiance.
Cottage in Excelsior
4.98 out of 5 average rating, 234 reviews

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.

Top guest favorite
Guest suite in Excelsior
4.82 out of 5 average rating, 173 reviews

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.

Top guest favorite
The rustic cottage features a wooden exterior with a sloped roof and a stone chimney. A welcoming porch is framed by lush greenery and a well-maintained lawn, enhancing the serene outdoor setting.
Farm stay in Mayer
4.97 out of 5 average rating, 147 reviews

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.

Popular amenities for Chaska vacation rentals

When is the best time to visit Chaska?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$28,870 GYDG$31,380 GYDG$35,983 GYDG$40,167 GYDG$42,886 GYDG$52,719 GYDG$48,117 GYDG$39,748 GYDG$42,886 GYDG$42,677 GYDG$40,376 GYDG$43,933 GYD
Avg. temp-9°C-6°C1°C8°C15°C21°C24°C22°C18°C10°C2°C-6°C

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Chaska?

    Chaska has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Chaska?

    Experience the best of Chaska with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Chaska?

    Four-legged friends are welcome in Chaska. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Chaska?

    Yes! Work meets play with ease at over 10 vacation rentals in Chaska featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Chaska have air conditioning?

    Absolutely! We offer over 60 house rentals with air conditioning in Chaska. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chaska have a kitchen?

    Absolutely! We offer over 60 house rentals with a kitchen in Chaska. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chaska have wifi?

    Absolutely! We offer over 60 house rentals with wifi in Chaska. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chaska have free parking?

    Absolutely! We offer over 60 house rentals with free parking in Chaska. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Chaska

  • Total vacation rentals

    Explore 70 vacation rentals in Chaska

  • Nightly prices starting at

    Chaska vacation rentals start at G$6,276 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,430 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Chaska vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chaska rentals

  • 4.9 Average rating

    Chaska stays are highly rated by guests—averaging 4.9 out of 5!

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