A calm river with a bridge, surrounded by autumn-colored trees and a dock with boats.

Hotels with Swimming Pools in Lakeside

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Lakeside Hotels with Swimming Pools

Tonight
8 Oct - 9 Oct
Tomorrow
9 Oct - 10 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Lakeside hotels with a pool

A hotel with a swimming pool, outdoor seating, and a large building with multiple windows.
An outdoor patio area with wicker furniture, a pergola structure, and hanging lamps.
The interior of the Four Winds Hotel with a prominent 'Will Call' sign and a large illuminated sign reading 'Alcar Center'.
A spacious atrium with a stone and wood interior, a sign reading "White Birch Market," and a seating area with chairs.

1. Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo
New Buffalo
  • Dive into the seasonal outdoor pool surrounded by loungers, where live music creates a relaxing getaway atmosphere.
S$132
includes taxes & fees
13 Oct - 14 Oct
Four Winds Casino Resort – New Buffalo
An indoor swimming pool with clear blue water, surrounded by lounge chairs and a sun umbrella.
A hotel room with a bed, a desk, a chair, a round table, and a lamp.
A modern lounge area with a fireplace, brown leather sofas, and a patterned rug.
A reception area with a clock, a Holiday Inn Express sign, and a reception desk.

2. Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG
New Buffalo
  • Splash into year-round relaxation with this hotel's immaculate indoor pool, located just minutes from Lake Michigan's shores.
S$162
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Express & Suites New Buffalo by IHG
A modern indoor pool area with a clear view of the outside, a small seating area, and a pool with a visible safety railing.
A spacious living area with a blue sofa, two armchairs, and a brown ottoman. A small table with a lamp is near the window, which has brown curtains.
A hotel lobby with a reception desk, seating area, and a large window with curtains.
A hotel room with two beds, a desk, a TV, and a window with curtains.

3. Quality Inn Near Interstate I94

Quality Inn Near Interstate I94
New Buffalo
  • Sparkling blue waters await at this forest-surrounded hotel, where relaxation comes with refreshing indoor pool dips.
S$98
includes taxes & fees
2 Nov - 3 Nov
Quality Inn Near Interstate I94
A pool area with a tiled floor, lounge chairs, and a table.
A modern dining area with a round table and six chairs, a large pendant light, and a stone accent wall.
A modern hotel lobby with a central bar, seating area, and large windows.
A modern lobby with a reception desk, seating area with green upholstered chairs, a round table, and a staircase leading to an upper level.

4. Fairfield Inn & Suites by Marriott New Buffalo

Fairfield Inn & Suites by Marriott New Buffalo
New Buffalo
  • Splash into indoor poolside fun just moments from Lake Michigan's shores.
S$157
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott New Buffalo
An indoor swimming pool with clear blue water, surrounded by stone walls and large windows.
An outdoor patio area with wicker furniture and a white fence.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A modern kitchen with wooden cabinets, a dining area with tables and chairs, and a refrigerator.

5. Quality Inn Sawyer

Quality Inn Sawyer
Sawyer
  • Splash into year-round aquatic fun at this hotel with its vibrant indoor pool near Lake Michigan.
S$87
includes taxes & fees
1 Nov - 2 Nov
Quality Inn Sawyer
An indoor swimming pool with multiple lanes, surrounded by white lounge chairs and tables.
A bathroom with a white sink, a mirror, a toilet, and a towel rack with towels.
A hotel room with a large bed, a desk with a TV, a bathroom with a bathtub, and a patterned carpet.
A hotel room with a sofa, a white armchair, a desk with a chair, a television, and a door.

6. Baymont by Wyndham New Buffalo

Baymont by Wyndham New Buffalo
New Buffalo
  • Experience poolside relaxation just steps from Lake Michigan with an indoor pool and hot tub escape.
S$105
includes taxes & fees
21 Oct - 22 Oct
Baymont by Wyndham New Buffalo
A bedroom with a bed, a TV mounted on the wall, a coffee machine, and a painting.
A wooden gazebo with a metal roof, seating, and a swing chair.
A row of motel-style buildings with individual units, each featuring a door and a window.
A bathroom with a toilet, a bathtub, and a shower curtain.

7. The Warren Hotel

The Warren Hotel
Bridgman
S$140
includes taxes & fees
25 Oct - 26 Oct
The Warren Hotel
An indoor swimming pool with a glass ceiling, surrounded by lounge chairs and a hot tub.
A beach with waves and a sunset.
A house with a porch, a front door, and a small garden area with plants and pumpkins.
A two-story wooden house with a gabled roof, surrounded by a garden with vibrant pink flowers.

8. Goldberry Woods

Goldberry Woods
Union Pier
  • Sunny splashes await at this Michigan retreat with a refreshing outdoor pool and bubbling hot tub.
S$474
includes taxes & fees
26 Oct - 27 Oct
Goldberry Woods
A spa area with a hot tub, a clock, and a blue door.
A modern bathroom with a large bathtub, a wooden bench, and a tiled backsplash.
A large, multi-story building with a central dome and surrounding structures, surrounded by trees and a parking area.
A hotel room with a large bathtub, a bed, a desk, and a chair.

9. Comfort Suites Stevensville - St. Joseph

Comfort Suites Stevensville - St. Joseph
Stevensville
  • Dive into poolside bliss at this serene hotel with indoor swimming and a rejuvenating hot tub.
S$113
includes taxes & fees
2 Nov - 3 Nov
Comfort Suites Stevensville - St. Joseph
A swimming pool with lounge chairs and a covered area.
A marina with multiple boats docked, calm water, and a clear sky.
A waterfront restaurant with outdoor seating, a covered deck, and a view of the water.
A spacious room with a large bed, a sitting area with a table and chairs, a fireplace, and a view through a sliding glass door.

10. The Blue Heron Inn

The Blue Heron Inn
La Porte
  • Lakeside pool oasis comes alive with sunsets, boat rentals, and creature comforts by Pine Lake.
S$156
includes taxes & fees
13 Oct - 14 Oct
The Blue Heron Inn
View all properties

Choose what matters most at hotels with a pool in Lakeside

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Lakeside Hotel Reviews

Spark by Hilton Stevensville

Spark by Hilton Stevensville

10/10 Excellent
"Clean room and very comfortable bed."
Kendra 1-night trip
Posted 23 hours ago
Spark by Hilton Stevensville
Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"Extremely nice staff. Most comfortable bed. Breakfast was several steps above most hotels. Different items each day, and warm cinnamon rolls. We used the guest laundry too, which was super convenient. Will definitely stay again!"
Michele 3-night trip
Posted 2 days ago
Holiday Inn Express & Suites New Buffalo by IHG
Microtel Inn & Suites by Wyndham Michigan City

Microtel Inn & Suites by Wyndham Michigan City

10/10 Excellent
"We were very impressed with this hotel. My mom said this was the best hotel that she had stayed at in years. She was really impressed with how brightly lit the room was. There were full size mirrors behind the beds with full length lights behind the beds. They were also recess can lights throughout the room. It smelled clean and fresh. It was absolutely perfect. We would love to stay there again. The breakfast was amazing! Delicious hot eggs, biscuits, gravy, bagels with cream cheese, orange juice and much more. A nice indoor pool. The manager was extremely helpful and friendly. Great place very well maintained!"
Justin 1-night trip
Posted 4 days ago
Microtel Inn & Suites by Wyndham Michigan City

Frequently asked questions

What are some accommodation options with pools in Lakeside?
Four Winds Casino Resort – New Buffalo: Cottage, 3-minute walk from Lake Michigan. Features sunloungers, a communal pool and complimentary wireless Internet access. Blue Chip Casino Hotel and Spa: Hotel steps from Four Winds Casino New Buffalo. Provides 4 restaurants, a seasonal outdoor pool and 3 bars. Pine Lake Resort and Banquets: Offers a seasonal outdoor pool, an indoor pool and a full-service spa. Quality Inn Near Interstate I94: Hotel located near Lake Michigan. Features on-the-go, an indoor pool and free self parking. Holiday Inn Express & Suites New Buffalo by IHG: Hotel located near Lake Michigan. Offers buffet, an indoor pool and free self parking.
What is there to see and do in Lakeside?
Explore places such as Lake Michigan while you're in Lakeside. Make a point to visit attractions such as Round Barn Union Pier Tasting Room and New Buffalo Railroad Museum.
When is the best time to book a hotel with a pool in Lakeside?
You may want to consider accommodation that offers an outdoor pool if you're planning to visit Lakeside in the warmest months of July, August or June, when the average temperature is 21°C. Accommodation with an indoor pool may be what you want if you visit during the coldest months of January, February or December, when the average temperature is 0°C.

Explore a world of travel with Expedia