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Check prices for these dates

Next weekend
Aug 22 - Aug 24
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Aug 29 - Aug 31
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Sep 12 - Sep 14
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Oct 10 - Oct 12

Browse Select Highland Vacation Homes

Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Fridge, microwave, oven, stovetop

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

7.4 out of 10, Good, (8)
"Very communicative and good host for sure!"
The price is CA $179
CA $461 total
includes taxes & fees
Aug 19 - Aug 20
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Cozy Home Sweet Homewood.
Fridge, microwave, oven, stovetop

Cozy Home Sweet Homewood.

9.6 out of 10, Exceptional, (32)
"Nice location outside of Chicago, cozy and clean, good communication, would definitely recommend! "
Cozy Home Sweet Homewood.
LakeHouse
Fridge, microwave, oven, stovetop

LakeHouse

9.2 out of 10, Wonderful, (20)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
Outdoor dining

Charming 1-bedroom apt in house by creek with AC, in delightful Portage

10.0 out of 10, Exceptional, (4)
"Easy check in and wonderful host. Great place to stay near Indiana Dunes and train station to Chicago. "
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Terrace/patio

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

8.4 out of 10, Very good, (37)
"The yard is awesome, of course the hot tub at the top of the hill was the best, and we enjoyed the firepit as well. The house was a tidy little cottage at which we enjoyed our stay. It’s within a short walk to the National Park and downtown Miller Beach. The neighborhood is fine, pretty secluded, and still close to most attractions."
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Spacious 4-bedroom Getaway in Portage, Perfect for family get togethers
Terrace/patio

Spacious 4-bedroom Getaway in Portage, Perfect for family get togethers

8.8 out of 10, Excellent, (3)
"Spacious. Good outdoor area"
Spacious 4-bedroom Getaway in Portage, Perfect for family get togethers
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Terrace/patio

Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

8.8 out of 10, Excellent, (40)
"We had a great stay! The property was perfect- hot tub, plenty of beds, comfortable beds, walking distance to Lake Michigan! Home was comfortable and clean and the managers were easy to reach with questions-just a text away. Would definitely stay here again"
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
Fridge, microwave, oven, stovetop

15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

8.6 out of 10, Excellent, (13)
"Great place, nice location and the Hosts are extremely good to work with. Highly recommend this just out of the city stay!"
The price is CA $286
CA $698 total
includes taxes & fees
Aug 13 - Aug 14
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
Microwave, oven, stovetop, coffee/tea maker

13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/

2.0 star property
8.0 out of 10, Very good, (4)
"Host was very nice and communicative! Kindly answered all my questions and made our stay amazing. Thanks! "
The price is CA $400
CA $909 total
includes taxes & fees
Aug 13 - Aug 14
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake
Smart TV, fireplace, foosball

Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake

2.0 star property
10.0 out of 10, Exceptional, (13)
"This was a central location for us to meet with friends, nice accommodations, and a little bit of everything nearby.Hostess was so kind and helpful; house was great and fun for a relaxing weekend from space, to a large fenced backyard to the fire pit. Great place!"
The price is CA $351
CA $764 total
includes taxes & fees
Aug 14 - Aug 15
Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake
The Family Retreat, The Family Retreat Oasis
Property grounds

The Family Retreat, The Family Retreat Oasis

2.0 out of 10, (1)
The Family Retreat, The Family Retreat Oasis
Pet-Friendly Lake Getaway: 1 Block to Beach!
Fridge, microwave, stovetop, dishwasher

Pet-Friendly Lake Getaway: 1 Block to Beach!

10.0 out of 10, Exceptional, (41)
"The property was perfect for our family! It was such a quick walk to the beach that I was able to take multiple beach walks between short rain showers. It was also close enough that we walked to grab pizza for the kids. The host was super communicative and accommodating. I would definitely stay here again! "
Pet-Friendly Lake Getaway: 1 Block to Beach!
Moody Modern Dunes • Hot tub + Beaches & Trails
3 bedrooms, desk, iron/ironing board, travel crib

Moody Modern Dunes • Hot tub + Beaches & Trails

10.0 out of 10, Exceptional, (1)
"This was one of the nicest, cleanest VRBO we have stated in. Don’t let the neighborhood detour you from staying. We felt safe and slept amazing in the VERY comfy king bed !! The master shower drain wasn’t working during our stay but the owner was very responsive and apologized for the inconvenience. "
Moody Modern Dunes • Hot tub + Beaches & Trails
Cozy Cabin w/ Loft, Grill and Fire Pit
Interior

Cozy Cabin w/ Loft, Grill and Fire Pit

The price is CA $260
CA $542 total
includes taxes & fees
Aug 21 - Aug 22
Cozy Cabin w/ Loft, Grill and Fire Pit
Relaxing hot and beautiful 4 bed, 2 baths in peaceful area
Private kitchen

Relaxing hot and beautiful 4 bed, 2 baths in peaceful area

4.0 out of 10, (4)
"There was room enough for everyone. I like the recording ring doorbell. I like bathroom connect to bedroom. I didn’t like the wide open vent in the floor leading to bathroom. The bathroom door is on backwards. The coffee pot was molded. There were plenty of towels and washcloths. The bed is too close to the wall. The neighborhood is nice and quiet. I probably would stay there again but the price was high for the condition of the house. This house needs a lot of maintenance."
Relaxing hot and beautiful 4 bed, 2 baths in peaceful area
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Exterior detail

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

2.0 star property
10.0 out of 10, Exceptional, (6)
"Very clean in a safe neighborhood. I would stay here again"
The price is CA $219
CA $307 total
includes taxes & fees
Aug 28 - Aug 29
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach
Beach nearby, sun loungers

Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach

10.0 out of 10, Exceptional, (37)
"Amazing stay, and beautiful surroundings "
Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach
Cozy house in Schererville, IN
Exterior detail

Cozy house in Schererville, IN

10.0 out of 10, Exceptional, (15)
"Perfect for the perfect couples getaway"
The price is CA $223
CA $495 total
includes taxes & fees
Aug 17 - Aug 18
Cozy house in Schererville, IN
Remodeled Charming Home,Backyard w/Pergola,Pool/Ping Pong Game Room, Homewood IL
Terrace/patio

Remodeled Charming Home,Backyard w/Pergola,Pool/Ping Pong Game Room, Homewood IL

10.0 out of 10, Exceptional, (3)
"We had a lot of fun and the host were so helpful and respectful and the place was worth every penny. I highly recommend and of course I will rent again if I go back to Chicago "
Remodeled Charming Home,Backyard w/Pergola,Pool/Ping Pong Game Room, Homewood IL
Dreamsville Gateway to Indiana Dunes National Park
Exterior

Dreamsville Gateway to Indiana Dunes National Park

6.0 out of 10, (1)
"Listed as private home , once you get there and read the house rules it states shared refrigerator with owner. Owner comes in while you are gone and turns off all lights and the Ac, even goes into your locked room to turn off ac."
Dreamsville Gateway to Indiana Dunes National Park
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Highland Hotel Reviews

Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

10/10 Excellent
"Good "
Charles 1-night trip
Posted 1 day ago
Motel 6 - Chicago, IL