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Compare 185 Vacation Homes in Highland with updated reviews, rates, and availability.

Casa Blanca in Miller Beach!
9.8 out of 10, Exceptional, (65)
"The whole family enjoyed our stay and loved the location to the beach. We had a wonderful time."
Casa Blanca in Miller Beach!
Cozy Home Sweet Homewood.
10.0 out of 10, Exceptional, (14)
"My mom and I live in Huntsville Alabama and came to visit family and friends in the area and the Homewood house was the perfect location to stay. I miss home so much. It was very comfortable and cute. I will definitely make reservations for next year. Forget staying in a hotel. 😉😅"
Cozy Home Sweet Homewood.
Pet-Friendly Lake Getaway: 1 Block to Beach!
10.0 out of 10, Exceptional, (34)
"Property was very clean and photos accurate. Check in process was easy and we enjoyed a quick fall weekend get away to hike the Dunes. Good communication from owner. Thanks!"
Pet-Friendly Lake Getaway: 1 Block to Beach!
Nestled just behind Marquette Park. 5 minute walk to beach.
10.0 out of 10, Exceptional, (9)
"Could not be more thankful for her prompt replies and accommodations."
Nestled just behind Marquette Park. 5 minute walk to beach.
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
9.8 out of 10, Exceptional, (8)
"Would reserve this again wonderful host"
The price is AED 290
AED 407 total
includes taxes & fees
1 Dec - 2 Dec
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
8.6 out of 10, Excellent, (32)
"We enjoyed our stay at Sandhill Flat. The check in process was easy and communication was clear. The place is spacious, clean and stocked well. I was impressed they provided some coffee and sugar packets. We enjoyed the spacious backyard, grill and hot tub in the evenings. We were close to the park and beach . We would return."
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.
10.0 out of 10, Exceptional, (14)
"We had an excellent experience at this property. The home is very cute and has everything you need. Attentive management. We will definitely come back!"
Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.
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
LakeHouse
10.0 out of 10, Exceptional, (13)
"Overall great experience! Great home, I love the decor of the entire home. And I will definitely recommend to others and will book again "
LakeHouse
Cheerful 4 bedroom smart home w/ indoor fireplace
7.8 out of 10, Good, (12)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace
Newly Renovated with Finished Basement
9.8 out of 10, Exceptional, (73)
"My 3 girlfriends and I enjoyed staying at this spacious comfortable clean home. We would love to visit again when we are back visiting the Portage area. Thank you!"
The price is AED 511
AED 1,115 total
includes taxes & fees
18 Nov - 19 Nov
Newly Renovated with Finished Basement
An Escape to a Dream of Green and relaxation.
10.0 out of 10, Exceptional, (11)
"Thoroughly enjoyed our stay at this lovely home. It was clean, comfortable, and well equipped. The beds in particular made for the best sleep I have had in a long time. "
An Escape to a Dream of Green and relaxation.
Welcome to Boss Barbie’s Dreamhouse! Everything is pink.
9.8 out of 10, Exceptional, (7)
"It was everything we imagined it to be!!!"
Welcome to Boss Barbie’s Dreamhouse! Everything is pink.
Steps to Lake Michigan Beach: Gary Vacation Rental
9.2 out of 10, Wonderful, (34)
"Nice"
Steps to Lake Michigan Beach: Gary Vacation Rental
Lux Home in Chicago 7mins Downtown
9.8 out of 10, Exceptional, (13)
"Lovely house. Host was responsive to questions during our stay. "
Lux Home in Chicago 7mins Downtown
Restored Cottage Across The Street From The Beach!
9.8 out of 10, Exceptional, (94)
"5th year in this great house steps from the beach. Everything you need."
Restored Cottage Across The Street From The Beach!
Beautiful Modern Historic Greystone - Near Lake Michigan- Free Parking
5.4 out of 10, (3)
"the unit had plenty of room; the internet was fast and we watched a long movie on Netflix. Everything was clean and comfortable and there was plenty of soaps and towels. Close to Washington Park so we walked there every day. Quiet neighborhood, safe location, we didn't want to leave."
Beautiful Modern Historic Greystone - Near Lake Michigan- Free Parking
Beautiful Bronzeville Duplex!
10.0 out of 10, Exceptional, (2)
"Beautiful, clean home in a good area. Host responded quickly to any questions. Would definitely book again."
Beautiful Bronzeville Duplex!
Modern FarmHouse Stay On 12 Acres with Fireplace and Hot Tub, Sleeps 16
10.0 out of 10, Exceptional, (13)
"This home was ideal for my family’s need and it couldn’t have been better. Highly recommended."
Modern FarmHouse Stay On 12 Acres with Fireplace and Hot Tub, Sleeps 16
Panoramic views, Hot Tub, Sauna, Firepit, Sand Vball, Foosball, Dunes Nat'l Park
9.2 out of 10, Wonderful, (63)
"The home was just as it was listed. The host staff was fantastic with working with us. The house was very nice and had all the needs you need"
Panoramic views, Hot Tub, Sauna, Firepit, Sand Vball, Foosball, Dunes Nat'l 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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Other property types in Highland

Skyline Views, Hot Tub, Beachfront, Lavish Kitchen at Dunetop Villa
9.2 out of 10, Wonderful, (45)
"Our family had a very good time enjoying house beach and national park "
Skyline Views, Hot Tub, Beachfront, Lavish Kitchen at Dunetop Villa
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community
9.4 out of 10, Exceptional, (12)
"Thank you for the great stay. I really appreciate the little touches like the bath bomb. Much needed. Communication was great. Good location to stay. "
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
9.8 out of 10, Exceptional, (66)
"Rented with Valane for the marathon weekend. It was clean, quiet, away from the hustle of the city. It was super easy to navigate to expo, start lines, and sites. Loved jot beong couped up in a hotel room for the weekend Highly recommend Thank you so much for the great stay"
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
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.