Holiday Homes in Cook County

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Cook County

200’ of your own private accessible Lake Superior Shore: Stony Shores Retreat
Interior

200’ of your own private accessible Lake Superior Shore: Stony Shores Retreat

9.4 out of 10, Exceptional, (173)
"The highlight of this property is the location. It's close to so many great places to explore and the lot is beautiful. The view and access to the lake is unbeatable and the grounds are fantastic and well-maintained. We had some housekeeping concerns when we arrived; the property manager responded quickly and was very friendly but would obviously prefer not to start a vacation with any issues. "
200’ of your own private accessible Lake Superior Shore: Stony Shores Retreat
Beautiful Minnesota Townhome on Lake Superior ~ Incredible View
On the beach

Beautiful Minnesota Townhome on Lake Superior ~ Incredible View

9.8 out of 10, Exceptional, (151)
"The property was much better than depicted in the VRBO description. "
Beautiful Minnesota Townhome on Lake Superior ~ Incredible View
A view of Lake Superior set in the middle of a working farm
Interior

A view of Lake Superior set in the middle of a working farm

10.0 out of 10, Exceptional, (123)
"Stunning views, gentle mooing, lovely house! Thank you!!"
A view of Lake Superior set in the middle of a working farm
Northern Comfort Overlooking Caribou Lake- Spacious and Secluded
Fridge, microwave, oven, stovetop

Northern Comfort Overlooking Caribou Lake- Spacious and Secluded

10.0 out of 10, Exceptional, (225)
"First impressions as walk was oh my god all the woodm after entering its dang more wood. The views were respendant and the noise wass outdoors with the rare car far off in the distance. Location was easy to get to. We thoroughly enjoyed the trip and the relaxation. Many thanks for sharing your space with us."
Northern Comfort Overlooking Caribou Lake- Spacious and Secluded
Ski-in Ski-out Townhome with pool + hot tub!
Indoor pool, outdoor pool

Ski-in Ski-out Townhome with pool + hot tub!

9.6 out of 10, Exceptional, (30)
"Nice property. Clean. Communication with host was excellent. Would visit again. "
Ski-in Ski-out Townhome with pool + hot tub!
North Shore Escape, Lutsen Mtn., Ski In/Ski Out at Lutsen Mountains
Outdoor dining

North Shore Escape, Lutsen Mtn., Ski In/Ski Out at Lutsen Mountains

8.8 out of 10, Excellent, (29)
"It was a great location and size for our family. The house had a few quirks and updates needed but overall was perfect for our quick trip to the North Shore. "
North Shore Escape, Lutsen Mtn., Ski In/Ski Out at Lutsen Mountains
Adventure Oasis: All-Season Sport Haven, Ski-in/Ski-out
Outdoor dining

Adventure Oasis: All-Season Sport Haven, Ski-in/Ski-out

10.0 out of 10, Exceptional, (88)
"We were very happy with the communication and everything was well stocked. It was a perfect space for our family time together. "
Adventure Oasis: All-Season Sport Haven, Ski-in/Ski-out
Private Home on 10 Acres of Wilderness. 15 min to Lutsen. Dog Friendly.
Property grounds

Private Home on 10 Acres of Wilderness. 15 min to Lutsen. Dog Friendly.

10.0 out of 10, Exceptional, (1)
"We had a wonderful stay here for our 4th wedding anniversary with our two dogs! Cabin was clean, cozy, and easy to find. Katie messages back quickly, and was overall amazing! We can’t wait to come back! "
Private Home on 10 Acres of Wilderness. 15 min to Lutsen. Dog Friendly.
Fantastic House In Grand Marais! Walking Distance To Downtown!
Interior

Fantastic House In Grand Marais! Walking Distance To Downtown!

10.0 out of 10, Exceptional, (232)
"Property was very clean, and had everything we needed for a short stay. We especially enjoyed the ping pong table, and a visiting kitty who checked on us every day. Nice outdoor spaces too, we had a bonfire one nite and it was very easy to do. Walkable to downtown and the harbor. "
Fantastic House In Grand Marais! Walking Distance To Downtown!
Walk Anywhere in Grand Marais from This Charming Bungalow:

Walk Anywhere in Grand Marais from This Charming Bungalow:

9.4 out of 10, Exceptional, (70)
"We enjoyed our time here while we were in town for a North Folk School class, just a block or so away. "
Walk Anywhere in Grand Marais from This Charming Bungalow:
Basecamp for Your North Shore/Lutsen Adventures
Smart TV, fireplace

Basecamp for Your North Shore/Lutsen Adventures

10.0 out of 10, Exceptional, (17)
"We had a wonderful time! Plenty of room for 8 adults! Would rent again for sure! "
Basecamp for Your North Shore/Lutsen Adventures
20 3rd Ave., West and first Street.Great harbor view Right in the heart of town.
Interior

20 3rd Ave., West and first Street.Great harbor view Right in the heart of town.

10.0 out of 10, Exceptional, (132)
"This house is in a perfect location in GM! We walked all over and enjoyed the view of the lake. The house is cozy and clean and had everything we needed. We contacted the host once with a question and he was gracious and charming and funny. Would recommend and stay here again. "
20 3rd Ave., West and first Street.Great harbor view Right in the heart of town.
Tofte - Lake Superior Lakefront Retreat w/Balcony
Aerial view

Tofte - Lake Superior Lakefront Retreat w/Balcony

10.0 out of 10, Exceptional, (43)
"A beautiful property, a beautiful view, and a wonderful property owner. "
The price is AU$772
includes taxes & fees
1 Dec - 2 Dec
Tofte - Lake Superior Lakefront Retreat w/Balcony
Saganaga Lodge Small Room #2
Outdoor dining

Saganaga Lodge Small Room #2

9.6 out of 10, Exceptional, (30)
"It was fun to canoe on the lake when we arrived after a long dry ve."
The price is AU$219
includes taxes & fees
30 Nov - 1 Dec
Saganaga Lodge Small Room #2
A River Runs Through It
Property grounds

A River Runs Through It

10.0 out of 10, Exceptional, (205)
"A well-equipped cabin in a beautiful setting. A nice get-away. We loved the stream."
A River Runs Through It
The Skolhaus, your Cozy family-sized base camp, on the trails in Lutsen!
Smart TV, fireplace, DVD player, books

The Skolhaus, your Cozy family-sized base camp, on the trails in Lutsen!

8.8 out of 10, Excellent, (16)
"We enjoyed staying here! Skiing in and out was great!"
The Skolhaus, your Cozy family-sized base camp, on the trails in Lutsen!
Stone Arch- Entire Large Home on Unique Lake Superior Shoreline
Exterior

Stone Arch- Entire Large Home on Unique Lake Superior Shoreline

10.0 out of 10, Exceptional, (40)
"Living/dining room has Lake view, roomy & relaxing for our 8 adults/2 kids for a week. We knew no washer/dryer but regretted it. Someone had to sit in Grand Marais laundromat while others had fun. Bedrooms roomy! Some had shelves instead of dressers, some lacked blackout blinds, heat downstairs uneven, some had nightstand with lamp on only one side of the bed. Probably a one time thing, but kitchen chopping board was caked with food & smelly stuff in waste basket. Enjoyed the pool table. Good...
Stone Arch- Entire Large Home on Unique Lake Superior Shoreline
The SkyHouse- Life as Art- Sauna Available
Exterior detail

The SkyHouse- Life as Art- Sauna Available

10.0 out of 10, Exceptional, (97)
"Fastest way to feel like you’re in Northern Europe "
The SkyHouse- Life as Art- Sauna Available
"North Shore Retreat" Lutsen 5 Bed/4 Bath, Sleeps 14, Ski in - Ski out
Beach

"North Shore Retreat" Lutsen 5 Bed/4 Bath, Sleeps 14, Ski in - Ski out

10.0 out of 10, Exceptional, (239)
"We loved having the space for our 3 families. Everyone was happy!"
"North Shore Retreat" Lutsen 5 Bed/4 Bath, Sleeps 14, Ski in - Ski out
Lakefront retreat, river/wood fireplace/hot tub
Miscellaneous

Lakefront retreat, river/wood fireplace/hot tub

10.0 out of 10, Exceptional, (8)
"Beautiful home, super clean, picturesque setting and fabulous hosts! We can’t wait to return! "
Lakefront retreat, river/wood fireplace/hot tub
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.
Don't see what you're looking for?
See all available properties in Cook County
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals