We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows:
Internet Explorer
,
Mozilla Firefox
,
Google Chrome
. Mac:
Safari
.
Flights
Holiday Rentals
Restaurants
Things to do
Skip to main content
Discover
Trips
Review
More
GBP
Sign in
Highland
Hotels
Things to Do
Restaurants
Flights
Holiday Rentals
Cruises
Car Hire
Forums
Inbox
See all
Log in
to get trip updates and message other travellers.
Cottages, Villas, Apartments in Highland
Holiday Rentals
USA
Wisconsin (WI)
Cottages, Villas, Apartments in Highland
Search
Owner log in
Highland
Holiday Rentals
Destination
Check In
Check Out
Guests
2 Guests
Map
Tripadvisor Sort
Revenue impacts this sort order.
Learn more
Bedrooms
Any
Bathrooms
Any
Amenities
Air Conditioning (46)
Internet or Wifi (44)
Grill (35)
Other outdoor space (29)
Show all
Suitability
Kid friendly (40)
Pet friendly (10)
Smoking allowed (2)
Wheelchair access (0)
Show more
Property type
Holiday Rental House (42)
Condominium/Apartment (4)
Cabin Holiday Rental (0)
Private Room (0)
Show more
Distinctive Features
Waterfront (3)
Boat Available (1)
Private Chef (0)
Private Beach (0)
Show all
Distance from
5 mi
Blackhawk Lake Recreation Area
Spurgeon Vineyards & Winery
Bootleggers
Gopher Hole Lounge
Show all
46 rentals
in Highland.
Vermont West - Beautiful, Private, Serene Home Away from Home
13
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Farmhouse Lodge, Private 4-bedroom, Hot tub, Massage Chair, spacious, AC 5G,
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 9
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
The following properties within 20 miles of Highland match all your filters:
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
5,450
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Serenity Cottage at Mineral Point
39
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin
33
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Enjoy peaceful surroundings
28
Holiday Rental House
View on map
4 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Unique! A renovated old railroad depot turned into a cozy cottage.
96
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Driiftless Cottage
16
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Riverside Chalet, LLC
36
Holiday Rental House
View on map
3 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Amish-Built Cabin in the Driftless Area
25
Holiday Rental House
View on map
4 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Close to Local Opera House - On the main drag
27
Condo/Apartment
View on map
3 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Scenic Luxury Cabin, Secluded Woods, Blue Ribbon Trout Stream
117
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 7
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
65
Holiday Rental House
View on map
6 bedrooms
4 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
A Comfy Cozy Cottage on Clowney
16
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
River's Edge Cabin, LLC
33
Holiday Rental House
View on map
4 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Serenity awaits at this secluded riverfront property
31
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Relax with beautiful views overlooking the Wisconsin River
27
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Spacious Cabin on the Wisconsin River!
13
Holiday Rental House
View on map
5 bedrooms
4 bathrooms
Sleeps 18
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Rustic, small and primitive cabin - Riverview Cabin, LLC
18
Holiday Rental House
View on map
3 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Beautiful land mark property 15 mins from the Wisconsin river and lake
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Serenity!!
11
Condo/Apartment
View on map
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
The Cabin at Big Valley Ranch
10
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Historic Cottage in Spring Green, Wisconsin
16
Holiday Rental House
View on map
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Cottage on Main
5
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
On 278 pristine acres, 1 acre fishpond, close to all Spring Green attractions!
10
Holiday Rental House
View on map
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Exclusive Western Themed Retreat With 800 Acres To Enjoy
29
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Private Ridge top Cabin/House
4
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Entire 3 Bedroom House + Huge Wooded Yard
3
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 7
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
The Yellow Farm
13
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Eco-Friendly/Sustainable White Oak Savanna Events Farm & Sanctuary
16
Holiday Rental House
View on map
4 bedrooms
2 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
The Lodge at Big Valley Ranch
10
Holiday Rental House
View on map
6 bedrooms
3 bathrooms
Sleeps 14
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
The Barn at Big Valley Ranch
42
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Rustic, Elegant 8,000 Sq. Ft. Timber Frame Lodge in Southwest Wisconsin.
14
Holiday Rental House
View on map
8 bedrooms
5 bathrooms
Sleeps 19
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Elegant country retreat near Spring Green w expansive views of Driftless Region
22
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Relaxation cabin at Crooked Creek
Holiday Rental House
View on map
1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Serenity cabin at Crooked Creek
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Elderflower Retreat: a modern ranch overlooking the valley with view of Taliesin
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 9
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly
14
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
River Road Getaway
9
Holiday Rental House
View on map
3 bedrooms
1 bathroom
Sleeps 9
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Quaint & Quiet 2 bed 1 bath
Condo/Apartment
View on map
1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Silver Birch Retreat. Spacious, pet friendly country home
6
Holiday Rental House
View on map
4 bedrooms
2 bathrooms
Sleeps 13
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Rustic Cabin at Crooked Creek
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Hotel Royal Apartment 2
Condo/Apartment
View on map
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Escape to The Skogen "Where Memories are Made" near Dodgeville WI
Holiday Rental House
View on map
1 bedroom
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Deerfield Bottom
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
River Road Retreat
9
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
1
Showing results 1-46 of 46
Frequently Asked Questions about Highland
Do any holiday rentals in Highland have a pool?
Yes, here are some popular holiday rentals in Highland that have a pool:
Vermont West - Beautiful, Private, Serene Home Away from Home
Farmhouse Lodge, Private 4-bedroom, Hot tub, Massage Chair, spacious, AC 5G,
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
See all holiday rentals with a pool in Highland on Tripadvisor
Do any holiday rentals in Highland have internet access?
Yes, here are some popular holiday rentals in Highland that have internet access:
Vermont West - Beautiful, Private, Serene Home Away from Home
Farmhouse Lodge, Private 4-bedroom, Hot tub, Massage Chair, spacious, AC 5G,
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
See all holiday rentals in Highland on Tripadvisor
What are the best pet friendly rentals in Highland?
The best pet friendly rentals in Highland are:
Vermont West - Beautiful, Private, Serene Home Away from Home
Farmhouse Lodge, Private 4-bedroom, Hot tub, Massage Chair, spacious, AC 5G,
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
See all pet friendly holiday rentals in Highland on Tripadvisor
What are some great rentals in Highland that are kid friendly?
Some of the most popular kid friendly rentals in Highland are:
Vermont West - Beautiful, Private, Serene Home Away from Home
Farmhouse Lodge, Private 4-bedroom, Hot tub, Massage Chair, spacious, AC 5G,
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
See all kid friendly holiday rentals in Highland on Tripadvisor
Highland
Highland Tourism
Highland Hotels
Highland Holiday Rentals
Flights to Highland
Highland Restaurants
Highland Attractions
Highland Travel Forum
Highland Photos
Highland Map
Highland Guide
Hotels
All Highland Hotels
Highland Hotel Deals
By Hotel Class
5-stars Hotels in Highland
4-stars Hotels in Highland
3-stars Hotels in Highland
Near Airports
Hotels near (DBQ) Dubuque Municipal Airport
Things to Do
Restaurants
Flights
Holiday Rentals
Travel Stories
Cruises
Car Hire
More
Tours
Add a Place
Travel Forum
Airlines
Travellers' Choice
Help Centre
Travel Stories