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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 10 B&B in Kaupo with updated reviews, rates, and availability.

Charming bed & breakfast on the slopes of Haleakala with AC, WiFi.
Interior

Charming bed & breakfast on the slopes of Haleakala with AC, WiFi.

9.4 out of 10, Exceptional, (19)
"Ok place. Convenient place to spend night before going to park for sunrise."
The price is AED 661
AED 1,611 total
includes taxes & fees
10 May - 11 May
Charming bed & breakfast on the slopes of Haleakala with AC, WiFi.
Hana Garden Room 1 & 2 night stays, its Perfect! Longer stays available.
Interior

Hana Garden Room 1 & 2 night stays, its Perfect! Longer stays available.

8.6 out of 10, Excellent, (21)
"We spent a peaceful night in this nice condo. The fruit provided was delicious and the hosts were great."
The price is AED 863
AED 1,149 total
includes taxes & fees
8 May - 9 May
Hana Garden Room 1 & 2 night stays, its Perfect! Longer stays available.
Relaxing Hawaiian Suite for a Exiting Getaway in the Upcountry of Maui!
Pool

Relaxing Hawaiian Suite for a Exiting Getaway in the Upcountry of Maui!

10.0 out of 10, Exceptional, (22)
"Natural beauty abounds!"
Relaxing Hawaiian Suite for a Exiting Getaway in the Upcountry of Maui!
Spacious Hawaiian Cottage Suite in the Upcountry of Maui!
Pool

Spacious Hawaiian Cottage Suite in the Upcountry of Maui!

10.0 out of 10, Exceptional, (9)
"We very much enjoyed our peaceful and relaxing, but all too short stay at your "remote" and beautiful location. Our room, The Duke, was nicely furnished and large. Altogether, North Shore Lookout is a delightful B&B with great grounds and views. Would like to come back."
Spacious Hawaiian Cottage Suite in the Upcountry of Maui!
Relaxing Hawaiian Suite for a Romantic Getaway in the Upcountry of Maui!
Pool

Relaxing Hawaiian Suite for a Romantic Getaway in the Upcountry of Maui!

10.0 out of 10, Exceptional, (2)
"Exceeded our expectations! From the easy check-in to the incredible breakfasts, the old-school pool and hanging garden, and an unexpected herd of deer running through the property, this was one of the most relaxing and tranquil escapes we’ve experienced. The town of Makawao gave us tasty afternoon meals (Satori!) and the beautiful mountain area provided plenty of scenic driving. Only advice I’d give is to plan to enjoy the space while you’re staying, as it would be a shame to not settle in....
Relaxing Hawaiian Suite for a Romantic Getaway in the Upcountry of Maui!
Relaxing upcountry retreat on the slopes of Haleakalā. Ideal for families.
Property grounds

Relaxing upcountry retreat on the slopes of Haleakalā. Ideal for families.

Relaxing upcountry retreat on the slopes of Haleakalā. Ideal for families.
Spacious Hawaiian Suite for a Romatic Getaway in the Upcountry of Maui!
Terrace/patio

Spacious Hawaiian Suite for a Romatic Getaway in the Upcountry of Maui!

10.0 out of 10, Exceptional, (7)
"Great property & location, excellent hosts!"
Spacious Hawaiian Suite for a Romatic Getaway in the Upcountry of Maui!
Modern Upcountry Hawaiian Suite for a Romantic Getaway in the Upcountry of Maui!
Terrace/patio

Modern Upcountry Hawaiian Suite for a Romantic Getaway in the Upcountry of Maui!

2.0 star property
10.0 out of 10, Exceptional, (1)
"We stayed 3 nights. This was the first time to stay upcountry and we were pleasantly surprised by the contrast of the slower pace from the beach areas. Greeted with a smile by Josh as we came to the entry door and he explained about check in. The house is newly renovated, welcoming and very clean all over. The suite is huge, comfortable and private. Shower has plenty of hot water and pressure. We had lovely and tasty breakfast with some items changed every day. Josh will make Latte on request....
Modern Upcountry Hawaiian Suite for a Romantic Getaway in the Upcountry of Maui!
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 Kaupo

STHA-2017/0002 Across from Hana Bay
Beach towels

STHA-2017/0002 Across from Hana Bay

9.6 out of 10, Exceptional, (372)
"My favorite part of the property was the outdoor bed on the screen-in porch, had the best night of sleep of my whole vacation sleeping outside"
STHA-2017/0002 Across from Hana Bay
Oceanview Condo in Hana-Let the ocean lull you to sleep
Outdoor dining

Oceanview Condo in Hana-Let the ocean lull you to sleep

9.2 out of 10, Wonderful, (91)
"Wish we could stay longer!"
The price is AED 856
AED 1,627 total
includes taxes & fees
7 May - 8 May
Oceanview Condo in Hana-Let the ocean lull you to sleep
Wailea Ekolu - CoralTree Residence Collection
2 outdoor pools

Wailea Ekolu - CoralTree Residence Collection

3.5 star property
8.8 out of 10, Excellent, (253)
"Amazing place to stay! Great area, stunning views. Very walkable "
Wailea Ekolu - CoralTree Residence Collection
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.

Frequently asked questions

Searching for B&Bs in Kaupo?
Whether you’re on a family vacation and want a small, cozy place to stay, or you’re traveling solo and hoping to get some local recommendations, B&Bs can be a great choice for many types of vacationers. If your ideal vacation to Kaupo includes spending lots of time outside, Haleakala National Park is a good spot to enjoy the scenery.
How do you know if a B&B is the best choice for your stay?
Every B&B has a unique charm. Whether it’s a comfy common area with a fireplace or a beautiful breakfast room, the quaint details are what make bed and breakfasts a home away from home.
What are the best B&Bs in Kaupo?
Here are some B&Bs in the surrounding area: Hana Garden Room 1 & 2 night stays, its Perfect! Longer stays available.: 11.6 mi (18.6 km) from the heart of Kaupo.Relaxing upcountry retreat on the slopes of Haleakalā. Ideal for families.: Situated 16.8 mi (27 km) from the heart of Kaupo.
When is the best time to book my B&B in Kaupo?
When you’re dreaming of a stay in Kaupo, be sure to take into account the year-round temperatures. The hottest months are usually August and September with an average temp of 75°F, while the coldest months are March and February with an average of 71°F. Average annual precipitation for Kaupo is 40 inches.
What is there to do in Kaupo?
If you want to check out some popular attractions in Kaupo, you might enjoy a visit to Haleakala National Park. Wailua Falls and Haleakalā Visitor Center are also some sites to visit if you want to see more of the area.
How can I get to and around Kaupo?
Planning your excursions in and around Kaupo is easier with these transportation options. Fly into Hana, HI (HNM), which is located 12.9 mi (20.7 km) away from the heart of the city. You can also search for flights into Kahului Airport (OGG), which is 26.8 mi (43.1 km) away. If you’d like to venture out around the area, consider renting a car to take in more sights.