Search Cottages in Windward Coast

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sep - 7 Sep
In two months
3 Oct - 5 Oct

Cottages in Windward Coast

Bright, clean, airy Rocky Point Beach 1 bedroom loft. Steps to beach & bike path
Beach nearby, sun loungers, beach towels

Bright, clean, airy Rocky Point Beach 1 bedroom loft. Steps to beach & bike path

9.6 out of 10, Exceptional, (219)
"We stayed for two weeks and the property was the perfect place to stay on the North Shore. The property has everything you need for your stay. It is very open planned and with the windows open a refreshing breeze blows through. It is also located beside the beach, which from what we could make out only has residents of the area there. Parking was never an issue to find on the street. It takes about 15 minute drive to beautiful Haleiwa and around 50 mins to an hour to Honolulu. We couldn’t...
Bright, clean, airy Rocky Point Beach 1 bedroom loft. Steps to beach & bike path
An Absolute, Perfect Paradise and Affordable
Exterior

An Absolute, Perfect Paradise and Affordable

9.6 out of 10, Exceptional, (159)
"Stay was simply wonderful! Turtles galore and Terries property is the sweetest of all the cottages! Terries sweet all day long as well. Seriously this stay will make you come back for more. "
An Absolute, Perfect Paradise and Affordable
Breathtaking Ocean Views Beach Cottage
Exterior

Breathtaking Ocean Views Beach Cottage

9.4 out of 10, Exceptional, (143)
"We loved our stay here. You really are right on the beach; I was wondering if the pictures would be accurate but the beach is even BETTER than pictured. A magical time for our family. Book it!"
Breathtaking Ocean Views Beach Cottage
Seaside Paradise
Property grounds

Seaside Paradise

9.4 out of 10, Exceptional, (193)
"The stay was everything we imagined and then some."
Seaside Paradise
Beachfront Cottage at Log Cabins
Outdoor dining

Beachfront Cottage at Log Cabins

9.6 out of 10, Exceptional, (37)
"Awesome location Great host"
Beachfront Cottage at Log Cabins
Marbella Lane Nohea Stylish Home Makaha
Luxury House (3 Bedrooms) | Terrace/patio

Marbella Lane Nohea Stylish Home Makaha

4.0 star property
Marbella Lane Nohea Stylish Home Makaha
Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760
Sun loungers, beach towels

Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760

9.4 out of 10, Exceptional, (136)
"We walked to Lanikai Beach to go snorkeling."
Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760
Island Jewel — Ocean Front North Shore Paradise
Exterior

Island Jewel — Ocean Front North Shore Paradise

9.6 out of 10, Exceptional, (5)
"It was a fabulous home and the location was perfect! "
Island Jewel — Ocean Front North Shore Paradise
@ Marbella Lane - 3BR w/ Amazing MT & Ocean Vistas
Garden

@ Marbella Lane - 3BR w/ Amazing MT & Ocean Vistas

3.0 star property
@ Marbella Lane - 3BR w/ Amazing MT & Ocean Vistas
Mauna View by Avantstay 10min to Beach, Backyard
House (3 Bedrooms) | Interior

Mauna View by Avantstay 10min to Beach, Backyard

3.0 star property
8.0 out of 10, Very Good, (2)
"We had a wonderful stay. Property was as pictured. The biggest challenges we found is that the area you need to drive through to get to the property is very run down. The property is about a 30 min drive from any safe amenity such as a grocery, gas station etc. If you want to just stay in one place your whole trip this is the place. But if you want to explore around it is not. I would have liked the property to have also listed that there were things like - washer and dryer, hair dryer, general...
Mauna View by Avantstay 10min to Beach, Backyard
@marbella Lane - Elegant 3BR w/ Marvelous Views
Property grounds

@marbella Lane - Elegant 3BR w/ Marvelous Views

3.0 star property
10.0 out of 10, Exceptional, (1)
"This is a pretty new house that is located up in Mākaha Valley. It has a beautiful view of the mountains above the valley. It is only a short drive down to the local surfing beach as well as other local beaches. Our party of six was very comfortable here. "
@marbella Lane - Elegant 3BR w/ Marvelous Views
Studio Nene by AvantStay | Chic, Cozy, King Bed
House (1 Bedroom) | Interior

Studio Nene by AvantStay | Chic, Cozy, King Bed

3.0 star property
Studio Nene by AvantStay | Chic, Cozy, King Bed
'olu'olu by Avantstay Single-story Home by Ocean
House (3 Bedrooms) | Interior

'olu'olu by Avantstay Single-story Home by Ocean

3.0 star property
'olu'olu by Avantstay Single-story Home by Ocean
Alaula by Avantstay Gated Security Home w Valley, Ocean Views!
House (4 Bedrooms) | Front of property

Alaula by Avantstay Gated Security Home w Valley, Ocean Views!

3.0 star property
Alaula by Avantstay Gated Security Home w Valley, Ocean Views!
Cottage Nene by Avantstay Mountain View + Garden
House (3 Bedrooms) | Front of property

Cottage Nene by Avantstay Mountain View + Garden

3.0 star property
Cottage Nene by Avantstay Mountain View + Garden
@ Marbella Lane - Stunning Gem w/ MT & Ocean Views
Terrace/patio

@ Marbella Lane - Stunning Gem w/ MT & Ocean Views

9.0 out of 10, Wonderful, (14)
"It was a beautiful, quiet, peaceful place to stay, we visited the busier areas of the island but enjoyed coming back to the quiet the most. The wildlife you get to see and hear was spectacular!"
@ Marbella Lane - Stunning Gem w/ MT & Ocean Views
Newly Renovated Lanikai, steps to Ocean A/C, kayak, Detached Private cottage
Beach

Newly Renovated Lanikai, steps to Ocean A/C, kayak, Detached Private cottage

3.0 star property
9.8 out of 10, Exceptional, (77)
"Absolutely incredible, couldn’t have asked for a more perfect place to experience the beauty of Kailua & Lanikai. Highly recommend and plan on coming back in the future!"
Newly Renovated Lanikai, steps to Ocean A/C, kayak, Detached Private cottage
@ Marbella Lane - Serene & Lovely MT + Ocean Views
Aerial view

@ Marbella Lane - Serene & Lovely MT + Ocean Views

3.0 star property
@ Marbella Lane - Serene & Lovely MT + Ocean Views
@ Marbella Lane - Stylish House + Impressive Views
View from property

@ Marbella Lane - Stylish House + Impressive Views

3.0 star property
@ Marbella Lane - Stylish House + Impressive Views
@ Marbella Lane - Pōmaika'i Ocean Love Paradise
Terrace/patio

@ Marbella Lane - Pōmaika'i Ocean Love Paradise

3.0 star property
@ Marbella Lane - Pōmaika'i Ocean Love Paradise
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windward Coast Hotel Reviews

OUTRIGGER Reef Waikiki Beach Resort

OUTRIGGER Reef Waikiki Beach Resort

10/10 Excellent
"Frontdesk was very good. ambrose I think is his name."
Alexander 3-night trip
Posted 13 hours ago
OUTRIGGER Reef Waikiki Beach Resort

Frequently asked questions

Why book your cottage in Windward Coast with Expedia?
Expedia has some terrific cottages in Windward Coast, so get set for an unforgettable stay on nature's doorstep. If you have a certain budget, choose how much you'd like to spend and the star rating of your property. Or, make use of our filters to search for cottages with a pool or free WiFi. We'll help you find the right place whatever your bank balance or plans.
How can I find cheap cottages in Windward Coast?
With Expedia's convenient filter tool, booking cheap cottages in Windward Coast couldn't be easier. To discover accommodations that are friendly on the wallet, refine your search by star rating, amenities and budget.