Compare Simpson Bay Cottage Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Hotel Options in Simpson Bay

    The Morgan Resort Spa Village

    The Morgan Resort Spa Village

    2 Beacon Hill Road Simpson Bay
    $394 nightly
    The price is $411 total per night from Jan 7 to Jan 8
    $411 total
    Jan 7 - Jan 8, 2026
    Total with taxes and fees
    8.8/10 Excellent! (1,909 reviews)
    Simpson Bay Resort, Marina & Spa

    Simpson Bay Resort, Marina & Spa

    Billy Folly Road 37 Simpson Bay
    $332 nightly
    The price is $346 total per night from Jan 25 to Jan 26
    $346 total
    Jan 25 - Jan 26, 2026
    Total with taxes and fees
    8.8/10 Excellent! (1,540 reviews)
    Hilton Vacation Club Flamingo Beach St. Maarten

    Hilton Vacation Club Flamingo Beach St. Maarten

    Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
    $360 nightly
    The price is $378 total per night from Jan 15 to Jan 16
    $378 total
    Jan 15 - Jan 16, 2026
    Total with taxes and fees
    9/10 Wonderful! (1,378 reviews)

Cottages

Book a cottage in Simpson Bay
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Simpson Bay. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Simpson Bay better.

Cottage apartments in Simpson Bay range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Simpson Bay
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Simpson Bay and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Simpson Bay cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Simpson Bay. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Simpson Bay Cottages essential information

Accommodation
Cottages
Lowest Price
$346
Highest Price
$411
Popular accommodation
The Morgan Resort Spa Village, Simpson Bay Resort, Marina & Spa, Hilton Vacation Club Flamingo Beach St. Maarten