A white gate, a stone wall, and a pink building.

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Oct 1 - Oct 2
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Our top choices for Upper Prince's Quarter hotels

A resort pool area with a curved design, lounge chairs, umbrellas, and a building with a light-colored facade.
A modern living room with a glass coffee table, a beige sofa, a black leather sofa, and a view of a mountainous landscape through large windows.
A coastal hotel with multiple buildings, a dock, and a mountainous backdrop.
A dining table set for six with a bottle of wine, surrounded by wicker chairs, overlooking a body of water and a mountainous landscape.

1. Oyster Bay Beach Resort

Oyster Bay Beach Resort
Oyster Pond
United States
Marv
CA $234
CA $281 total
includes taxes & fees
Oct 4 - Oct 5
Oyster Bay Beach Resort
A clear blue pool with a white deck and palm trees, surrounded by a white fence and buildings in the background.
A marina with numerous boats docked, surrounded by buildings and greenery.
A modern kitchen with stainless steel appliances, a granite countertop, and potted plants on the shelves.
A dining table with breakfast items, a view of the ocean, and a balcony railing.

2. Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
United States
Jason
CA $265
CA $318 total
includes taxes & fees
Oct 3 - Oct 4
Princess Heights Luxury Boutique Condo Hotel
A pool area with lounge chairs and umbrellas, surrounded by palm trees, and a view of the sea.
A coastal resort with a beachfront, multiple hotel buildings, and a swimming pool area.
A balcony with two wooden chairs and a small table, overlooking a beach and ocean.
A beachside resort with striped blue and white umbrellas, lounge chairs, and a clear view of the ocean.

3. JW Marriott St. Maarten Beach Resort & Spa

JW Marriott St. Maarten Beach Resort & Spa
Oyster Pond
United States
Aeryn
CA $441
CA $579 total
includes taxes & fees
Oct 3 - Oct 4
JW Marriott St. Maarten Beach Resort & Spa
A large swimming pool surrounded by palm trees and lounge chairs, with a hotel building in the background.
A hotel room with a large bed, a nightstand, a lamp, and a view of the ocean through a window.
A spacious living room with a sofa, armchairs, a coffee table, and a view of the ocean through large sliding doors.
Two wooden beach chairs with striped towels on a sandy beach with a view of the sea and a small island in the background.

4. Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten
Oyster Pond
United States
Gavin
CA $895
CA $1,074 total
includes taxes & fees
Oct 6 - Oct 7
Dawn Beach Club Resort Sint Maarten
A coastal marina with numerous boats docked, a small island with buildings, and a clear view of the sea.
A beach with white sand and clear blue water. There are palm trees and a volleyball net visible.
A multi-story hotel with a pool, set against a mountainous backdrop.
A kitchen with dark wooden cabinets, a granite countertop, a built-in microwave, and a central island with bar stools.

5. Singh Luxury Apartments With sea View, Apt.1

Singh Luxury Apartments With sea View, Apt.1
Oyster Pond
CA $459
CA $589 total
includes taxes & fees
Oct 3 - Oct 4
Singh Luxury Apartments With sea View, Apt.1
A coastal marina with numerous boats docked, a small island with buildings, and a clear view of the ocean.
A beach with white sand and clear blue water. There are palm trees and a volleyball net visible.
A multi-story hotel with a pool, set against a mountainous backdrop.
A rectangular swimming pool with a tiled edge, surrounded by a wooden deck.

6. Singh Luxury Apartments With sea View, Apt.3

Singh Luxury Apartments With sea View, Apt.3
Oyster Pond
CA $1,011
CA $1,168 total
includes taxes & fees
Oct 3 - Oct 4
Singh Luxury Apartments With sea View, Apt.3
A multi-story building with a pool, surrounded by hilly terrain.
A modern living room with a glass coffee table, a red vase, and a grey armchair.
A hotel entrance with a yellow facade, a paved walkway, and various plants and flowers.
A kitchen with dark wooden cabinets, a granite countertop, a built-in microwave, and a central island with bar stools.

7. Singh Luxury Apartments With sea View, Apt.2

Singh Luxury Apartments With sea View, Apt.2
Oyster Pond
CA $459
CA $589 total
includes taxes & fees
Oct 3 - Oct 4
Singh Luxury Apartments With sea View, Apt.2
A beachside lounge with lounge chairs and umbrellas, overlooking the sea.
A balcony with a view of a beach and ocean.
A Holland House Beach Hotel reception area with a wooden deck, potted plants, and a signboard.
A person relaxing on a beach chair with a drink, overlooking a clear blue sea and a distant shoreline.

8. Holland House Beach Hotel

Holland House Beach Hotel
Downtown Philipsburg
United States
James
CA $323
CA $387 total
includes taxes & fees
Oct 4 - Oct 5
Holland House Beach Hotel
A pool area with lounge chairs, palm trees, and a view of the ocean.
A resort with beachfront villas, a pier, and clear turquoise waters.
A modern hotel dining area with a buffet, seating arrangements, and a glass partition.
A spacious lounge area with a large window overlooking the sea, featuring a modern sofa set, a round coffee table, and a decorative vase.

9. Oceans at Divi Little Bay

Oceans at Divi Little Bay
Philipsburg
United States
Marc
CA $275
CA $360 total
includes taxes & fees
Oct 30 - Oct 31
Oceans at Divi Little Bay
A beach with a clear view of the ocean, a sandy shore, and a mountainous backdrop.
A view of a coastal area with a large ship in the water, a small boat, and a building with a red roof.
A hotel room with a dining area, kitchenette, and a sofa.
A room with a sofa, a glass table with a bottle, curtains, a TV, and a view of the ocean.

10. Horizon View Beach Hotel

Horizon View Beach Hotel
Downtown Philipsburg
United States
Chris De
CA $127
CA $152 total
includes taxes & fees
Oct 3 - Oct 4
Horizon View Beach Hotel
A view from inside a building looking out to a beach with clear turquoise water and a distant ship.
A hotel room with two beds, a television, a small table, and a door leading to a balcony.
A modern living room with a grey sofa, a small dining table, and a refrigerator.
A hotel room with a bed, a nightstand, a potted plant, a painting, and a view of the sea.

11. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
Downtown Philipsburg
United States
Yollanda
CA $94
CA $115 total
includes taxes & fees
Oct 15 - Oct 16
MIDTOWN MOTEL SXM
A neatly made bed with a red bedspread, two matching lamps on either side, and a colorful pillow on the headboard.
A beige armchair in a room with a white wall, an exit sign, a framed picture, and two potted plants.
Alicia's Inn Guest House with a sign for Victor's Cosmetics.
A corridor with red and white walls, a fire exit sign, and barred windows.

12. Alicia's Inn

Alicia's Inn
Downtown Philipsburg
United States
Shelda
CA $109
CA $141 total
includes taxes & fees
Oct 6 - Oct 7
Alicia's Inn
A hotel room with a bed, a sofa, a small round table, and a chair. There is a bathroom visible through an open door.
A hotel room with a bed, a sofa, a rug, and a patterned wall.
A spacious lobby with a reception desk, seating area with sofas and chairs, a coffee machine, and a refrigerator.
A modern dining area with a mix of yellow and green chairs, a central table, and a ceiling with wooden panels and hanging lights.

13. July Apartments

July Apartments
Madame's Estate
United States
JoyAnn Carolyn
CA $132
CA $138 total
includes taxes & fees
Oct 11 - Oct 12
July Apartments
An aerial view of a beach resort with rows of sun loungers and umbrellas, a pool, and a building with a blue facade.
A restaurant with wooden tables and chairs, a bar area, and large windows with a view of the outdoors.
A spacious living room with a large window overlooking a tropical garden and the ocean. There are two sofas, a coffee table, and a TV on a stand.
A pool area with a waterfall feature, surrounded by wooden deck chairs and covered seating areas.

14. Belair Beach Hotel

Belair Beach Hotel
Belair
Canada
Roman
CA $227
CA $274 total
includes taxes & fees
Nov 2 - Nov 3
Belair Beach Hotel
A covered balcony with a view of the ocean, a wicker chair, and a green door.
A bar area with a counter, stools, and a variety of bottles.
A hotel room with a four-poster bed, a television on a wooden dresser, and a nightstand with a coffee maker.
A pool area with lounge chairs, a pergola, and a view of the ocean.

15. Island Heights

Island Heights
Orient Bay
CA $355
CA $372 total
includes taxes & fees
Oct 15 - Oct 16
Island Heights
A swimming pool with a red roof, surrounded by potted plants and a white fence.
A spacious living area with a red sofa, wooden chairs, a coffee table, and various potted plants.
A spacious indoor area with wicker furniture, a television, and potted plants.
A stone-paved courtyard with potted plants and a building with a red roof.

16. L'Esperance Hotel

L'Esperance Hotel
Philipsburg
United States
Linda
CA $175
CA $204 total
includes taxes & fees
Nov 1 - Nov 2
L'Esperance Hotel
A beach view from a covered area with palm trees and a clear blue sea.
A swimming pool with tiled edges, surrounded by tropical vegetation and a building labeled "Departure Lounge".
A beachfront hotel with a sandy beach, palm trees, and a pool area.
A spacious kitchen with a dining area, a large mirror, and a view of the outside.

17. Mary's Boon Beach Resort & Spa

Mary's Boon Beach Resort & Spa
Simpson Bay
United States
Virginia
CA $178
CA $213 total
includes taxes & fees
Oct 4 - Oct 5
Mary's Boon Beach Resort & Spa
A circular window view of a beach with a swimming pool, palm trees, and a sandy area with umbrellas.
A view through a window with tropical curtains, revealing a beach with umbrellas and lounge chairs.
A deck with lounge chairs and tables overlooking a marina and mountains.
A beach scene with a sign that reads "WE LOVE St. Maarten" and a view of boats in the background.

18. Seaview Beach Hotel

Seaview Beach Hotel
Downtown Philipsburg
United States
Anastasia
CA $114
CA $141 total
includes taxes & fees
Nov 1 - Nov 2
Seaview Beach Hotel
A resort pool with lounge chairs, palm trees, and a view of the ocean.
A coastal resort with multiple buildings featuring red roofs, a rocky shoreline, and a clear view of the sea.
A coastal hotel with multiple red-roofed buildings, a beach, and a cruise ship in the background.
A hotel lobby with multiple seating areas, a central bar, and a kitchen visible in the background.

19. Divi Little Bay Beach Resort

Divi Little Bay Beach Resort
Philipsburg
United States
Chad
CA $241
CA $314 total
includes taxes & fees
Oct 3 - Oct 4
Divi Little Bay Beach Resort
A beach with rows of sun loungers and umbrellas, a building with balconies, and a backdrop of dense green foliage.
A living room with a ceiling fan, a sofa, a coffee table, and a dining area with chairs.
A beach view with a palm tree, a wooden fence, and a chair.
A bedroom with a four-poster bed, a bedside table with a lamp, a wooden bench, a desk with a chair, and a wardrobe.

20. The Crown House Hotel

The Crown House Hotel
Downtown Philipsburg
United States
Monique
CA $118
CA $141 total
includes taxes & fees
Oct 4 - Oct 5
The Crown House Hotel
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Stay near popular Upper Prince's Quarter attractions

Guana Bay Beach

9.0/10 (92 reviews)
The picturesque shores of this tranquil bay provide a great opportunity to escape the crowds and jump in the crystal clear water for surfing or swimming.
See properties

Port of St. Maarten

Explore the waterfront in Philipsburg with a trip to Port of St. Maarten.
See properties

Gibb's Bay Beach

8.0/10 (27 reviews)
Why not spend a lazy afternoon at Gibb's Bay Beach during your trip to Upper Prince's Quarter?
See properties

Learn more about Upper Prince's Quarter

Head to sights like Dawn Beach and Guana Bay Beach as you discover Upper Prince's Quarter.

See all hotels in Upper Prince's Quarter
A beach with clear turquoise waters, a sandy shore, and houses on a hillside.

Top Upper Prince's Quarter Hotel Reviews

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

10/10 Excellent
"Last year we stayed at Little Debbland we had an ocean view"
Gabreille Lynn 6-night trip
Posted 7 hours ago
Divi Little Bay Beach Resort
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

10/10 Excellent
"Amazing breakfast. The Air conditioning was awesome."
Milanneris 3-night trip
Posted 9 hours ago
The Villas at Simpson Bay Resort
Oyster Bay Beach Resort

Oyster Bay Beach Resort

8/10 Good
"Beach was nice. A lot of seaweed. But it’s cleaned daily. The main restaurant was low on choices. The beach bar is much better for food. Very nice staff."
Clare 4-night trip
Posted 1 day ago
Oyster Bay Beach Resort
JW Marriott St. Maarten Beach Resort & Spa

JW Marriott St. Maarten Beach Resort & Spa

10/10 Excellent
"Everything was wonderful, I would stay there again! The staff is amazing- all of them!"
Danielly 3-night trip
Posted 2 days ago
JW Marriott St. Maarten Beach Resort & Spa
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

8/10 Good
"We enjoyed our stay. Only issue was the bathroom. There was not enough lighting. A little update bathroom tile was needed."
Anita Lynne 4-night trip
Posted 3 days ago
Sonesta Ocean Point All Inclusive, Adults Only Resort
Villa Angelina with Amazing Panoramic Views. Enjoy the quiet at Oyster Pond

Villa Angelina with Amazing Panoramic Views. Enjoy the quiet at Oyster Pond

8/10 Good
"The view was definitely the showstopper. You could not beat the views of the Oyster Bay, the Atlantic Ocean, St. Barth to the east and Anguilla to the north.The inside of the house was clean but needed to be updated. Beds were comfortable and they had all the essentials for the house.The location was great. It was in a quiet neighborhood.And let's face it, Saint Maarten is not that big so you could drive from one point of the island to the other in about 20 to 30 minutes, depending on traffic.We were disappointed upon arrival, how the outside of the property looked. It looked like no one had clean the patio, area where the grill was or the pool area in anticipation of our arrival. There were broken chairs from the patio set laying out.I got up the next morning and washed off those areas myself so that we could use them without feeling like we was stepping in dirty areas. I say all of this the say, the view made up for all of this. I think the property was recently bought, so I just think it needs a little work and they would have a gem on their hands.If you ask, what I stay there again? I would.The view!!"
kevin h. 7-night trip
Posted 4 days ago
Villa Angelina with Amazing Panoramic Views. Enjoy the quiet at Oyster Pond
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

10/10 Excellent
"I a wonderful stay! The place was clean, comfortable, and exactly as described. The location was convenient, and everything we needed was provided. The host was friendly, responsive, and made the whole experience easy and enjoyable. We really appreciated the attention to detail and would definitely stay here again. Highly recommend!"
Pearlene 3-night trip
Posted 8 days ago
Panorama Residences at Monte Vista
FantaSea beachfront, every bedroom facing ocean! Remodeled 2024

FantaSea beachfront, every bedroom facing ocean! Remodeled 2024

10/10 Excellent
"Beautiful stay!"
Yermina W. 6-night trip
Posted 1 month ago
FantaSea beachfront, every bedroom facing ocean! Remodeled 2024
LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site

LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site

10/10 Excellent
"This was an excellent property and was exactly as advertised. Beautiful villa, very roomy and comfortable. We did not rent a car and used a taxi for the week. The expense was about the same and this way we didn’t have to drive. Communication with everyone was so easy and pleasant. We didn’t get to access the ocean because the sargassum was very heavy but they removed as much as they could every morning and there was never an unpleasant smell. By the end of the week, the winds had changed and kept the seaweed to a minimum. My family really enjoyed the quiet area of Oyster Bay/Dawn Beach and the space of the villa for a family of six. Overall, we had an excellent time and enjoyed our stay!!"
Shannon W. 7-night trip
Posted 2 months ago
LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site

More cheap stays in Upper Prince's Quarter

Adonis Cupecoy

Adonis Cupecoy

Jordan Road Lowlands
CA $105
CA $111 total
Oct 5 - Oct 6
includes taxes & fees
7.2/10 Good! (541 reviews)
Adonis Cupecoy
MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM

Kruythoffsteeg#10 Philipsburg
CA $94
CA $115 total
Oct 15 - Oct 16
includes taxes & fees
7.4/10 Good! (73 reviews)
MIDTOWN MOTEL SXM
Alicia's Inn

Alicia's Inn

Backstreet 42 Philipsburg
CA $109
CA $141 total
Oct 6 - Oct 7
includes taxes & fees
8.8/10 Excellent! (352 reviews)
Alicia's Inn
Carls Unique Inn

Carls Unique Inn

18 Orange Grove Rd Cole Bay
CA $131
CA $159 total
Oct 29 - Oct 30
includes taxes & fees
8.6/10 Excellent! (449 reviews)
Carls Unique Inn
L'Esperance Hotel

L'Esperance Hotel

4 Tiger Road Philipsburg
CA $175
CA $204 total
Nov 1 - Nov 2
includes taxes & fees
8.4/10 Very good! (154 reviews)
L'Esperance Hotel
Cocovaa

Cocovaa

34 white sands rd Simpson Bay
CA $174
CA $209 total
Oct 11 - Oct 12
includes taxes & fees
Cocovaa

Frequently asked questions

When is the best time to go to Upper Prince'S Quarter?
The best time to go to Upper Prince's Quarter is during the dry season, which runs from December to May, offering consistently pleasant weather.During these months, you can expect plenty of sunshine and comfortable temperatures, typically ranging from 24°C to 30°C. This period is ideal for enjoying the outdoor activities and natural beauty of the area, like exploring the local beaches or taking boat trips. The lower humidity also makes for a more enjoyable experience overall.For travellers looking for a more relaxed and less crowded experience, the shoulder months of May and early June can be a good option.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Upper Prince's Quarter.
How much is the nightly rate at a Upper Prince's Quarter hotel?
Prices for hotels in Upper Prince's Quarter often vary, but you can find a great deal from CA $111 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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