The Chester Hotel

10/10

Exceptional

26 Jun 2026

Kaitlyn

Our family enjoyed our stay at Simpson Bay Resort. The 2-bedroom condo fit our family of six nicely - two murphy beds in the living room were a nice surprise. There were a ton of pools and my kids were able to swim laps in the morning. The beach was nice (not the best on the island) and we liked walking along the water and iguana watching. It was a short walk to town where we grabbed dinner a couple of times. Don't miss Topper's Ice Cream.

Friends_and_family Family

10/10

Exceptional

26 Jun 2026

William

Absolutely nothing to complain about. We had a wonderful 8 days, enjoyed the beach, the bar, the restaurants, and did an excursion with the in house tour company Aqua Mania. All provided top notch service and quality.

Friends_and_family Friends

10/10

Exceptional

25 Jun 2026

Jennifer

Beach area was great. The pool closest to our room was beautiful and the bartender at the swim up bar was fantastic. Great choices for different places to eat

Family

10/10

Exceptional

25 Jun 2026

turry

Staff was very friendly & the ro was very clean & spacious

Partner

8/10

Excellent

25 Jun 2026

Kevin

Positives: Beautiful property. Good food options if you have breakfast included in your package. Lovely pools. Good customer service.

Negatives: the bus shuttle was never readily available to take me from my room to the check-in counter or for breakfast. The property is big so the shuttle service should be improved. My air-conditioning was faulty and often times I had to call maintenance to fix it.

Family_with_children

10/10

Exceptional

25 Jun 2026

Jimmy

It was nice but there were ants in our room. However it didnt affect the quality of our stay

Friends

8/10

Excellent

24 Jun 2026

Alphanso F

Clean room

Self

10/10

Exceptional

24 Jun 2026

Nequita

Very friendly staff and in a great location to walk to all the restaurants and bars on the strip

8/10

Excellent

24 Jun 2026

Mario

Just there for one night &’it was a good experience

Partner

10/10

Exceptional

23 Jun 2026

Cynthia

The villa was amazing and exceeded our expectations! There was so much room for everyone!

Family_with_children

10/10

Exceptional

23 Jun 2026

Edwin F

Amazing Staff we had a great time

Partner

10/10

Exceptional

23 Jun 2026

Marcella

Was great last minute booking. We forgot chargers and toothbrushes so if they had some available that would have made it better but overall it was a great check in experience

Partner

10/10

Exceptional

22 Jun 2026

Gino

The staff was very helpful and very approachable, so don’t hesitate to ask questions, they are more than happy to help!

Self

8/10

Excellent

21 Jun 2026

Alexis

resort what’s clean and staff were nice. We were a little confused on how to get around the property and when we finally figured out, there was a shuttle and you would’ve called the shuttle would not come so that was a really big inconvenience as I stated before the resort is big and on hills but that location of this resort is a 10 out of 10 so I would stay here again.

Partner

8/10

Excellent

21 Jun 2026

Miclyne

This was the 2nd time I stayed at the resort. I love the rooms and the resort.
The only thing is that there's not much activities on the resort. It's a huge property but no information given to the guests regarding what activities are happening on the resort. Also, alot more on one side of the resort is happening but without no information being provided. Overall, the staffs are excellent. The Housekeepers work very hard. The rooms are well kept.

Partner

10/10

Exceptional

21 Jun 2026

German

Clean room, nice restaurants within walking distance.

Family_with_children

8/10

Excellent

20 Jun 2026

Kimberley

Clean beaches. Quiet, beautiful view of the Marina, quick access to/from the airport.
Laura @ the Marina pool bar was always so cheerful, friendly and amazing at her job!
Nanya in Housekeeping kept our suite very clean.
The check-in was slow & frustrating.
Bovin Steak House was overpriced. service/food was not up to expectations for the price.
My steak was well-done instead of medium-rare & so my wife was done her dinner before my replacement came out.
Neither the Chef nor the Manager came out or offered anything for our dinner.
We found the small grocer on site had any extras we needed and were very nice.
Would stay again and would definitely stay in the same suite.

Partner

8/10

Excellent

19 Jun 2026

Emily

The property is huge and situated in a lovely area right on the bay. The only thing that is frustrating is how long and slow the check in process is. Both times I’ve stayed, I had to sit in the lobby waiting for multiple people to verify that the room was ready. Seems like they really ought to have a better system than the front desk sending the concierge who then sends the valet to physically drive over. Either housekeeping turned the room or they didn’t. Should be something verifiable by computer or a radio check. Not 30-40 minutes of sitting around the lobby waiting. Otherwise, I thoroughly enjoyed my time there.

Self

10/10

Exceptional

18 Jun 2026

raudel

Limpieza restaurante piscina playa

10/10

Exceptional

18 Jun 2026

Jodi

Simpson bay was amazing like a little town
My room was up a hill from
The ocean. But there are shuttles. I will be going back for sure.

Family_with_children

4/10

Poor

18 Jun 2026

thomas

Staff was poor at beach bar. Ignored customers same at breakfast. Had to beg for coffee refill. Steak house service was excellent. Isaiah was 5 star only good thing there

Family

6/10

Pleasant

16 Jun 2026

Gilson

It’s an OK property, dated rooms and very inconvenient 10 am check out with a little or no flexibility.

Self

8/10

Excellent

16 Jun 2026

Christopher

The classification of the rooms were a bit misleading and could have caused issues on my vacation. I reserved a studio suite however the pictures shown did not reflect what I got when I arrived. However, I was able to find a more suitable option after some negotiations with the management. I had to pay for said option though.

Partner

8/10

Excellent

16 Jun 2026

Robert

Need an Italian restaurant on site

Partner

10/10

Exceptional

16 Jun 2026

Rebecca

This hotel was better than expected. The rooms were super clean, and that is a pet peeve of mine. Staff was very friendly and approachable. Lots to do in the area in a ton of different restaurants on site and in walkable distance.
I will definitely be back for a longer stay.

Self

10/10

Exceptional

15 Jun 2026

Stephany

Great staff, our housekeepers were diligent with their daily cleaning. We enjoyed the place. The beach was beautiful. Thank you!

Family_with_children

4/10

Poor

14 Jun 2026

Deborah

The Murphy bed was uncomfortable it caused back ache pains. The airco in the living room wasn't working it ws hot we called maintenance he tried however it was not fixable in the night he said we had to wait until morning and we were already schedules to check out so that did not go well from the first night we encounter hot living room we thought it would be cool by evening and it wss too late to call to fix it. The tv had another issue the eminence person was abke ti fix that. The building ws very hard fo find there should be cleared signs to locate the room

Family_with_children

10/10

Exceptional

13 Jun 2026

Shyane

Sooo pretty!! I loved it and the staff are sooo nice and helpful. They will give you rides around the hotel and get you close to the strip. Everything we wanted to do was walking distance

Friends

6/10

Pleasant

13 Jun 2026

felicia

I didn’t like the food .

Friends

10/10

Exceptional

12 Jun 2026

armand

Many different restaurants in sure the beach was lovely. Staff is so friendly and willing to help.

Family

10/10

Exceptional

12 Jun 2026

Roger

We had an amazing time. Facilities were great, location was amazing, food was good, and everything you need is right there.

Family_with_children

6/10

Pleasant

11 Jun 2026

Maria

Good location

Friends

8/10

Excellent

10 Jun 2026

Brittany

Very helpful and accommodating staff. Lovely resort!

Friends

10/10

Exceptional

08 Jun 2026

Brian

Great pools. Great beach. Great restaurants.

Family

10/10

Exceptional

08 Jun 2026

William

Very friendly staff and an outstanding facility

Partner

10/10

Exceptional

05 Jun 2026

Lesley Ann

This is a beautiful property. We will be back.

Partner

6/10

Pleasant

05 Jun 2026

Sylvana

Overall, our stay was okay, but a few things took away from the experience. The view was nice, and the property is in a lively area within walking distance of many restaurants and bakeries. However, the staff wasn’t very friendly. The room was clean, but one day after housekeeping finished, the room smelled strongly of weed. Also, you have to pick up and return beach towels yourself at the pool or beach, they don’t bring them to the room and even refused to take them back after we used them.

Family

6/10

Pleasant

05 Jun 2026

Taniel

Decent stay.

Cons-
Rooms very outdated. Flushing the toilet will wake the entire room. Noisy drainage and piping - random mechanical noises early in the AM. Far from the hotel lobby and other amenities. I would rather stay in the Villas at Simpson Bay Resort than on this side.

Pros- housekeeping does a great job.

Friends_and_family Family

4/10

Poor

05 Jun 2026

carol

The responses to inquiries for help was abysmal

Self

8/10

Excellent

04 Jun 2026

Stacy A.

Perfect location. Beautiful ocean area. No seaweed. Lots to do right on site. Room was a big worn down and bathroom way too small. The room itself brought my review down, but the location and all the pools were great. Also, the employees were not very friendly.

Partner

6/10

Pleasant

03 Jun 2026

TANU

Overall a great resort but the rooms are not upgraded for the ratings it has. We would likely not book again. The staff was very friendly and convenient to have the supermarket and a couple of restaurants for quick bites nearby.

Family_with_children

10/10

Exceptional

03 Jun 2026

Vernetta

Always an amazing time at Simpson Bay!!

8/10

Excellent

03 Jun 2026

Sarita V

clean room and friendly saff

Self

4/10

Poor

02 Jun 2026

Deri

Staff was amazing and kind for most part but WiFi was trash and my room ac didn’t work and shower leaked. Maintenance didn’t really help with anything and I had to call IT multiple times to get them to help with WiFi

Family

10/10

Exceptional

31 May 2026

Vanessa

Amazing

Self

10/10

Exceptional

30 May 2026

Elna Marie

Hotel is basically a subdivision with its own convenience store and multiple restaurants. Hotel is in prime location with nearby restaurants, shopping, entertainment and excursions that’s within walking distance. Room layout is more apartment than hotel.

Cons:
Concierge/activity staff were not helpful. They give you an envelope of useful excursions, hotel activities and information, but does not assist in booking. You have to do it yourself or find other alternatives as some activity brochure was out of date.

Friends

8/10

Excellent

30 May 2026

Marsha

Had to call the front desk for housekeeping assistance a couple times, as all rooms were not attended to...staff was helpful ...beach views were gorgeous...breakfast was always perfect

Friends

10/10

Exceptional

30 May 2026

Courtney

Great place to stay in Sint Marteen.

I recommend the front desk ask all guest if they had activities planned or make a few suggestions. They should also provide directions to the restaurants on the property, we had to figure it out ourselves.

I also suggest you put teas and coffees in the room.

Check out La Petrona for the buffet breakfast. Ask for Kayla

Check out Bovine steakhouse for dinner and ask for Dania.

Check out Aquamania Adventures for your sunset or dinner cruises.

See you soon

Friends_and_family Family

10/10

Exceptional

29 May 2026

Linda

Had an ocean view room and a beautiful view. Room was very nice. Some restaurants on site and several within walking distance. Housekeeping was excellent. Pools were nice. Would stay again.

Partner

10/10

Exceptional

28 May 2026

Timothy

I had a great stay at this hotel from start to finish. The staff was welcoming, professional, and always willing to help with anything I needed. The room was very clean, comfortable, and well-maintained, with a nice view and plenty of space to relax.

Partner

10/10

Exceptional

28 May 2026

Stephanie

It was perfect

Family

10/10

Exceptional

28 May 2026

Kijana

Staff was great

10/10

Exceptional

27 May 2026

April

Room were really clean everyday

Family_with_children

10/10

Exceptional

27 May 2026

Wendy

The beach was clean and appreciate the lounge chairs are included for free.
The only complaint I have is the lack of on site entertainment or music. We really expected that their would be island music played at the pool, or music at some of the restaurants. Music would draw more business into the restaurants, and the area. It was pretty dead at the resort . Didnt see many people there other than when waiting for the Sunset cruises.

Partner

10/10

Exceptional

27 May 2026

Kathleen

Room was clean. Was disappointed that our room with a \"balcony\" was still ground level. Security staff was great. Reception staff could have been a little nicer. Beach view was good. Very nice resort. Would stay again.

Partner

10/10

Exceptional

27 May 2026

blanca

beach

10/10

Exceptional

25 May 2026

Ruben

Simpson Bay Resort is a great place to stayt, the breakfast buffet is very good, we recommend that you include it in your reservation. The beaches are beautiful, comfortable to swing. The pools are very clean and warm. Overal, we liked it and we would stay here again in our next trip to St. Marteen.

Partner

8/10

Excellent

24 May 2026

pat

Good location to town but huge property. Be prepared to walk!

Family

10/10

Exceptional

24 May 2026

james

We booked \"ocean front\" upon arrival we were put in a marina room, which we considered bay and ocean view

8/10

Excellent

24 May 2026

Eugene

Been to St Maarten a few times on a cruise but first time staying for a week..Simpson Bay Resort is a beautiful Resort has everything you would need.the buffet breakfast isn't worth the extra cost,you can easily walk 5 mins down the street to Buccaneer beach bar for breakfast so good and there are more places to eat breakfast close by.if you eat there the beach chairs and umbrella are free.take a tour around the island so you can see all the different beaches restaurants,shops...

10/10

Exceptional

24 May 2026

Sarah-Jane

Everything was great!

Friends

10/10

Exceptional

24 May 2026

Terry c

First time in St. Maarten, and Simpson Bay Resort was incredible. What a wonderful place for a vacation. Big and beautiful, full of resturants, and the beach for amazing. Coco beach bar was worth it everyday with specials and great drinks. We would return here.

Family

8/10

Excellent

23 May 2026

Rebecca

We loved our stay at Simpson Bay. The only reason we are giving four stars is because the wifi doesn’t work and the cell phone service in that area is hit or miss. Makes planning hard when you can’t see what is around

Partner

10/10

Exceptional

21 May 2026

Sherry

The resort is beautiful and quiet. The beach is very small but it’s clean. The restaurants are good. The rooms could be clean better. Some of the staff makes you feel unwanted mainly the housekeeping staff. If the beach was bigger and some entertainment I would definitely return back to the resort.

Partner

10/10

Exceptional

20 May 2026

Jennifer

clean rooms, pool access, and casino. Everything is close by

Partner

8/10

Excellent

19 May 2026

Brian

our room is adjacent to the big pool which is nice and convenient

Partner

10/10

Exceptional

19 May 2026

Aaliyah

So amazing

Self

8/10

Excellent

18 May 2026

Desiree

I truly enjoyed my stay at this resort. The location is incredibly convenient—being so close to everything made it easy to get around on foot and saved us money. The staff played a huge role in making our experience enjoyable, everyone was friendly, welcoming, and kept us entertained throughout our stay. Special shoutout to Ramon, Will, Natasha, Troy, Michael, and others—they were amazing.

Unfortunately, there was one staff member whose behavior did not align with the others. He was an older bald driver with yellow teeth. He made an inappropriate comment about something I cannot change, which left both of us feeling uncomfortable. I don’t recall his name but I’m confident the resort can identify him. I chose not to let this incident overshadow my positive experience but he was extremely rude and completely opposite of his colleagues.

Aside from that experience, we had a great time and truly appreciated the rest of the staff.

Friends

10/10

Exceptional

17 May 2026

Sol Magdalena

Great location. Near good restaurants. Food was amazing. Hotel is quiet, clean and safe. Recommend 10/10.

10/10

Exceptional

17 May 2026

Susan

Entire resort is anazing

Family

10/10

Exceptional

16 May 2026

Sherry

Excellent place to stay!

10/10

Exceptional

16 May 2026

Kristen

Awesome location! Shuttle was easy pickup (don’t forget to tip) many restaurants nearby walking distance
Beach was nice. Room was comfortable and kitchen had everything needed

10/10

Exceptional

16 May 2026

LisaMarie

Great location and amazing beaches! Will definitely be back.

10/10

Exceptional

15 May 2026

Janee

I could not have stayed at a better place! Simpson bay is centrally located to all the businesses. All the businesses will call the shuttle to the meeting point for you. It is quite large but by day two I could navigate by foot and the shuttle service is robust.

The staff were welcoming accommodating nothing felt like a money grab. I generally do not revisit resorts in search of different experiences. But I will be visiting again!

Friends

8/10

Excellent

15 May 2026

mireille

.

Family

10/10

Exceptional

15 May 2026

Marie

I had a view of the marina from my room and had awesome sunset views every day.

Partner

10/10

Exceptional

13 May 2026

zitlhalit

Best resort I’ve stayed in yet ! Only thing I would say is that security should work on being nicer

Family_with_children

8/10

Excellent

13 May 2026

Nimrat Kaur

Perfect place to stay. 100% recommended. It got pool, beach, restaurants, shuttles within the resort area.

Family

10/10

Exceptional

13 May 2026

John

The property was amazing and well kept. Multiple restaurants on site and down from the property made it perfect location and no need for a car. Taxis were readily available at the lobby when we needed to go anywhere. The onsite grocery was great for anything that we needed and was one of the best features of the resort. It had a great selection of alcohol and food items if you wanted to eat in room. Prices were very reasonable and didn't feel like they were taking advantage of the guest at all. Now the best part was the bars. There seem to be a happy hour close to the beach from 1 to 5 at either the Hilton property next door or the beach bar or pool bars so there were no issues getting drinks and lay on beach. The only complaint that I had was we had a room up the hill and the walk was pretty bad for a 60 year old. I would pay the difference and get closer to the beach in the future.

Partner

8/10

Excellent

11 May 2026

mikell

The beach was excellent. The property was old and outdated and could use a better shuttle system. The A/C units in the rooms weren't cooling good enough so the rooms were warm

Partner

8/10

Excellent

11 May 2026

Erik

We loved May at the Coco Bar!

Family

10/10

Exceptional

10 May 2026

Liz

Everyone on the resort was so welcoming and helpful. Would highly recommend

Friends

10/10

Exceptional

10 May 2026

Stephanie

We really enjoyed our week. We bought the breakfast buffet everyday which was awesome. However first timers to St Maarten and the resort, some basics left out, sometimes handing

Partner

10/10

Exceptional

10 May 2026

Richard

Very clean and comfortable.

Self

8/10

Excellent

10 May 2026

Louise

Staff were attentive and night agent was particularly helpful with my early morning check out.
Britt Cafe was useful for the few items I needed for an overnight stay.

Self

10/10

Exceptional

09 May 2026

martha Anne

Great location. Well maintained grounds. Friendly staff.

Partner

10/10

Exceptional

09 May 2026

chantelle

Simpson Bay is the perfect location in SXM. It's walking distance to restaurants, clubs and shopping. I will say make sure you know if you're staying at the villas or condos. There is a difference and you may be walking up hills and not aware, as well as the modern updated rooms or not. The beach is beautiful, staff is friendly, free shuttles are an option when in service, and several pools on-site. My one con is that there is a daily fee to use the gym; I was not happy about that.

Friends_and_family Friends

10/10

Exceptional

09 May 2026

chantelle

Simpson Bay is the perfect location in SXM. It's walking distance to restaurants, clubs and shopping. I will say make sure you know if you're staying at the villas or condos. There is a difference and you may be walking up hills and not aware, as well as the modern updated rooms or not. The beach is beautiful, staff is friendly, free shuttles are an option when in service, and several pools on-site. I will stay here again!

Friends_and_family Friends

10/10

Exceptional

09 May 2026

Michelle

Simpson Bay Resort was superior. They exceeded all my expectations. The place impeccably clean, staff was so friendly and accomdating no matter where we were in the resort. The around the world boat tour on the santino was a lot of fun. We enjoyed the shopping trip to Philipsburg. Lunch and shopping along all the street shops, many designer boutiques. AMA's jewelry store owner RT, she was fabulous! I would recommend highly at trip to Sint Maarten at Simpson Bay Resort.❤️❤️❤️

Partner

10/10

Exceptional

08 May 2026

Morgan

Stayed at the Simpson Bay Resort for our first trip to St. Maarten. It was a great stay! Easy access to popular restaurants and nightlife. Great beach views and access as well. The staff were very helpful and accommodating. Highly recommend, especially for a budget friendly option!

Partner

8/10

Excellent

08 May 2026

Collin

I had a very good stay at Pelican Resort Marina & Spa. The room was comfortable, the property was clean and well maintained, and the overall atmosphere was relaxing. The staff was friendly and helpful throughout my visit, and I had no complaints during my stay. Very nice place to stay, and I would definitely consider coming back again.

Self

10/10

Exceptional

08 May 2026

Javier

Everything was great.
Ammenities, gym had additional cost.

Business

10/10

Exceptional

08 May 2026

Elizabeth

Staff was extremely nice and helpful. The food was good

Family_with_children

8/10

Excellent

07 May 2026

Monicka Shnay

Room was spacious but once the Murphy bed is down its a task. But the toliet flush is loud as ever. It also had a sewer smell the whole trip in bathroom after we showered. The beds are comfortable and the shower is good pressure. Some staff was so rude. But front desk staff wqa nice.

Friends

10/10

Exceptional

06 May 2026

Vivian

Our condo was ready even though we were early arrivals. The bellman transported us and our gear to the condo, he verified that all keys worked properly before leaving.
The housekeeping manager was just finishing her inspection when we arrived. The unit was clean, supplies plentiful, and everything worked as it should. Bonus, there was an ice maker in the fridge with the bin half full of cubes already.
All staff on site were pleasant, polite and helpful during our stay. We will definitely be back, and promote it with family and friends

Friends_and_family Friends

10/10

Exceptional

06 May 2026

Jomo

The resort was a lot better than I expected. The staff was amazing and the room was comfortable

Self

10/10

Exceptional

06 May 2026

Madhu

We had a great stay @ Simpson Bay! From the moment we checked-in, staff was very friendly and accommodated our room request; we had spacious room that was very well-maintained and had beautiful view of the bay. Room service was fairly quick on a few occasions and delicious. In addition to the restaurants on-site, there is a grocery store just outside the resort and overflowing amount of great cafes and restaurants. Well-worth the stay!

Family_with_children

10/10

Exceptional

05 May 2026

marae

Visited Sint-Marteen for the first time for my friend's 40th birthday. Love that this resort was pretty central. Close to restaurants, casinos, rhum tasting etc.

Staff friendly and helpful. Shuttle service was great. Felt safe. We had breakfast included and it was delicious. Beautiful views. Will stay again but in a room with a view.

Friends

10/10

Exceptional

05 May 2026

bill

beautiful large suite with nice view

Family

8/10

Excellent

04 May 2026

Ann

I reserved a room of a certain type but when I arrived they gave me a horrible dark dank single room on the ground floor with a sliding glass window that had no lock - and to make matters worse, the room's bathroom was outside the room in a nearby hallway. I REFUSED the assignment when I saw it.

To the hotel's credit, they immediately put me up for one night in a MEMBER'S available unit - B404 - an ocean facing suite on the highest hill which was lovely.