Chesapeake Beach Resort

3.5 star property
Hotel on the beach, with 2 outdoor pools

Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun-loungers, beach towels
Water view
Outdoor spa tub
Balcony
Hypo-allergenic bedding, pillow-top beds, laptop workspace

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Bar
  • 24/7 front desk
The current price is NZ$331
includes taxes & fees
17 Dec - 18 Dec

Explore the area

View map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Place, History of Diving Museum
    ‪12 min walk‬
  • Place, Theater of the Sea
    ‪3 min drive‬
  • Place, Islamorada Brewery & Distillery
    ‪3 min drive‬

Room options

Ocean View Queens

9.8 out of 10
Exceptional
(43 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillow-top bed
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Ocean View King

9.4 out of 10
Exceptional
(86 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

ADA Ocean View King Suite

8.0 out of 10
Very good
(3 reviews)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 50 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed

ADA Ocean View King

8.6 out of 10
Excellent
(17 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillow-top bed
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

ADA Ocean View Queens

9.0 out of 10
Wonderful
(7 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Separate bedroom
  • 34 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Hearing Impaired Ocean View Queens

10.0 out of 10
Exceptional
(2 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillow-top bed
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Hearing Impaired Ocean View King Suite

8.6 out of 10
Excellent
(4 reviews)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 50 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

Standard Queens

9.4 out of 10
Exceptional
(56 reviews)

Highlights

Deck/patio
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillow-top bed
  • 29 sq m
  • Sleeps 4
  • 2 Queen Beds

Standard Doubles

9.2 out of 10
Wonderful
(92 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillow-top bed
  • 25 sq m
  • Sleeps 4
  • 2 Double Beds

Standard King with Sleeper Sofa

9.0 out of 10
Wonderful
(21 reviews)

Highlights

Deck/patio
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 29 sq m
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

Standard King

9.4 out of 10
Exceptional
(31 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillow-top bed
  • 25 sq m
  • Sleeps 3
  • 1 King Bed

Ocean View King Suite

9.4 out of 10
Exceptional
(16 reviews)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 49 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

Deluxe Ocean View Two Queen Suite

8.8 out of 10
Excellent
(9 reviews)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
  • 60 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)

Highlights

Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dishwasher
HDTV
Hypo-allergenic bedding
  • 60 sq m
  • 2 bedrooms
  • Resort view
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed

Standard King Villa

Highlights

Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
HDTV
Hypo-allergenic bedding
Renovated in 2020
Separate bedroom
  • 30 sq m
  • 1 bedroom
  • Resort view
  • Sleeps 3
  • 1 King Bed

King Efficiency Villa

10.0 out of 10
Exceptional
(2 reviews)

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
Dishwasher
  • 48 sq m
  • 1 bedroom
  • Resort view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

ADA King Efficiency Villa

Highlights

Separate dining area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
HDTV
Hypo-allergenic bedding
  • 48 sq m
  • 1 bedroom
  • Resort view
  • Sleeps 3
  • 1 King Bed

Premium 1-Bedroom Ocean View Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
Dishwasher
  • 65 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed

Premium Ocean View King Villa

Highlights

Patio
Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
  • 77 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

Ocean View King Efficiency Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dishwasher
HDTV
  • 48 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

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About the area

Islamorada

At Chesapeake Beach Resort you'll be within a 15-minute walk of History of Diving Museum and 1.8 km (1.1 mi) from Windley Key Fossil Reef Geological State Park. Highlights at this beachfront hotel include 2 outdoor swimming pools, a private beach and a marina. .Tiki Bar is the hotel's own bar. Enjoy the pool loungers along with access to boat tours and kayaking. Added amenities include free Wi-Fi in public areas, coffee/tea in a common area and free use of bicycles. Free continental breakfast is available daily between 6:00 AM and 10:00 AM. .With a stay at this 3.5-property class Matecumbe hotel, you'll be 2 km (1.2 mi) from Islamorada Brewery & Distillery and 2.7 km (1.7 mi) from Keys History & Discovery Center.

What's nearby

  • History of Diving Museum - 12 min walk - 1.1 km
  • Theater of the Sea - 3 min drive - 2.0 km
  • Windley Key Fossil Reef Geological State Park - 3 min drive - 2.0 km
  • Islamorada Brewery & Distillery - 3 min drive - 2.7 km
  • Bud n' Mary's Dive Center - 10 min drive - 7.6 km

Getting around

  • Miami International Airport (MIA) - 91 min drive

Restaurants

  • ‪Tiki Bar - ‬13 min walk
  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Wendy's - ‬2 min drive
  • ‪Starbucks - ‬15 min walk

About this property

Chesapeake Beach Resort

Hotel on the beach, with 2 outdoor pools
Simply walk outside to smell the salty air and watch the ocean waves from the white sand beach. Cool off in one of the 2 outdoor swimming pools at Chesapeake Beach Resort, and enjoy amenities such as a marina and complimentary bicycles.

Free breakfast is available daily. You can enjoy a drink at the bar/lounge. A computer station is on site and WiFi is free in public spaces. A complete renovation of Chesapeake Beach Resort was completed in January 2020.

This 3.5-star Islamorada hotel is smoke free.

  • 60 guestrooms or units
  • 2 levels
  • 9 buildings
  • Built in 2020
  • Continental breakfast (free)
  • Beach lounge chairs
  • Towels for the beach
  • Poolside lounge chairs
  • Coffee in lobby
  • Front desk (24 hours)
  • Staff members are multilingual
  • Concierge
  • Computer for guest use
  • No smoking on site
  • Bar or lounge
Chesapeake Beach Resort offers 60 air-conditioned accommodations, which are accessible via exterior corridors, and features coffee/tea makers and designer toiletries. Beds feature pillowtop mattresses. 43-inch flat-screen televisions come with cable channels. Bathrooms include a shower, complimentary toiletries and hairdryers.

This Islamorada hotel provides complimentary wireless Internet access, with a speed of 100+ Mbps (good for 1–2 people or up to 6 devices). Business-friendly amenities include telephones along with free local calls (restrictions may apply). Additionally, rooms include an iron/ironing board and a ceiling fan. Housekeeping is offered on a daily basis and hypo-allergenic bedding can be requested.

Similar properties

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • In-room WiFi speed: 100+ Mbps (good for 1–2 people or up to 6 devices)
  • Available in some public areas: Free WiFi

Parking and transport

  • Wheelchair-accessible parking available
  • Onsite parking includes off-street options

Food and drink

  • Free continental breakfast available daily 6:00 AM to 10:00 AM
  • A bar/lounge
  • Coffee and tea in common areas

Restaurants on site

  • Tiki Bar

Things to do

  • 2 outdoor pools
  • Boat tours
  • Fishing
  • Free bicycle rentals
  • Kayaking

Family friendly

  • 2 outdoor pools
  • Fenced pool
  • In-room microwave
  • Pool gate

Conveniences

  • 24-hour front desk

Guest services

  • Concierge services
  • Housekeeping (daily)
  • Multilingual staff

Business services

  • Computer station

Outdoors

  • Beach loungers
  • Beach towels
  • Marina
  • On a private beach
  • Pool loungers

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Assistive listening devices
  • Braille/raised signage
  • Handrails in hallways
  • Handrails in stairways
  • Lever door handles
  • Pool hoist on site
  • Upper floors accessible by stairs only
  • Visual alarms in hallways
  • Well-lit path to entrance
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible parking
  • Wheelchair-accessible pool
  • Wheelchair-accessible public bathroom

More

  • 2 floors
  • 9 buildings
  • Built in 2020
  • Renovated entire property - January 2020
  • Smoke-free property
  • Traditional architecture

Room amenities

Bedroom

  • Bedsheets provided
  • Blackout drapes
  • Hypo-allergenic bedding
  • Pillowtop mattress

Bathroom

  • Designer toiletries
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • 43-inch flat-screen TV with cable channels

Food and drink

  • Coffee/tea maker
  • Microwave

More

  • Access via exterior corridors
  • Air conditioning
  • Ceiling fan
  • Free local calls
  • Iron/ironing board
  • Laptop workspace
  • Phone

Policies

Check-in

Check-in start time: 4:00 PM; check-in end time: 3:00 AM
Contactless check-in and check-out are available
Late check-in subject to availability
Minimum check-in age - 18

Check-out

Check-out before 11 AM
Contactless check-out
A late check-out fee will be charged

Special check-in instructions

Front desk staff will greet guests on arrival at the property
Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

  • Pets: USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per stay
  • Maximum 2 (weight limit: 50 lb per pet)
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees.

Children and extra beds

  • Children are welcome.
  • Rollaway/extra beds are not available.

Payment types

Important information

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

  • Pet deposit: USD 50.00 per stay
  • Pet fee: USD 50.00 per accommodation, per night
  • Service animals are exempt from fees
  • A late check-out fee will be charged

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards; cash is not accepted
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Charges for extra guests may apply and vary according to property policy.
A credit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children. If you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room. This property accepts Visa, Mastercard, American Express and Discover. Cash is not accepted. 

We should mention

  • Pool access available from 7:00 AM to 10:30 PM
  • Certain facilities might have restricted access. For details, you can contact the property at the number on the booking confirmation.
  • Guests may experience noise disturbance due to nearby construction work.
  • To make arrangements to bring your pet, contact the property directly at the number on your booking confirmation (please see the Fees section for related charges).

Property is also known as

Chesapeake Beach Islamorada
Chesapeake Beach Resort
Chesapeake Beach Resort Islamorada
Chesapeake Resort
Chesapeake Beach Hotel Islamorada
Chesapeake Beach Resort Hotel
Chesapeake Beach Resort Islamorada
Chesapeake Beach Resort Hotel Islamorada

Frequently asked questions

What is the cancellation policy at Chesapeake Beach Resort?

Chesapeake Beach Resort offers free cancellation on select room rates. Check out the cancellation policy for more info.

How much does it cost to stay at Chesapeake Beach Resort?

As of 16 Dec 2025, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on 17 Dec 2025 start from NZ$331.14, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Are there any beaches close to Chesapeake Beach Resort?

The closest beach to Chesapeake Beach Resort is Anne's Beach (16.1 km).

Does Chesapeake Beach Resort have a pool?

Yep, and guests love it! Chesapeake Beach Resort has 2 outdoor swimming pools. Grab your bathers and lounge poolside while enjoying on a lounger. The pool is open 7:00 AM to 10:30 PM.

What makes Chesapeake Beach Resort a romantic place to stay?

A private beach and a lounge bar, as well as pillowtop beds in the guestrooms, all help set the scene for a romantic weekend at Chesapeake Beach Resort.

Does Chesapeake Beach Resort serve breakfast?

Yep, guests give top marks to the free continental breakfast here! Available daily from 6:00 AM to 10:00 AM, this is the perfect place to fuel up for a big day full of adventure.

Is there a free airport shuttle available at Chesapeake Beach Resort?

No, Chesapeake Beach Resort does not offer an airport shuttle service.

What time are check-in & check-out at Chesapeake Beach Resort?

Check-in begins at 4:00 PM. Check-out time is 11 AM.

Reviews

Chesapeake Beach Resort Reviews

9.2

Wonderful

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

9.0/10

Eco-friendliness
Rating 10 - Excellent. 1161 out of 1595 reviews
Rating 8 - Good. 267 out of 1595 reviews
Rating 6 - Okay. 96 out of 1595 reviews
Rating 4 - Poor. 42 out of 1595 reviews
Rating 2 - Terrible. 29 out of 1595 reviews

Reviews

10/10 Excellent

Logan

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Sep 2025

10/10 Excellent

April

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Relaxation 😌

Such a relaxing and fun spot. Enjoyed snorkeling every day at sunrise and sunset 😍 Can't wait for my next stay 🤗
Stayed 2 nights in Sep 2025

2/10 Terrible

Ori

Disliked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Sep 2025

10/10 Excellent

mariela tumene

Liked: Cleanliness, staff & service, property conditions & facilities
amazing everything
Stayed 1 night in Sep 2025

10/10 Excellent

Gregory

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Great clean beautiful resort, but the road noise!

Centrally located in Islamorada and spotless property. Not a piece of trash anywhere. Comfortable beds, great towels. Resort seems newly built. Beautiful oceanside pool or second more private pool. Lots of loungers and umbrellas all along the beach. Accessible by boat with private lagoon. You can see and probably paddle to the sandbar from there. Only downside to me was highway noise, and neighbor noise. Seems like no soundproofing. You hear the trucks and your neighbors clearly all night long if you are in the cheaper rooms that are non-ocean front/view up closer to the roadway. Bring earplugs. Staff everywhere cleaning and fixing things up. Lots of different room and little “house” options. Property is huge. Kayaks, paddleboards there for a fee.
Stayed 4 nights in Sep 2025

6/10 Okay

David, Village of Lakewood

Travelled with family and small children
Liked: Cleanliness
Disliked: Amenities, property conditions & facilities
I don’t know how this property has a rating of “wonderful”. We checked in during a heavy thunderstorm only to find out that the building our room was located in had no elevator. Upon learning this I told the front desk we are a family of 4 (two young kids) with 4 suitcases and that lugging these up slippery stone stairs in the middle of a storm was a really bad idea. So even though it was not offered, I asked to be moved to a building with an elevator! I was told that would be an extra $200 for the night. I passed and lugged them up with my wife. Then the room was poop. Bathroom door didn’t close all the way - the girls in your family will love that! Shower knob nearly pulled off the wall unless braced with your other hand, no water bottles in the room (paid or otherwise). Pedestal sink with no place to put toiletries, unless on top of the friggen toilet! GM called later that night offering to let us move rooms. Too late- already did the work ourselves and only staying for one night. The right move would have been monetary compensation at this point.
Stayed 1 night in Sep 2025

10/10 Excellent

Joe

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Sep 2025

8/10 Good

Luis

Liked: Cleanliness, staff & service
It was ok
Stayed 1 night in Aug 2025

10/10 Excellent

Arlettis

Liked: Amenities
All good
Stayed 1 night in Sep 2025

8/10 Good

Lester

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Nice...

Very nice staff throughout. The room was nice but has an a/c that runs on the wall all the time. There was also a half in gap on the door to the room that alloeed you to hear all the road noise outside. Breakfast staff and food was great, lagoon kayaking was fun but water not easily accessible except for a thin sand path out into the ocean. Pool was well kept and property very nice.
Stayed 2 nights in Aug 2025

10/10 Excellent

Evelin

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities
All is clean the service is nice 💕
Stayed 1 night in Aug 2025

10/10 Excellent

Felipe

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Sep 2025

8/10 Good

Summer

Liked: Cleanliness, staff & service, property conditions & facilities
Clean, great staff
Stayed 1 night in Sep 2025

10/10 Excellent

Shelby

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very nice resort, clean quiet, two very nice pools!! Great hot tub!! Paddle boards, and kayaks to use staff was very nice!! highly recommend
Stayed 5 nights in Aug 2025

8/10 Good

Gloria

Liked: Cleanliness, staff & service, property conditions & facilities
Excellent view and nice people
Stayed 2 nights in Aug 2025

10/10 Excellent

NICOLA

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property was absolutely amazing! Decorated extremely tasteful, immaculate condition, breakfast was lovely sat outside. Would love to return here.
Stayed 1 night in Aug 2025

8/10 Good

Victoria

Travelled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location, clean rooms, great amenities and the staff is very friendly.
Stayed 3 nights in Aug 2025

10/10 Excellent

Elizabeth

Business traveller
Liked: Property conditions & facilities
I enjoyed my stay. I would stay at this hotel again
Stayed 1 night in Aug 2025

10/10 Excellent

Thomas

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was welcoming and accommodating
Stayed 1 night in Aug 2025

10/10 Excellent

Daniel

Liked: Cleanliness, staff & service, property conditions & facilities
Great place
Stayed 1 night in Aug 2025

10/10 Excellent

Denice

Travelled with family
Stayed 2 nights in Aug 2025

10/10 Excellent

Richard

Travelled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Great location

Awesome resort. Lots of amenities. Great for a weekend getaway. Good restaurants nearby
Stayed 2 nights in Aug 2025

10/10 Excellent

Ernesto

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Perfect Gateway

I would like to thank Venessa for a wonderful seem less check and the champagne welcome and being greated by name was very welcoming the room was very comfortable and the complimentary breakfast was a plus as well as the fact that it is pet friendly with a reasonable fee. I will definitely come back again.
Stayed 2 nights in Aug 2025

10/10 Excellent

Heather

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Villa 1 was Beautiful!

Amazing stay at Villa 1 at the Chesapeake Resort in Islamorado! Beautiful!
Stayed 2 nights in Aug 2025

10/10 Excellent

Dawn, Auburn

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautifully updated property. Staff is very friendly. They are a bit old school in all the paperwork they require however.
Stayed 3 nights in Aug 2025