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Chesapeake Beach Resort

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

Photo gallery for Chesapeake Beach Resort

Relax on the beach with a tranquil ocean view and comfortable sun loungers.
Overlooking the calm waters, this hotel offers stunning views of the surrounding landscape and palm trees.
Enjoy breathtaking ocean views from this balcony overlooking the beach.
Relax by the pool, surrounded by palm trees and a hot tub.
Enjoy a comfortable stay with a large bed, desk, and seating area, plus a window offering a view of the outdoors.

Popular amenities

  • Bar
  • 24/7 front desk
The current price is NZ$348
includes taxes & fees
12 Aug - 13 Aug

Explore the area

Map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Windley Key Fossil Reef Geological State Park
    ‪2 min drive‬
  • Theater of the Sea
    ‪2 min drive‬
  • Florida Keys Brewing Co.
    ‪4 min drive‬

Room options

View all photos for 2-Bedroom Villa

2-Bedroom Villa

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
  • Resort view
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed

View all photos for Standard King

Standard King

Standard King

9.4 out of 10
Exceptional
(28 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

View all photos for King Efficiency Villa

King Efficiency Villa

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
  • Resort view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Doubles

Standard Doubles

Standard Doubles

9.2 out of 10
Wonderful
(85 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

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

9.0 out of 10
Wonderful
(18 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
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Hearing Impaired Ocean View Queens

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

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

View all photos for Hearing Impaired Ocean View King Suite

43-inch flat-screen TV with cable channels, TV

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
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa

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
  • Resort view
  • Sleeps 3
  • 1 King Bed

View all photos for Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa

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
  • Ocean view
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed

View all photos for Deluxe Ocean View Two Queen Suite

Balcony

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
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

View all photos for Ocean View King

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King

9.6 out of 10
Exceptional
(77 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

View all photos for Ocean View King Suite

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King Suite

9.4 out of 10
Exceptional
(13 reviews)

Highlights

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

View all photos for Ocean View Queens

Terrace/patio

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 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
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Queens

Standard Queens

Standard Queens

9.4 out of 10
Exceptional
(53 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

View all photos for Standard King Villa

Standard King Villa

Standard King Villa

Highlights

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

View all photos for Premium Ocean View King Villa

Premium Ocean View King Villa | Living area

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
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for ADA Ocean View Queens

ADA Ocean View Queens

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
Pillow-top bed
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

View all photos for ADA Ocean View King Suite

ADA Ocean View King Suite | Balcony

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
  • Ocean view
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA Ocean View King

8.6 out of 10
Excellent
(16 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

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
  • Windley Key Fossil Reef Geological State Park - 2 min drive - 2.0 km
  • Theater of the Sea - 2 min drive - 2.4 km
  • Florida Keys Brewing Co. - 4 min drive - 4.0 km
  • Bud n' Mary's Dive Center - 7 min drive - 7.3 km

Getting around

  • Miami International Airport (MIA) - 91 min drive

Restaurants

  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Hog Heaven - ‬3 min drive
  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Florida Keys Brewing Co. - ‬3 min drive
  • ‪Whale Harbor Restaurant Marina - ‬2 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.

Languages

English, Spanish

Similar properties

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Amara Cay Resort

  • On private beach
  • Pool
  • Pet-friendly
  • Restaurant
4.4 out of 5, Excellent, 1,236 reviews
The price is NZ$413
includes taxes & fees
1 Sept - 2 Sept
Amara Cay Resort

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

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 2 Aug 2025, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on 1 Sept 2025 start from NZ$347.78, 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.

Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1066 out of 1480 reviews
Rating 8 - Good. 247 out of 1480 reviews
Rating 6 - Okay. 92 out of 1480 reviews
Rating 4 - Poor. 41 out of 1480 reviews
Rating 2 - Terrible. 34 out of 1480 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

8.8/10

Amenities

9.2/10

Property conditions & facilities

9.0/10

Eco-friendliness

Reviews

10/10 Excellent

Anny, Medford

Travelled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We had a Vila and it was very nice, new and very clean. We loved all about it!
Stayed 3 nights in Apr 2025

10/10 Excellent

Peter

Liked: Cleanliness, staff & service, property conditions & facilities
Great property exceeded our expectations.
Stayed 2 nights in Apr 2025

10/10 Excellent

Daniel, Miami

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean, nicely decorated rooms. Direct beach access. Well maintained property.
Stayed 1 night in Apr 2025

10/10 Excellent

Helen

Liked: Cleanliness, staff & service, property conditions & facilities
Amazing location.
Stayed 4 nights in Mar 2025

10/10 Excellent

Wilson

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Todo muy Exelente las habitaciones son muy buenas y limpias recomendadisimo
Stayed 1 night in Apr 2025

6/10 Okay

Patricia

Liked: Cleanliness
was told hot tub was in working order when making the reservation. Hot tub was out of order upon arrival and during stay.
Stayed 1 night in Apr 2025

8/10 Good

Edwin

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Apr 2025

8/10 Good

Adam

Liked: Cleanliness, property conditions & facilities
Good for the price and convenient for fishing trips. No frills, clean rooms good location.
Stayed 3 nights in Apr 2025

10/10 Excellent

Margarita

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Apr 2025

2/10 Terrible

PHILIP

Travelled with family
Disliked: Staff & service, property conditions & facilities
We only stayed 1 night and checked out. We are asking Expedia and Chesapeake to REFUND us for the additional 2 nights!! BKG#73084799299276 APRIL 24-27TH
Stayed 3 nights in Apr 2025

10/10 Excellent

CHASE

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Property was very nice. Staff was very nice also. We thought property had a restaurant and bar but none available yet. They did have free breakfast and great ocean front accommodations
Stayed 3 nights in Apr 2025

10/10 Excellent

monika

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in Apr 2025

10/10 Excellent

Salim, Boca Raton

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location and rooms.
Stayed 2 nights in Apr 2025

10/10 Excellent

Jelena

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nicely remodeled (without the smell of mold) with contemporary touches. We were prepared to find out that pictures will not turn to reality but were so pleased that they reflect what the resort really is. Breakfast is included into stay (thank you to the owner for the omelet station!). Good quality coffee and tea always available at the front desk. Another pleasant surprise was that you could check out bikes/fishing rods or kayaks for a few hours to enjoy. Such a beautiful setting and we cannot wait to return, unless something changes this will be our place to stay at the Keys. Thank you for not cutting corners and making it a pleasant experience for your guests!
Stayed 4 nights in Apr 2025

10/10 Excellent

Jada

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place is amazing the rooms are beautiful and the view is breathtaking.
Stayed 3 nights in Apr 2025

10/10 Excellent

Christopher P

Liked: Staff & service, property conditions & facilities
Stayed 1 night in Apr 2025

10/10 Excellent

david

Stayed 2 nights in Apr 2025

8/10 Good

John

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

10/10 Excellent

Jen

Stayed 1 night in Apr 2025

10/10 Excellent

Dianelis

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excelent
Stayed 1 night in Mar 2025

8/10 Good

Nicole

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful view from room , breakfast included is nice due to price of room
Stayed 4 nights in Apr 2025

8/10 Good

Tom

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

10/10 Excellent

jamie

Stayed 2 nights in Apr 2025

10/10 Excellent

Yoxaris

Stayed 4 nights in Apr 2025

8/10 Good

Kurt, Miami

Travelled with family
We made a stop over at this place on our way from Miami to Ley West. A convienient, nice place with good restaurants near by.
Stayed 1 night in Apr 2025