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Cottages in Bailey's Bay

Our top choices for Bailey's Bay cottages

Sand Dollar 2 Bedrm Beachfront house on private Marley Beach with beach views.

9.8 out of 10, Exceptional, (98)
"Sand Dollar was exactly what we needed for our week in Bermuda - amazing beach & accommodations and great access to the bus line too "
Sand Dollar 2 Bedrm Beachfront house on private Marley Beach with beach views.

Waterfront 2 Bedroom Cottage, Access to Private Beach

9.6 out of 10, Exceptional, (54)
"Spacious and charming two bedroom cottage in a fantastic location."
Waterfront 2 Bedroom Cottage, Access to Private Beach

Pool House Studio In A Garden Setting + EV chargers

10.0 out of 10, Exceptional, (122)
"This property was perfect in every way. We loved the location and it is so well kept and peaceful. Chris and Gail are very helpful and we loved chatting. And last but not least we also ejoyed Tilley the yellow lab. We hope to return!"
Pool House Studio In A Garden Setting + EV chargers

Stunning sunsets, turtle watching, longtails wheeling and glow worms ....

9.8 out of 10, Exceptional, (160)
"3rd stay at this house, loved it again . Thanks Christine !"
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....

Magical private estate:3 bed Sage Cottage,big porch near Cambridge Beaches & fun

9.4 out of 10, Exceptional, (29)
"Stayed with our two teen grandsons and we all had plenty of room to spread out. Towels, dish and bath supplies all provided, along with things like salt, pepper, oil, basic condiments and spices. Location is near the bus line and ecars can be rented from Oleander and picked up at the nearby resort, Cambridge Beaches.Hosts Tom and Hartley are brothers and part of an old island family. They are a wealth of local information!"
Magical private estate:3 bed Sage Cottage,big porch near Cambridge Beaches & fun

Sea Song 3 Bdrm Beachfront house on Marley Beach with great beach and sea views.

9.8 out of 10, Exceptional, (82)
"The house was amazing! Perfect location, easy to walk to other beaches, super convenient for having the bus stop at the bottom of the driveway. Loved it and can't wait to come back!"
Sea Song 3 Bdrm Beachfront house on Marley Beach with great beach and sea views.

Charming , Comfortable Cottage Near Amenities

10.0 out of 10, Exceptional, (93)
"Thomas was very helpful and went out of his way to make the stay more enjoyable ."
Charming , Comfortable Cottage Near Amenities

PalmSprings Accommodations - 3 Bedroom Cottage Near Horseshoe Bay

9.8 out of 10, Exceptional, (12)
"The host met us at the property to make sure we understood how to use the entry code. She was "
PalmSprings Accommodations - 3 Bedroom Cottage Near Horseshoe Bay

Ocean Side Studio Cottage - Condé Nast recommended

10.0 out of 10, Exceptional, (21)
"Fantastic all around - location, cleanliness, and hosts. "
Ocean Side Studio Cottage - Condé Nast recommended

Tranquil Garden Setting, Private Waterfront - Sleeps 6, Twizy charger.

10.0 out of 10, Exceptional, (96)
"Everything about this cottage was lovely; from the decor, the size, the location, the well stocked kitchen and the grounds. We had a wonderful relaxing time. Highly recommend."
Tranquil Garden Setting, Private Waterfront - Sleeps 6, Twizy charger.

NEW LISTING - Stunning sunsets, turtle watching longtails wheeling & glow worms

2.0 star property
8.0 out of 10, Very Good, (2)
"10/10! The house is fantastic but the location is a dream come true! Looking out from the patio table at fish playing in the coral reef below, snorkeling and paddleboarding, seeing the most amazing sunrises and sunsets, and walking just across the street to the ferry or bus to get to the touristy areas... One of the best trips our family will ever get to take. We will be back!"
NEW LISTING - Stunning sunsets, turtle watching longtails wheeling & glow worms

2 Units Combined - Include private dock and Lovely Water Views

9.8 out of 10, Exceptional, (8)
"Very helpful host. Beautiful rental, well appointed kitchen, lovely patio, comfortable beds great place for the family to gather for a out of town wedding."
2 Units Combined - Include private dock and Lovely Water Views

The Boathouse: Large Waterfront Cottage on Harrington Sound – Sleeps 4+

10.0 out of 10, Exceptional, (9)
"Not only is Bermuda beautiful- staying at the Boathouse wonderful! Great beach, dock- the views- awesome. could not have been closer to bus stops… both ways! Comfortable wonderful week at the Boathouse!"
The Boathouse: Large Waterfront Cottage on Harrington Sound – Sleeps 4+

Dreamscape Cottage POOL*VIEWS*MODERN*ELECTRICCARCHARGE

9.8 out of 10, Exceptional, (75)
"This is the perfect hideaway stay. Clean, very nicely decorated and tucked away from noise and crowds. Everything is so accessible. And they have an electric car charging station and a parking spot for your rental. We used Rugged Rental for our vehicle which significantly improved our ability to comfortably get around and see more and do more. This host responds to questions in a very timely manner which lead to my choice of stay. We loved this place and will book again in the future!"
Dreamscape Cottage POOL*VIEWS*MODERN*ELECTRICCARCHARGE

Coral Suite - close to beaches/kayaks/dock/stunning views/EVcharger

9.8 out of 10, Exceptional, (6)
"A small, clean, well-equipped apartment that is a great jumping off point for exploring the wonders of Bermuda."
Coral Suite - close to beaches/kayaks/dock/stunning views/EVcharger

Charming New Waterfront One Bedroom Loft Apartment On Mullet Bay St. George’s

10.0 out of 10, Exceptional, (93)
"2nd time staying here. A beautiful place in St George’s. 5 min from buses to everywhere and St George’s main Square is a 10 min walk. Already planning for next year. Quiet, clean, beautiful place. "
Charming New Waterfront One Bedroom Loft Apartment On Mullet Bay St. George’s

Cozy Gombey Cottage

10.0 out of 10, Exceptional, (5)
"We enjoyed our stay very much. Super clean and very cozy and wonderful hospitality. Thank you for making us feel at home."
Cozy Gombey Cottage

"OceanView" Beach House, Grape Bay Beach, Paget

"OceanView" Beach House, Grape Bay Beach, Paget

Charming Historical 1-bedroom cottage in central Bermuda with WiFi, AC

Charming Historical 1-bedroom cottage in central Bermuda with WiFi, AC

Charming Secluded Garden Setting cottage with WiFi and AC in lovely Sandys

Charming Secluded Garden Setting cottage with WiFi and AC in lovely Sandys
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bailey's Bay Hotel Reviews