Chelston Vacation Rentals

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Vacation Rentals in Chelston

Outdoor pool
Rosemont Guest Suites
3.5 star property
8.6 out of 10, Excellent, (131)
"This was the 2nd time that we stayed at the Rosemont, and we were NOT disappointed !! Excellent location to downtown Hamilton (easy walk). Excellent service. Very friendly staff. We will be returning."
Rosemont Guest Suites
Aerial view
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....
9.8 out of 10, Exceptional, (129)
"Book it right now. The yard is unreal, 270 degree water views, your own beach basically, take the kayak out the little islands during low tide.. you can pull up on a deserted beach and walk in the ocean. Great host. Did fire pit every night. Can walk to woodys (so much fun) and the restaurants at Cambridge resort, we also walked to the market, to a local gym, wine store, didn’t even use the bus. I couldn’t complain about any minor thing if there were any, with a view like that.. spectacular"
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....
On the beach
Spacious Beachfront and Private Resort living
9.8 out of 10, Exceptional, (102)
"Lorna and her family are beautiful people. The Gemstones Property is high on a hill overlooking the most beautiful beach (Cross Bay) During our stay we basically had the beach to ourselves. The walk to beach from Gemstones is fairly steep but there are two other routes. It’s not an issue to sway a decision to stay here. We stayed 10 days and our taxi driver Belinda who is a beautiful person stopped in route to gemstone from airport at supermarket so we could buy food, beer and wine etc. We...
Spacious Beachfront and Private Resort living
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Property entrance
Windsong Guest Apartments
3.0 star property
8.8 out of 10, Excellent, (77)
"Great Location. Friendly host and staff"
Windsong Guest Apartments
Apartment | Dining room
Seven Arches
3.0 star property
9.6 out of 10, Exceptional, (25)
"Great accommodations "
Seven Arches
Beach nearby
3 bedroom home with pool
10.0 out of 10, Exceptional, (2)
"Great place to stay! Beautiful house, great beds and comfortable furniture to relax on. The pool off the back door is perfect when you want to skip the beach. The bus stops are a quick walk and after a day or two we were able to figure transportation out. Market across the street came in handy! Leila really went all out for us! She made sure we were comfortable and got in ok. After we asked about transportation from the airport she booked taxi both way! Leila is a great host! We will be back to...
3 bedroom home with pool
Interior
Welcome To Paradise 'AAA' - Private Romantic Getaway!
10.0 out of 10, Exceptional, (91)
"Fantastic location in the village, beautiful view of Mangrove Bay. Very clean with amenities close by. As well, the bus is across the street to take you to Hamilton or Dockyard. Jody is a wonderful host and very attentive. We’ve stayed here 2 years in a row and look forward to returning again. Highly recommend."
Welcome To Paradise 'AAA' - Private Romantic Getaway!
Beach nearby, sun loungers, beach towels
Sunset Paradise Oceanview 1Bedroom Lower Holiday Home Near Beaches
9.6 out of 10, Exceptional, (8)
"We had a fantastic stay. They had all the amenities that we could stay in or all the maps and attraction pamphlets needed to keep busy everyday. Public transportation was near the stores so it was easy to pick up what you need and walk about a block and a half to get back home. We found a restaurant right across the street that made the best fish sandwiches. As someone mentioned the shower is a little small but you can work with it. Over all I recommend this is the place to stay I look forward...
Sunset Paradise Oceanview 1Bedroom Lower Holiday Home Near Beaches
Property grounds
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!
9.8 out of 10, Exceptional, (70)
"Was wanting to stay in the Somerset area for 3 weeks so this was a perfect location for our needs. Well set up for a longer term stay with great kitchen facilities, balcony, close to buses etc. would highly recommend for anyone - especially a longer term stay."
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!
Sun loungers, beach towels
Las Brisas apartment with pool and walk to beach + EV chargers
10.0 out of 10, Exceptional, (64)
"The studio is fully equipped and is well stocked including kitchen basics, toiletries and towels. Gail and Chris are easy going hosts, point you in the right direction and don’t hover. Notes from former guests are welcome. The only issue for us was transportation as we were relying on the bus system which runs from stops just down the hill but doesn’t run at night. Taxis or an electric car rental, both expensive, necessary at times. John Smith Bay Beach with a very good casual bar/grill is...
Las Brisas apartment with pool and walk to beach + EV chargers
Pool
Clairfont, Jobson's Cove / Warwick Long Bay/ Horseshoe Beach - APARTMENT 5
9.8 out of 10, Exceptional, (10)
"Completely satisfied, clean & comfy apt & excellent staff, perfect location! Can't wait to come back!"
Clairfont, Jobson's Cove / Warwick Long Bay/ Horseshoe Beach - APARTMENT 5
Sun loungers, beach towels
Pool House Studio In A Garden Setting + EV chargers
10.0 out of 10, Exceptional, (99)
"Upon arrival we were met by the host, Chris who welcomed us back to the island and answered questions. Pool house is extremely cute and has all necessary things. There is a Lab on the property, Tilly. She is smart and well behaved. Great location! Lovely property and sweet hosts!"
Pool House Studio In A Garden Setting + EV chargers
Beach nearby, sun loungers, beach towels
Two Bedroom with Private Dock near Golf and Beach
10.0 out of 10, Exceptional, (17)
"Rosalyn and Marshall's home is in an excellent location in Southampton. It is close to beaches, the Dockyard, Watson's farm, and golf, all of which we could access either by bus or by taxi driven by a person referred by Rosalyn. We will definitely recommend this property to friends and relatives who are considering a trip to Bermuda."
Two Bedroom with Private Dock near Golf and Beach
On the beach, sun loungers, beach towels
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!
10.0 out of 10, Exceptional, (24)
"We had a ball"
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!
Pool
Luxury Villa with Stunning Views of Horseshoe Bay on the Fairmont Hotel Grounds
10.0 out of 10, Exceptional, (95)
"Mike and Kim were amazing and gracious hosts. We stayed for a long weekend, Thursday-Sunday, and we had everything we needed. The house was beautiful, clean, accommodating, and in an amazing location with a breathtaking view of the beach. Upon our arrival, Mike met us to give a brief tour before running to his pickleball game. Before leaving, he made sure we had everything we needed - Wi-Fi, taxi numbers, etc. He even had some good jokes. Highly recommend"
Luxury Villa with Stunning Views of Horseshoe Bay on the Fairmont Hotel Grounds
Terrace/patio
Magical private estate:3 bed Sage Cottage,big porch near Cambridge Beaches & fun
9.2 out of 10, Wonderful, (15)
"We loved our stay at Sage Cottage. The house is magical. Fresh flowers awaited us in the kitchen and living room on our arrival - we found everything we needed for the rest of our stay. Thank you Tom and Victoria! Beth"
Magical private estate:3 bed Sage Cottage,big porch near Cambridge Beaches & fun
Interior
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!
9.8 out of 10, Exceptional, (116)
"John was a wonderful host and very helpful. The house is in a beautiful location right on the water. The bus stop across the street was very convenient. The only complaint is that the house needs some TLC. Some light bulbs were out. There was some rust on appliances, in the bathrooms and on the outdoor furniture."
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!
Beach | Beach nearby
MEMORIAL DAY WEEKEND SALE at Whispering Waves HALF PRICE of 100 Daily, BOOK NOW
9.8 out of 10, Exceptional, (119)
"Wendell greeted us warmly. We arrived a bit early from airport. The grounds were tidy. The actual room was older, needing some updates. There were some leftover personal care item’s left in a bathroom drawer with a chunk of old dried up bread. But bathroom was clean otherwise. Floors were clean which is important. The a/c worked well. We typically spend very little time in our room, we are not real particular. We would possibly stay again for future visits."
MEMORIAL DAY WEEKEND SALE at Whispering Waves HALF PRICE of 100 Daily, BOOK NOW
Pool
Brand New, modern, light, delightful small apartment packed with luxuries
9.0 out of 10, Wonderful, (19)
"The property was very clean, and very accurate to what we were expecting. The owner was very prompt in replying to our many questions, and was very helpful. The island itself is stunning, and we will definitely return!"
Brand New, modern, light, delightful small apartment packed with luxuries
Interior
Ocean Front, 2 bedroom in Historic St. George
10.0 out of 10, Exceptional, (7)
"This was a beautiful place to stay and the view was amazing. Everyone on the Island was so friendly and helpful with things to do and see. We had a wonderful time in Bermuda."
Ocean Front, 2 bedroom in Historic St. George
Don't see what you're looking for?
See all available properties in Chelston
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.

Chelston Vacation Rental Travel Info

Number of vacation rentals
3
Popular accommodation
Chelston private vacation homes
Known landmarks
Masterworks Museum of Bermuda Art, Bermuda Botanical Gardens and Camden House
International airport
St. George's (BDA-L.F. Wade Intl.)

Other types of properties in Chelston you may be interested in

Couples treatment rooms, body treatments, aromatherapy
Grotto Bay Beach Resort
4.0 star property
8.8 out of 10, Excellent, (1008)
"Hotel staff was fantastic. Located close to airport—huge plus fly out in the am and be on beach for lunch. Food was delicious -catch of day was great! Some of the hotel was being refurbished . "
The price is $510
$596 total
includes taxes & fees
Jun 23 - Jun 24
Grotto Bay Beach Resort
Private beach nearby, white sand, free beach shuttle, beach cabanas
Hamilton Princess & Beach Club - a Fairmont Managed Hotel
4.5 star property
9.2 out of 10, Wonderful, (1002)
"Large property with all of the amenities you need. The rooms in the main building are well appointed and the staff is extremely attentive. Front Street is a 10 min walk or 3 min taxi away. "
The price is $662
$799 total
includes taxes & fees
Jun 16 - Jun 17
Hamilton Princess & Beach Club - a Fairmont Managed Hotel
Exterior
The St. Regis Bermuda Resort
5.0 star property
8.6 out of 10, Excellent, (86)
"View was spectacular, staff great. Food and dining limited, many shortages, boring menu, one restaurant. Too far from everything, expensive to get to points. Too far north."
The price is $849
$1,053 total
includes taxes & fees
Jun 3 - Jun 4
The St. Regis Bermuda Resort
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.

Everything you need to know about Chelston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chelston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chelston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chelston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chelston. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chelston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chelston rentals

At Expedia, we put the best Chelston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chelston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chelston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chelston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Chelston?

Yes, we have vacation rentals near popular attractions in Chelston, or you can go with a more remote option if you're looking for relaxation.

What's the top vacation rental that Chelston has to offer?

Rose Villa House: This vacation home rental outside of Chelston has laundry facilities and WiFi to help you feel perfectly comfortable in your new surroundings.

What’s there to see and do in Chelston?

Explore the area and family-friendly sights such as Bermuda Aquarium Museum and Zoo (BAMZ), or get out into nature at a spot like Elbow Beach. Front Street and Hamilton Ferry Dock are a couple of places you'll find in the larger area.

What’s a vacation rental in Chelston like?

A vacation rental is a private property you can book for a few weeks or just a few days in Chelston. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family trip.

Recent reviews of Chelston properties
Expedia verified reviews

Coco Reef Bermuda

Coco Reef Bermuda

5/5 Excellent
"Coco Reef is a beautiful hotel with a gorgeous beach. They have renovated most of their rooms. The front desk staff was not the best. Very friendly but did not follow through after saying they would take care of something. The cleaning staff was fabulous and very helpful. Grocery store down the street was convenient. We will definitely be back :)"
A verified traveler from telford stayed at Coco Reef Bermuda
Posted 2 days ago
Coco Reef Bermuda