Chelston Vacation Rentals

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Vacation Rentals in Chelston

Outdoor pool
Rosemont Guest Suites
Rosemont Guest Suites
3.5 star property
8.6 out of 10, Excellent, (181)
"Great little quaint local property, clean, a quiet and walkable to Front street shops and restaurants. "
United States
Jennifer
$340 nightly
The price is $377
Nov 8 - Nov 9
Total with taxes and fees
Rosemont Guest Suites
Apartment | Dining room
Seven Arches
Seven Arches
3.0 star property
9.4 out of 10, Exceptional, (52)
"Excellent stay Will return "
United States
Sherri
Seven Arches
Exterior
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....
9.8 out of 10, Exceptional, (166)
"Once again, we really enjoyed our stay. This has to be the best little cottage in Bermuda. Thank you and see you soon. Jo and Ed"
United States
JOANN L.
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....
Interior
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!
9.8 out of 10, Exceptional, (127)
"the views are breath taking house needs some work but being on the water will beat any property up"
United States
bill f.
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!
On the beach, sun loungers, beach towels
Spacious Beachfront and Private Resort living
Spacious Beachfront and Private Resort living
9.8 out of 10, Exceptional, (135)
"This is a lovely property that has all basic features and amenities for a casual comfortable stay. The location is out of this world-overlooking the ocean with just steps down to a secluded beach that feels almost like a private beach. The hosts are very welcoming and accommodating. We look forward to booking with them again. It was an absolutely incredible summer vacation. "
United States
Elena T.
Spacious Beachfront and Private Resort living
Interior
Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!
Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!
10.0 out of 10, Exceptional, (117)
"The apartment was very good, clean and handy to bus stops"
Canada
Helen Yee Wun
Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!
Interior
Exquisite 1-bedroom Apartment is centrally located in Devonshire Parish.........
Exquisite 1-bedroom Apartment is centrally located in Devonshire Parish.........
10.0 out of 10, Exceptional, (14)
"I travel to Bermuda on business several times a year and have stayed at a host of different places from resorts/hotels to rentals and this one is hands down the best so far.Spacious and clean with all of the necessary amenities to make my stay comfortable and enjoyable.The water pressure was the best I've experience on island and having a grocery store less than a 1/2 mile away was super convenient (although it is closed on Sundays).Austin was a great host and I plan on staying with him again!"
United States
Bill M.
Exquisite 1-bedroom Apartment is centrally located in Devonshire Parish.........
Property entrance
Windsong Guest Apartments
Windsong Guest Apartments
3.0 star property
8.8 out of 10, Excellent, (93)
"Place was really clean and big, Roslyn was very caring and helpful. Great place to stay!!!!"
United States
Henry
Windsong Guest Apartments
Beach nearby, beach towels
Family Thanksgiving 2025 Bermuda! Private Luxury Villa 3 Bedrooms Pool Beach
Family Thanksgiving 2025 Bermuda! Private Luxury Villa 3 Bedrooms Pool Beach
10.0 out of 10, Exceptional, (3)
"Fantastic property- conveniently located and as advertised! "
Canada
Adam M.
$720 nightly
The price is $720
Nov 12 - Nov 13
Total with taxes and fees
Family Thanksgiving 2025 Bermuda! Private Luxury Villa 3 Bedrooms Pool Beach
Outdoor dining
Magical private estate:3 bed Sage Cottage,big porch near Cambridge Beaches & fun
Magical private estate:3 bed Sage Cottage,big porch near Cambridge Beaches & fun
9.4 out of 10, Exceptional, (30)
"Loved the uniqueness of the cottage. Comfortable and cozy. "
United States
Dorothy L.
Magical private estate:3 bed Sage Cottage,big porch near Cambridge Beaches & fun
Beach nearby
Location! Location! HALF PRICE SALE @ 100 Daily, November 9th - December 9th ASK
Location! Location! HALF PRICE SALE @ 100 Daily, November 9th - December 9th ASK
10.0 out of 10, Exceptional, (148)
"⭐️💌TOP HOST & LOCATION⭐️💌Perfect 4 Couples Looking for Serenity & a Secure Sanctuary💌⭐️40+YEAR HOST Hospitality & Guidance if Needed💌⭐️PRIVATE ACCESS TO THE BEST SOUTH SHORE~CROSS BAY BEACH⭐️💌Full Amenities on Property w/Transportation Available⭐️💌KINDNESS MATTERS as this is what Host Wendell & his family are all about💓Lynn&Mark, June 2025"
United States
Lynn
Location! Location! HALF PRICE SALE @ 100 Daily, November 9th - December 9th ASK
Exterior
Coral Suite - close to beaches/kayaks/dock/stunning views/EVcharger
Coral Suite - close to beaches/kayaks/dock/stunning views/EVcharger
9.2 out of 10, Wonderful, (7)
"A small, clean, well-equipped apartment that is a great jumping off point for exploring the wonders of Bermuda."
United States
Claire A.
Coral Suite - close to beaches/kayaks/dock/stunning views/EVcharger
On the beach, sun loungers, beach towels
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!
10.0 out of 10, Exceptional, (41)
"Overall a very nice property. We like to be off the beaten track and it certainly was."
United States
Underpressure S.
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!
Property grounds
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!
9.8 out of 10, Exceptional, (98)
"A well provisioned and conveniently located accommodation, with a charming and hospitable host."
Canada
Alix W.
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!
Property grounds
Waterfront 2 Bedroom Cottage, Access to Private Beach
Waterfront 2 Bedroom Cottage, Access to Private Beach
9.6 out of 10, Exceptional, (56)
"We had a wonderful time, super clean and absolutely lovely accommodation. There’s a nice swimming area out the back. Perfectly located right beside the ferry terminal!"
Canada
Kaan C.
Waterfront 2 Bedroom Cottage, Access to Private Beach
Property grounds
Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment
Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment
10.0 out of 10, Exceptional, (93)
"Great sunset from the lawn, great snorkeling, and a comfortable bed. "
United States
James W.
Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment
Pool
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course
10.0 out of 10, Exceptional, (122)
"Loved the property, the incredible views and the responsiveness of host. Great location on the island. "
United States
Martha L.
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course
Exterior
Ocean Side Studio Cottage - Condé Nast recommended
Ocean Side Studio Cottage - Condé Nast recommended
10.0 out of 10, Exceptional, (22)
"We enjoyed our stay so very much. Kilian and Elaine are wonderful hosts and if we return to Bermuda, we'll stay here again. So centrally located, beautiful scenery from the cottage...almost fake! I would highly recommend this cottage, even our taxi driver was so impressed! Thank you Kilian and Elaine for making our first visit to Bermuda so memorable."
United States
Betheny A.
Ocean Side Studio Cottage - Condé Nast recommended
Outdoor pool
“Oceanfront Paradise Property: access to pool, ocean and Complimentary Kayaks”
“Oceanfront Paradise Property: access to pool, ocean and Complimentary Kayaks”
10.0 out of 10, Exceptional, (25)
"This property is in a beautiful location and was exceptionally clean upon arrival. The pool was a highlight, providing endless hours of fun and relaxation for my family. We had a fantastic stay and would definitely return!"
United States
Krysta S.
“Oceanfront Paradise Property: access to pool, ocean and Complimentary Kayaks”
Sun loungers, beach towels
Brand New, modern, light, delightful small apartment packed with luxuries
Brand New, modern, light, delightful small apartment packed with luxuries
9.2 out of 10, Wonderful, (25)
"Great neighborhood, nice and quiet, perfect location "
United States
Robert D.
Brand New, modern, light, delightful small apartment packed with luxuries
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 Chelston Hotel Reviews

The Reefs Resort & Club

The Reefs Resort & Club

10/10 Excellent
"The reefs is a gorgeous and professionally run property that we would highly recommend. We would have rated the staff and service a 5 except for the bar which is staffed by bartenders that are not at all friendly or accommodating. The exception was Jennifer who was a delight! The staff in all other areas is fantastic!!!!! "
TOM 4-night trip
Posted 2 days ago
The Reefs Resort & Club

Find out more about Chelston

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 $377 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.

Explore a world of travel with Expedia

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?

Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!: This vacation home rental outside of Chelston is located by the ocean and has a patio, a selection of games, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.