Chelston Vacation Rentals

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Vacation Rentals in Chelston

Family Thanksgiving 2025 Bermuda! Private Luxury Villa 3 Bedrooms Pool Beach

Paget
10.0 out of 10, Exceptional, (4)
"Fantastic property- conveniently located and as advertised! "
Canada
Adam M.
Family Thanksgiving 2025 Bermuda! Private Luxury Villa 3 Bedrooms Pool Beach

Rosemont Guest Suites

3.5 star property
Pembroke Parish
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 21 - Nov 22
Total with taxes and fees
Rosemont Guest Suites

Seven Arches

3.0 star property
Warwick Parish
9.4 out of 10, Exceptional, (53)
"Excellent stay Will return "
United States
Sherri
Seven Arches

Windsong Guest Apartments

3.0 star property
Pembroke Parish
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

Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!

Devonshire
9.8 out of 10, Exceptional, (127)
"Loved this rental! The owner is so nice, the location is beautiful, and the house is so spacious. Very chill environment, probably not great for anyone who want to be in the center of the action. My group had an amazing time, the ocean access got a little hairy because of the impending hurricane, but when the water was calm, it was perfection. Would definitely stay here again!"
United States
Constance f.
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!

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

Somerset Village
9.8 out of 10, Exceptional, (167)
"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 ....

Pool House Studio In A Garden Setting + EV chargers

Smiths
10.0 out of 10, Exceptional, (125)
"The hosts, Chris and Gail are wonderful. Tilly, their dog, is adorable. The pool house was perfect for us. We went to Bermuda for a wedding, and stayed for a week. We had plenty of room. You can’t beat the location. We highly recommend this property to anyone!"
United States
Dawn
Pool House Studio In A Garden Setting + EV chargers

Tiny Studio in fabulous Smith's Parish at John Smith's Bay Beach

Paget Parish
10.0 out of 10, Exceptional, (2)
"Location "
United Kingdom
clare a.
Tiny Studio in fabulous Smith's Parish at John Smith's Bay Beach

Wild Bird, Paget - Pool, Twizy charger, Kitchenette - non smoking property

Paget
9.8 out of 10, Exceptional, (64)
"It was a great place all the way around. "
United States
keith f.
Wild Bird, Paget - Pool, Twizy charger, Kitchenette - non smoking property

Beach House Chateau West SLEEPS 5- 2 Bed 1Bath Bermy Style

Smith's Parish
9.2 out of 10, Wonderful, (40)
"Property location is a 10! This house is directly across from John Smith's Bay, one of the best beaches in Bermuda. Beach chairs and umbrellas are provided in addition to all necessary kitchen/bath amenities. Bus stops are conveniently located close by. Well stocked grocery store is a quick bus ride away. Property could use some updating, but did not deter our wonderful vacation."
United States
Betty R.
Beach House Chateau West SLEEPS 5- 2 Bed 1Bath Bermy Style

Pre-Thanksgiving, HALF PRICE SALE of 100 Daily, from November 9th. Just request!

5 Cross Bay Road
10.0 out of 10, Exceptional, (150)
"Wendell was an absolutely awesome host! Very friendly and willing to help whenever possible! You can’t beat a better location, just a short walk to the beach and the view is absolutely spectacular! We truly enjoyed our stay in Bermuda! Thank you, Wendell! "
United States
Jim M.
Pre-Thanksgiving, HALF PRICE SALE of 100 Daily, from November 9th. Just request!

Exquisite 1-bedroom Apartment is centrally located in Devonshire Parish.........

Devonshire DV08
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.........

Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!

Sandy's
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!

Tranquil, Roomy Getaway - Close to City of Hamilton

Pembroke
10.0 out of 10, Exceptional, (1)
"Clean, comfortable and exactly as advertised. Close to all amenities and a great location for all of the activities we had planned - good Bermuda value!"
Canada
Thomas W.
Tranquil, Roomy Getaway - Close to City of Hamilton

Stunning Views of Horseshoe Bay Beach. Enjoy the sounds of the lapping waves!

Southampton
10.0 out of 10, Exceptional, (74)
"We were all amazed at the beach view from the house. It was so perfect and we would all stay again there. Jessica was a great hostess who answered every and all our questions and requests. I give this hour a 10 out of 10Stay here, you won’t regret it. "
United States
jackie k.
Stunning Views of Horseshoe Bay Beach. Enjoy the sounds of the lapping waves!

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

Warwick
9.8 out of 10, Exceptional, (101)
"Perfect location, clean and Nice accommodation "
France
Olivier M.
Sand Dollar 2 Bedrm Beachfront house on private Marley Beach with beach views.

Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!

Somerset village
10.0 out of 10, Exceptional, (41)
"Nice, spread out house that provides indoor and outdoor space to congregate but also privacy in bedrooms and bathrooms. 2 minute walk to beach with chairs and umbrellas and 5 minute walk to Somerset long bay beach. Walkable to good size grocery store, a few takeout restaurants and bus stop. The nooks and crannies of the property are amazing. Hammock, moon gate, benches, outdoor showers, so many birds and gorgeous lush foliage surround the house. "
United States
Heather D.
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!

Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment

Sandys
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

Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course

Southampton
10.0 out of 10, Exceptional, (123)
"Amazing property and amazing host "
United States
Robert C.
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course

[A]MOUR AMOUR HEART OF HOSPITALITY!

Hamilton
10.0 out of 10, Exceptional, (41)
"Nice views and location. "
United States
Adriaan
[A]MOUR AMOUR HEART OF HOSPITALITY!
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

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.

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?

Family Thanksgiving 2025 Bermuda! Private Luxury Villa 3 Bedrooms Pool Beach: Visitors give good reviews to this Chelston vacation home rental, which is located next to a golf course and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

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. Hamilton Ferry Dock and Front Street 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.