Chelston Vacation Rentals

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Sep 25 - Sep 26
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Sep 26 - Sep 27
This weekend
Sep 26 - Sep 28
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Oct 3 - Oct 5

Vacation Rentals in Chelston

Rosemont Guest Suites
Outdoor pool

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. "
The price is ￥47,474
￥56,178 total
includes taxes & fees
Sep 27 - Sep 28
Rosemont Guest Suites
Seven Arches
Apartment | Dining room

Seven Arches

3.0 star property
9.4 out of 10, Exceptional, (50)
"Nice property "
Seven Arches
Your Private Luxury Villa - 3 Bedrooms, House & Cottage, Pool, Walk to Beach!
Beach nearby, beach towels

Your Private Luxury Villa - 3 Bedrooms, House & Cottage, Pool, Walk to Beach!

10.0 out of 10, Exceptional, (1)
"Fantastic property- conveniently located and as advertised! "
Your Private Luxury Villa - 3 Bedrooms, House & Cottage, Pool, Walk to Beach!
Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!
Interior

Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!

10.0 out of 10, Exceptional, (115)
"Amazing place Jody has set up! My fiance and I had a wonderful time!"
Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....
Exterior

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

9.8 out of 10, Exceptional, (163)
"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"
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....
Windsong Guest Apartments
Property entrance

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!!!!"
Windsong Guest Apartments
Spacious Beachfront and Private Resort living
On the beach, sun loungers, beach towels

Spacious Beachfront and Private Resort living

9.8 out of 10, Exceptional, (135)
"Fantastic stay. Accurate description. Right on bus route and basically a beautiful private beach. Wonderful hosts. We will come again. "
Spacious Beachfront and Private Resort living
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge 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, (41)
"Overall a very nice property. We like to be off the beaten track and it certainly was."
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course
Pool

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

10.0 out of 10, Exceptional, (122)
"We really enjoyed our stay. Beautiful location and great home for large family gathering. Jessica was immediately responsive in answering questions and helping us when needed. Kids loved the pool, and the nearby beach."
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!
Interior

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

9.8 out of 10, Exceptional, (126)
"the views are breath taking house needs some work but being on the water will beat any property up"
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!
Location! Location! HALF PRICE SALE @ 100 Daily, Sep 25 - Oct 10 & Oct 27- Nov 1
Beach nearby

Location! Location! HALF PRICE SALE @ 100 Daily, Sep 25 - Oct 10 & Oct 27- Nov 1

10.0 out of 10, Exceptional, (146)
"⭐️💌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"
Location! Location! HALF PRICE SALE @ 100 Daily, Sep 25 - Oct 10 & Oct 27- Nov 1
Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment
Property grounds

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

10.0 out of 10, Exceptional, (91)
"This place is fabulous, just like in the pictures. You get your private balcony to watch the sunsets, and walk right down to the ocean for swimming and snorkeling. The owners are super nice and very helpful. The is room comfy and the bed is nice and firm. We would definitely stay here again. Small word of awareness, it is down a steep road, and can be tricky to navigate. Also it requires some up and down hilly walking to the ocean and room, just keep that in mind. Other than that, it's paradise,...
Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!
Property grounds

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

9.8 out of 10, Exceptional, (96)
"We loved our time at this property! The unit was beautifully setup, amazing view all day long, convenient access to bus, walkable to beach and Breezes restaurant. And to top it off the host is great too and even coordinated our transportation to and from airport. Highly recommend! "
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!
Exquisite 1-bedroom Apartment is centrally located in Devonshire Parish.........
Interior

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

10.0 out of 10, Exceptional, (13)
"We had the best stay with Austin. His home is lovely and fully equipped with everything you need. Never had a host take such great care of us. He went above and beyond. Would definitely stay with him again Thanks Austin we had a great time. The Luersens."
Exquisite 1-bedroom Apartment is centrally located in Devonshire Parish.........
Paradise at Limehouse
Fridge, microwave, oven, stovetop

Paradise at Limehouse

9.4 out of 10, Exceptional, (40)
"Excellent stay. Goodwin was very helpful too."
Paradise at Limehouse
The Boathouse: Large Waterfront Cottage on Harrington Sound – Sleeps 4+
Outdoor dining

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

10.0 out of 10, Exceptional, (11)
"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+
Sand Dollar 2 Bedrm Beachfront house on private Marley Beach with beach views.
Beach nearby, sun loungers, beach towels

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

9.8 out of 10, Exceptional, (99)
"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.
Brand New, modern, light, delightful small apartment packed with luxuries
Sun loungers, beach towels

Brand New, modern, light, delightful small apartment packed with luxuries

9.2 out of 10, Wonderful, (25)
"Love it! It was great staying here. Patrick was amazing & attentive. Definitely coming back!"
Brand New, modern, light, delightful small apartment packed with luxuries
Beach House Chateau West SLEEPS 5- 2 Bed 1Bath Bermy Style
Property grounds

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

9.2 out of 10, Wonderful, (38)
"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."
Beach House Chateau West SLEEPS 5- 2 Bed 1Bath Bermy Style
Wild Bird, Paget - Pool, Twizy charger, Kitchenette - non smoking property
Beach nearby, sun loungers, beach towels

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

9.8 out of 10, Exceptional, (63)
"Comfortable and easy to access. Friendly and courteous owner. Great spot for us. "
Wild Bird, Paget - Pool, Twizy charger, Kitchenette - non smoking property
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

Coco Reef Bermuda

Coco Reef Bermuda

10/10 Excellent
"2nd time I have been there, the staff is wonderful and the beach is fantastic"
Gail 3-night trip
Posted 2 days ago
Coco Reef Bermuda

Find out more about Chelston

Find out more about Chelston

Search for holiday rentals in Chelston on Expedia! You can easily find your home rentals, villas, holiday apartments in Chelston using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chelston!

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?

Your Private Luxury Villa - 3 Bedrooms, House & Cottage, Pool, Walk to Beach! : This vacation home rental outside of Chelston 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. 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.