Fleet Holiday Rentals from NZ$309: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Fleet holiday rentals

A beach with people, a large striped tower, and buildings in the background.

1. The Sailors Studio|Sleeps2|Weymouth Beach|

Weymouth Town Center

includes taxes & fees

11 Oct - 12 Oct

A cozy living room with a green sofa, a dining table set with plates and cups, and a variety of wall art.

2. Cosy Peacehaven. Free on site Parking! Pet friendly!

Weymouth Town Center

Chloe

includes taxes & fees

11 Oct - 12 Oct

A compact kitchen with a built-in oven, a stainless steel range hood, and a window above the sink.

3. Walkersbase - Nutallergy Friendly - Stay3 - Petsok

Bridport

includes taxes & fees

4 Nov - 5 Nov

A bathroom with a window, a sink, and two potted plants.

4. Hardy View Farm House

Dorchester

Carol S.

includes taxes & fees

26 Oct - 27 Oct

A beach with a natural rock arch formation.

5. Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

Wool

Kristina

includes taxes & fees

19 Oct - 20 Oct

A stone house with a thatched-roof extension, a stone well, and a grassy yard.

6. The Apple House at Moorbath Farm

Bridport

christopher b.

includes taxes & fees

14 Oct - 15 Oct

A living room with a television, dark-colored furniture, a white door, and a window with blinds.

7. Chandlers Nook

Portland

includes taxes & fees

12 Oct - 13 Oct

A brick house with a sloped roof, a patio with a table and chairs, and a garden with various plants.

8. Battys Barn at Moorbath Farm

Bridport

James A.

includes taxes & fees

14 Oct - 15 Oct

A two-story house with a sloped roof, a front porch with chairs, and a small garden area.

9. Cosy country cottage for couples

BRIDPORT

includes taxes & fees

22 Oct - 23 Oct

A row of colorful beach huts with numbered doors, each featuring a small window and a door handle.

10. Holiday Cottage with seafront beach hut - sleeps 4

Lyme Regis

Shane H.

includes taxes & fees

21 Oct - 22 Oct

A cozy room with exposed brick walls, wooden beams, and a mix of leather and fabric seating.

11. The Old Police House, sleeps 10, 1850,s cottage, Family Stay!

Winterborne Whitechurch

"Excellent cottage! Super quirky and perfect for a large group. My husband’s family all met at the Langham vineyard (jut 8 minute’s drive up the road from the accommodation) to celebrate his 50th ; adults, kids, dog…we had a wonderful time and carried on the celebrations with an evening of chat in the comfortable lounge and some food in the spacious dining area before heading to bed (all 10 of us). Martin was a wonderful host, very quick responses and super accommodating. The whole area is...

Stacia B.

includes taxes & fees

2 Nov - 3 Nov

A cozy living room with a grey sofa, a green throw blanket, and a dining area with wicker chairs.

12. 2 Bathsheba Terrace

Dorchester

Rachael

includes taxes & fees

20 Oct - 21 Oct

13. Hide-a-way

Weymouth

includes taxes & fees

20 Oct - 21 Oct

A bedroom with a green upholstered headboard, a floral bedspread, and a painting of flowers on the wall.

14. Rodwell Holt

Weymouth

includes taxes & fees

14 Oct - 15 Oct

A residential property with a patio, a sliding glass door, and a brick exterior.

15. Cedar Drive

Weymouth

David

A spacious kitchen with a dining area, a grey sofa, and a vintage trunk.

16. Mermaid Cottage

Portland

Terry

includes taxes & fees

12 Oct - 13 Oct

A coastal view with boats on the water, a sandy beach, and a clear sky.

17. Beach View House

Wyke Regis

Arve Moen

includes taxes & fees

22 Oct - 23 Oct

A grassy area with a view of a calm body of water and distant landforms.

18. Lobster Cottage

Rodwell

Sharon

includes taxes & fees

17 Oct - 18 Oct

A coastal residential area with houses, a grassy field, and a beach with colorful kayaks.

19. Home From Home

Portland

includes taxes & fees

13 Oct - 14 Oct

A bedroom with a bed, a wooden chair, a desk with a mirror, and a window with curtains.

20. Sea Spray

Overcombe

includes taxes & fees

17 Oct - 18 Oct

View all properties

Find holiday rentals that suit your style

Apartments

Private holiday homes

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Fleet Hotel Reviews

The Jubilee Hotel East- with Spa Facilities

8/10 Good

"The staff were all helpful and friendly. Our room was clean and we had a sea view room. Only thing was because the building is old that the sash window didn't close right. Breakfast was very good."

The Bull Hotel

8/10 Good

"Late online-booking led to some issues with the location end parking nearby. Which was professionally and friendly solved by the staff. The room was rather small for two. Though the bathroom was OK and clean. The hotel has an historical flair and still many original features. Breakfast was plenty een very good. We stayed for one night."

The Jubilee Hotel West- with Spa Facilities

10/10 Excellent

"The room was a good size, we had a family room for 5. The room was clean and tidy and good amenities in the room itself. The best aspect was the seaview which was fantastic helped by some good October weather. We didn't use the bar much as we were visiting relatives who live in Weymouth - but it looked good with plenty to do. The best thing about staying in the older hotels on the front is access to the beach/Weymouth centre, room size and view. Overall very happy with the hotel and the price. Would definitely stay again - thanks."

Belhuish Farmhouse

10/10 Excellent

"This property is unique and rare - owned by an innkeeper who welcomes you to his table with warm hospitality and decades of history to share. Mr. Miller is a wealth of information and retired thatcher. This is not a place for you if you need a well-appointed hotel to feel good about leaving your home. This is a historic property with purbeck flag stones and Welsh slate on the kitchen floor. The stove is as wide as your arms. There are wild pheasants in the fields and silent nights nestled in a hidden valley a bit off the main road. This a place where ruins of the past sit on the land beside a welcoming farmhouse. Great for introverts, writers, couples, families, and solo travelers. Backpackers will love it."

Find out more about Fleet

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Fleet holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Fleet. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Fleet. Seeing all the best attractions is bound to make you fall in love with Fleet. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Fleet short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Fleet?

Yes, there are holiday rentals close to the most popular sights in Fleet, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Fleet has to offer?

Holiday Home of the Year | Sleeps 20 | Tennis, Gardens | 1m Jurassic Coast Beach: This holiday home rental outside of Fleet is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Fleet?

Chesil Beach and Dorset and East Devon Coast are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Dorset National Landscape and Weymouth Harbour.

What are holiday rentals like in Fleet?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Fleet. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for family gatherings.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Fleet holiday rentals

1. The Sailors Studio|Sleeps2|Weymouth Beach|

2. Cosy Peacehaven. Free on site Parking! Pet friendly!

3. Walkersbase - Nutallergy Friendly - Stay3 - Petsok

4. Hardy View Farm House

5. Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

6. The Apple House at Moorbath Farm

7. Chandlers Nook

8. Battys Barn at Moorbath Farm

9. Cosy country cottage for couples

10. Holiday Cottage with seafront beach hut - sleeps 4

11. The Old Police House, sleeps 10, 1850,s cottage, Family Stay!

12. 2 Bathsheba Terrace

13. Hide-a-way

14. Rodwell Holt

15. Cedar Drive

16. Mermaid Cottage

17. Beach View House

18. Lobster Cottage

19. Home From Home

20. Sea Spray

Find holiday rentals that suit your style

Top Fleet Hotel Reviews

The Jubilee Hotel East- with Spa Facilities

Heights Hotel

The Bull Hotel

The Jubilee Hotel West- with Spa Facilities

The Frampton Arms

Best Western Weymouth Hotel Rembrandt

George Albert Hotel & Spa

Belhuish Farmhouse

Sleeping Bear Hotel Dorchester

Find out more about Fleet

Frequently asked questions

Go further with the Expedia app