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Fleet Vacation Rentals

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Our top choices for Fleet vacation rentals

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

Cosy Peacehaven. Free on site Parking! Pet friendly!
Weymouth Town Center
9.4 out of 10, Exceptional, (3 reviews)
"Perfect flat which contained everything we needed for a great stay. It is in an excellent location and parking was a great bonus to us. Communication was great with clear instructions and thoughtful little extras."
United Kingdom
Chloe
The price is CA $142
CA $207 total
includes taxes & fees
Nov 8 - Nov 9
Cosy Peacehaven. Free on site Parking! Pet friendly!

2. Hardy View Farm House

Hardy View Farm House
Dorchester
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely Fabulous Stay at this Farmhouse. Wonderful hosts in Luba and Chris who were so informative and helpful.Lovely property inside and out. So relaxing and peaceful. Missing the wonderful breakfasts already. 10 out of 10 !!"
Australia
Carol S.
The price is CA $269
CA $288 total
includes taxes & fees
Nov 2 - Nov 3
Hardy View Farm House

3. 2 Bathsheba Terrace

2 Bathsheba Terrace
3.0 star property
Dorchester
10.0 out of 10, Exceptional, (3 reviews)
"Everything was there that we needed. It was clean, well laid out and comfortable. "
Canada
Rachael
The price is CA $617
CA $741 total
includes taxes & fees
Nov 21 - Nov 22
2 Bathsheba Terrace

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

Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World
Wool
10.0 out of 10, Exceptional, (5 reviews)
"The house was outstanding, probably the best we’ve ever experienced. It is exceptionally clean, comfortable for our family of 5, and convenient to the sites in the area. We would stay there again if we return."
United States
Kristina
The price is CA $168
CA $488 total
includes taxes & fees
Nov 2 - Nov 3
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

5. The Apple House at Moorbath Farm

The Apple House at Moorbath Farm
Bridport
10.0 out of 10, Exceptional, (6 reviews)
"Really nice property ,all nicely finished to a high standard.liked the oak used. We had a nice few days-if you want somewhere peaceful and quiet this is ideal. "
United Kingdom
christopher b.
The price is CA $187
CA $327 total
includes taxes & fees
Nov 29 - Nov 30
The Apple House at Moorbath Farm

6. Cosy country cottage for couples

Cosy country cottage for couples
BRIDPORT
9.4 out of 10, Exceptional, (6 reviews)
"We had a great stay ...house was lovely, well equipped & communication was very good with owner."
United Kingdom
Tracey H.
The price is CA $281
CA $420 total
includes taxes & fees
Nov 2 - Nov 3
Cosy country cottage for couples

7. Battys Barn at Moorbath Farm

Battys Barn at Moorbath Farm
Bridport
10.0 out of 10, Exceptional, (7 reviews)
"Host was very helpful with good communication. The property was very well presented and very clean. It was a really nice stay."
United Kingdom
James A.
The price is CA $259
CA $400 total
includes taxes & fees
Nov 2 - Nov 3
Battys Barn at Moorbath Farm

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

The Old Police House, sleeps 10, 1850,s cottage, Family Stay!
Winterborne Whitechurch
10.0 out of 10, Exceptional, (2 reviews)
"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...
United States
Stacia B.
The price is CA $599
CA $621 total
includes taxes & fees
Nov 2 - Nov 3
The Old Police House, sleeps 10, 1850,s cottage, Family Stay!

9. Blue Horizons seaside flat in town centre

Blue Horizons seaside flat in town centre
Lyme Regis
10.0 out of 10, Exceptional, (1 review)
"Very clean, David couldn’t have been more helpful and it was in a lovely area"
United Kingdom
riley n.
The price is CA $247
CA $400 total
includes taxes & fees
Nov 2 - Nov 3
Blue Horizons seaside flat in town centre

10. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

2 bedroom accommodation in Glanvilles Wootton, near Sherborne
Glanvilles Wootton, near Sherborne
10.0 out of 10, Exceptional, (30 reviews)
"The accommodation was very spacious and the hospitality was great"
United Kingdom
Caroline H.
The price is CA $537
CA $537 total
includes taxes & fees
Nov 16 - Nov 17
2 bedroom accommodation in Glanvilles Wootton, near Sherborne

11. Chandlers Nook

Chandlers Nook
3.0 star property
Portland
The price is CA $600
CA $721 total
includes taxes & fees
Nov 5 - Nov 6
Chandlers Nook

12. Rodwell Holt

Rodwell Holt
3.0 star property
Weymouth
The price is CA $692
CA $830 total
includes taxes & fees
Nov 5 - Nov 6
Rodwell Holt

13. Cedar Drive

Cedar Drive
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"So clean I could roll around in the property, also very thoughtful of the host, even a fly squatter was available. Would highly recommend if you’re in the area."
United Kingdom
David
The price is CA $894
CA $1,073 total
includes taxes & fees
Nov 11 - Nov 12
Cedar Drive

14. Hide-a-way

Hide-a-way
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (2 reviews)
"It was in a peaceful location, although a bit far for walking into town. But the facilities were spot on, though there is no oven to cook proper meals. For someone who needs a quiet, chilled out, restful timeout, it is the perfect place to stay."
United Kingdom
Kim
The price is CA $640
CA $768 total
includes taxes & fees
Nov 6 - Nov 7
Hide-a-way

15. Lobster Cottage

Lobster Cottage
3.5 star property
Rodwell
10.0 out of 10, Exceptional, (2 reviews)
"The property was clean and included everything you would need. The outside space was disappointing as it was just a table and chairs in a small concrete space rather than what is shown on the pictures depicting the outside space. The location made ot easy to score with a few shops, pubs and places near by."
United Kingdom
Sharon
The price is CA $781
CA $937 total
includes taxes & fees
Nov 7 - Nov 8
Lobster Cottage

16. Coastguard Lookout

Coastguard Lookout
3.0 star property
Wyke Regis
The price is CA $782
CA $939 total
includes taxes & fees
Nov 7 - Nov 8
Coastguard Lookout

17. Sea Spray

Sea Spray
3.0 star property
Overcombe
The price is CA $826
CA $991 total
includes taxes & fees
Nov 9 - Nov 10
Sea Spray

18. The Little Cottage

The Little Cottage
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"Clean cottage, great location, comfortable beds."
Australia
Lea
The price is CA $896
CA $1,075 total
includes taxes & fees
Nov 5 - Nov 6
The Little Cottage

19. Day Cottage

Day Cottage
3.0 star property
Weymouth Town Center
10.0 out of 10, Exceptional, (1 review)
"The cottage was absolutely excellent , clean, had everything you need,cosy, couldn’t ask for more ,also not far from the beach "
United Kingdom
Cindy
The price is CA $619
CA $743 total
includes taxes & fees
Nov 6 - Nov 7
Day Cottage

20. Old Higher Lighthouse Branscombe Lodge

Old Higher Lighthouse Branscombe Lodge
3.0 star property
Portland
10.0 out of 10, Exceptional, (1 review)
"This property was absolutely amazed and having Access to one of the first lighthouses there "
United Kingdom
Trevor
The price is CA $817
CA $981 total
includes taxes & fees
Nov 5 - Nov 6
Old Higher Lighthouse Branscombe Lodge
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 Fleet Hotel Reviews

Find out more about Fleet

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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Frequently asked questions

Are there vacation rentals in Fleet?

Yes, you can find vacation rentals close to the most popular points of interest in Fleet, or you can select a more remote option if you're looking for a relaxing stay.

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

Holiday Home of the Year | Sleeps 20 | Tennis, Gardens | 1m Jurassic Coast Beach: This vacation home rental outside of Fleet is located in a rural location and has a fireplace, a patio, and a barbecue grill 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 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 larger area, you’ll find Dorset National Landscape and Weymouth Harbour.

What are vacation rentals like in Fleet?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Fleet. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for small groups.