A calm lake with several boats, a sandy shore, and a forested hill in the background.

Whippingham Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Whippingham vacation rentals

A row of terraced houses by a waterfront, with a clear view of the sea.

1. Bell Cottage

Bell Cottage
Cowes
10.0 out of 10, Exceptional, (8 reviews)
"Anonymous: Accommodation lovely. Owners seem to have thought of everything to make our stay very pleasant. Nicely situated to explore the Island. Enjoyed our stay."
United States
Anonymous traveller
The price is CA $1,084
CA $1,277 total
includes taxes & fees
Sep 4 - Sep 5
Bell Cottage
A modern living room with a sofa, coffee table, and a painting of boats.

2. York Street

York Street
Cowes
10.0 out of 10, Exceptional, (8 reviews)
"It was absolutely perfect ! The house was so well looked after ."
United States
Anonymous traveller
The price is CA $1,626
CA $1,893 total
includes taxes & fees
Sep 8 - Sep 9
York Street
A modern living room with a sofa, a TV, and a dining area with a table set for two.

3. 2 bedroom accommodation in East Cowes

2 bedroom accommodation in East Cowes
East Cowes
9.4 out of 10, Exceptional, (6 reviews)
"Brilliant place to stay, welcoming, clean, warm, and well equipped. Easy to visit other places on the IOW and close to terminal on arrival and departure.Would highly recommend"
United States
Mary Pape
The price is CA $1,046
CA $1,046 total
includes taxes & fees
Sep 6 - Sep 7
2 bedroom accommodation in East Cowes
A dining area with a table set for four, featuring a bottle of wine, glasses, and a bowl of fruit.

4. The Nautilus -Cowes IOW- 2 bedroom bungalow/garden

The Nautilus -Cowes IOW- 2 bedroom bungalow/garden
Cowes Isle of Wight
10.0 out of 10, Exceptional, (4 reviews)
"Unassuming from the outside, excellently decorated and equipped internally, including a nice garden."
United Kingdom
Simon S.
The price is CA $280
CA $498 total
includes taxes & fees
Sep 13 - Sep 14
The Nautilus -Cowes IOW- 2 bedroom bungalow/garden
A living room with a fireplace, a sofa, a dining table set for two, and a clock on the wall.

5. Luxurious 1-bedroom apartment in wonderful Cowes on the High St near the harbor

Luxurious 1-bedroom apartment in wonderful Cowes on the High St near the harbor
Cowes
10.0 out of 10, Exceptional, (1 review)
"We had a great stay in Alexander Pike’s one bedroom flat in Cowes. The property could not have been situated any better. It was in downtown Cowes on the pedestrian zone. The grocery store and bus stop were directly across the street from the flat. The walk from the ferry was one minute. The apartment was spotless. The appointments were perfect. Everything we could have wanted was provided. We definitely will stay here again when we return to the Isle of Wight."
United States
Steven H.
The price is CA $163
CA $366 total
includes taxes & fees
Sep 6 - Sep 7
Luxurious 1-bedroom apartment in wonderful Cowes on the High St near the harbor
A bedroom with a bed, a wooden bench, a staircase, and a wall-mounted light fixture.

6. Pinnacle Suites

Pinnacle Suites
3.0 star property
Cowes
9.2 out of 10, Wonderful, (40 reviews)
The price is CA $244
CA $293 total
includes taxes & fees
Sep 21 - Sep 22
Pinnacle Suites
A marina with various boats docked, a pier, and a building in the background.

7. Medina by The Solent

Medina by The Solent
2.0 star property
Cowes
9.0 out of 10, Wonderful, (4 reviews)
"Lovely little gem right in the heart of Cowes. 5 mins walk to the Red Jet ferry. Lots of lovely cafés, bars and restaurants within 5 mins. A great find."
United Kingdom
Paul
The price is CA $502
CA $603 total
includes taxes & fees
Sep 12 - Sep 13
Medina by The Solent
A bedroom with a large window, a bed, a grey armchair, and a white door.

8. Cliffhanger, Cowes. Stunning period property with fabulous sea views, sleeps 10

Cliffhanger, Cowes. Stunning period property with fabulous sea views, sleeps 10
Cowes
9.8 out of 10, Exceptional, (66 reviews)
"Really great central place to stay with sea views and amenities all in walking distance."
United States
Patrick H.
The price is CA $1,355
CA $1,549 total
includes taxes & fees
Sep 14 - Sep 15
Cliffhanger, Cowes. Stunning period property with fabulous sea views, sleeps 10
An aerial view of a coastal town with a marina, boats, and surrounding greenery.

9. Stunning property and location with fabulous views overlooking Wootton Creek.

Stunning property and location with fabulous views overlooking Wootton Creek.
Wootton Bridge
10.0 out of 10, Exceptional, (4 reviews)
"very comfortable and cozy cottage, well equipped and fabulous view"
United Kingdom
Rosalind M.
The price is CA $476
CA $476 total
includes taxes & fees
Sep 17 - Sep 18
Stunning property and location with fabulous views overlooking Wootton Creek.
A balcony with a glass railing, a wooden table, and two chairs.

10. Solent Garden

Solent Garden
Cowes
10.0 out of 10, Exceptional, (3 reviews)
"We loved the flat: it was decorated and equipped to a high standard but the high point was sitting on the terrace every evening watching the house martins flying above the garden catching insects on the wing at dusk and then watching small bats doing the same thing as night fell. A very peaceful and restorative holiday home. Label the cutlery draw - it took two of us 3 searches of the kitchen to find it because it fits so seemlessly into the utensils draw!"
United States
Delia
The price is CA $1,313
CA $1,548 total
includes taxes & fees
Sep 18 - Sep 19
Solent Garden
A hammock between trees overlooking a beach with boats and a fence.

11. Cliffside Cosy Cottage by Cowes Beach: 1x KING-Size Double BR & a Twin/Kids BR

Cliffside Cosy Cottage by Cowes Beach: 1x KING-Size Double BR & a Twin/Kids BR
Cowes
10.0 out of 10, Exceptional, (25 reviews)
"Awesome place to stay- we absolutely loved it and will be back"
United Kingdom
Edward
The price is CA $266
CA $300 total
includes taxes & fees
Sep 14 - Sep 15
Cliffside Cosy Cottage by Cowes Beach: 1x KING-Size Double BR & a Twin/Kids BR
A stone manor with a prominent tower, surrounded by a well-maintained lawn and a wooden fence.

12. The Old Abbey Farmhouse

The Old Abbey Farmhouse
Ryde
10.0 out of 10, Exceptional, (28 reviews)
"Everything, the cleanliness, the facilities, the location, the thoughtfulness of the essentials provided"
United States
Gavin
The price is CA $1,265
CA $1,467 total
includes taxes & fees
Sep 17 - Sep 18
The Old Abbey Farmhouse
A beach with a stone tower, a paved walkway, and a clear sky.

13. No 1 Ashey

No 1 Ashey
Ryde
9.4 out of 10, Exceptional, (18 reviews)
"We stayed here for three nights and loved it! The weather was amazing so we made the most out of the pool. The house is very clean and spacious."
United States
Anonymous traveller
The price is CA $1,867
CA $2,242 total
includes taxes & fees
Sep 22 - Sep 23
No 1 Ashey
A modern living room with a wooden floor, a blue sofa, an orange chair, and a small table.

14. Cross Street Apartment

Cross Street Apartment
Ryde
10.0 out of 10, Exceptional, (5 reviews)
"Loved this apartment, it was super comfortable, stylish and clean and the perfect location as it was right next to all the shops and restaurants with a bus stop right outside and the train station and ferries down the road. The company were brilliant with communication and super friendly and we'd definitely return. Loved having the dishwasher and being able to eat in as well as out."
United States
Shona
The price is CA $964
CA $1,135 total
includes taxes & fees
Sep 8 - Sep 9
Cross Street Apartment
A modern bedroom with a large bed, a chair, a window with blinds, and a painting on the wall.

15. Laurel Cottage

Laurel Cottage
Newchurch
10.0 out of 10, Exceptional, (14 reviews)
"Very nice cottage with all the comforts and well placed for visiting the Isle of Wight, near Newport and not far from the coast too."
United States
Jean-Paul
The price is CA $2,277
CA $2,702 total
includes taxes & fees
Sep 22 - Sep 23
Laurel Cottage
A swimming pool with a curved edge, surrounded by a paved area.

16. Rookley Farm Lodge

Rookley Farm Lodge
Rookley
10.0 out of 10, Exceptional, (11 reviews)
"The check in went very well thank you, we’ve had a lovely afternoon in the pool and are looking forward to a good nights sleep :) Thank you so so much"
United States
Sam Jackson
The price is CA $2,409
CA $2,876 total
includes taxes & fees
Sep 4 - Sep 5
Rookley Farm Lodge
A modern two-story house with a tiled roof, large windows, and a small front garden with a potted plant.

17. Creek Lodge

Creek Lodge
2.0 star property
Ryde
10.0 out of 10, Exceptional, (1 review)
"The property is very clean and comfy. We enjoyed our stay and would love to come back!"
United Kingdom
Sok Leng
The price is CA $584
CA $701 total
includes taxes & fees
Sep 4 - Sep 5
Creek Lodge
A room with a large window, a brown sofa, a white table, and a grey wardrobe.

18. The Boat House - Isle of Wight

The Boat House - Isle of Wight
4.0 star property
Seaview
9.0 out of 10, Wonderful, (118 reviews)
"Great location"
United Kingdom
Chloe
The price is CA $251
CA $301 total
includes taxes & fees
Sep 15 - Sep 16
The Boat House - Isle of Wight
A modern kitchen with white cabinets, a wooden countertop, and a built-in sink.

19. Little Lane is a charming, recently refurbished 2 bedroom cottage sleeping 4

Little Lane is a charming, recently refurbished 2 bedroom cottage sleeping 4
Gosport
9.8 out of 10, Exceptional, (6 reviews)
"Enjoyable time in Alverstoke. Great place for a mix of excursions and holiday fun."
Germany
Nadine V.
The price is CA $878
CA $878 total
includes taxes & fees
Sep 4 - Sep 5
Little Lane is a charming, recently refurbished 2 bedroom cottage sleeping 4
A beach with boats, a thatched-roof building, and a view of the sea.

20. Cherry Lodge

Cherry Lodge
Godshill
10.0 out of 10, Exceptional, (13 reviews)
"The excellent accommodation and almost total peace & quiet I will send a separate email re EV charging."
United States
Derick
The price is CA $1,096
CA $1,281 total
includes taxes & fees
Sep 6 - Sep 7
Cherry 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 Whippingham Hotel Reviews

ibis budget Southampton Centre

ibis budget Southampton Centre

8/10 Good
"Friendly & helpful staff Near shopping mall and restaurants"
Lise 1-night trip
Posted 10 hours ago
ibis budget Southampton Centre

Find out more about Whippingham

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 Whippingham. 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.

Frequently asked questions

Can I find vacation rentals in Whippingham?

Yes, there are vacation rentals near top local attractions in Whippingham, or you can go with a more secluded option if you're looking for relaxation.

What's the top vacation rental in Whippingham?

MANOR ON COAST WITH SEA VIEWS, TENNIS COURT, BIG GAMES ROOM + BAR, GARDENS: This vacation home rental near Whippingham is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 12 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Whippingham?

Choose from 3 Expedia vacation rentals in Whippingham for a memorable vacation.

What can I see and do in Whippingham?

While exploring the area, visit family-friendly sights like Isle of Wight Donkey Sanctuary, or get outside and enjoy nature at Isle of Wight Area of Outstanding Natural Beauty. You’ll find favorite places to visit like Southampton Cruise Terminal and New Forest National Park in the larger area.

What are vacation rentals like in Whippingham?

Vacation rentals are private accommodations you can stay in for a couple days or more in Whippingham. Vacation rentals offer extras such as hot tubs, fire pits, and patios so your stay will be comfortable. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for a family trip.