Vacation rentals in Whippingham

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Top-rated vacation rentals in Whippingham

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Top guest favorite

The exterior of the barn features a mix of natural stone and brick, illuminated by warm outdoor lighting. A woven willow screen offers privacy, surrounding the well-maintained garden that extends alongside the structure.

Barn in Isle of Wight

Chapel Road Barn, I.O.W Ferry discount available

Chapel Road Barn is a lovingly restored Victorian out-building which is an ideal place for a couple to stay whilst exploring the Isle of Wight. Beautifully furnished and cozy.... We are a 5 minute drive from the car ferry or a 25 minute walk to Ryde Pier. The number 9 bus stop is 2 minutes away and we have a variety of country walks and lovely cycles on hand....... We have partnered with both Red Funnel and Atlas ferries to offer generaous ferry discounts from both Portsmouth and Southampton

ValueLocationHeating

4.97 out of 5 average rating, 323 reviews

Guest favorite

Home in Isle of Wight

Cowes Cottage

A cosy two-bedroom terrace cottage in the heart of Cowes, perfect for up to four guests. Recently renovated, it features a wood-burning stove, a comfortable living area, and a private garden. The cottage has two bedrooms and a well-equipped kitchen. Its narrow layout and steep staircases give it plenty of character, but mean it’s not suitable for toddlers or those with limited mobility On-street parking is available. 5 min walk from West Cowes, Red Jet Hi-Speed catamaran service from Southampton

FamilyLocationAccuracy

4.97 out of 5 average rating, 33 reviews

Guest favorite

A modern kitchen features sleek cabinetry and a stylish backsplash, with ample counter space for meal preparation. A gas hob and electric oven are visible, along with a breakfast bar for two. Natural light enters through a window, enhancing the inviting atmosphere.

Guesthouse in Isle of Wight

Cosy Self Catering Annex 1 Bedroom

⛴️ 0.4 miles from the ferry, Castle Copse Annexe is a lovely compact modern self catering property situated in a quiet housing estate and named after the small copse, a few minutes walk away. Walk through the copse, and it will lead you to the town centre, where you will find shops, cafe's, pharmacies, and supermarkets. It is a 10 minute walk to the beach & crossing to Cowes. The annexe is only suitable for a max of 2 persons and unsuitable for small children due to the stairs, & sofa layout.

LocationValueParking

4.93 out of 5 average rating, 149 reviews

Guest favorite

The image depicts a wooden deck extending over calm water, framed by sleek black railings. In the background, trees display autumn foliage, and a sailboat is anchored nearby, reflecting lightly on the water's surface.

Houseboat in Wooton

Unique creekside floating home with adjacent cabin

A rare opportunity to rent this truly unique waterside property! Rena Haus is a floating home on Wootton Creek, a tidal creek off the Solent, home to much sealife including beautiful swans that swim by on a daily basis as well as breathtaking views on your doorstep. The property comprises Rena Haus on the water and Rena Sommerhaus, a self contained cabin set back from the water with it's own bathroom and facilities. A true tranquil retreat and only 10 minutes from the Fishbourne ferry terminal

ValueFamilyTV

4.89 out of 5 average rating, 375 reviews

Guest favorite

Home in Isle of Wight

Red Brick Haven 5Bed 2Bath for Memorable Reunions

Welcome to this comfortable 5-bedroom house at Cadets Walk on the Isle of Wight, an excellent base for up to 10 guests visiting for family holidays, group trips, business, or a relaxing getaway. Located in a convenient area of the Isle of Wight, this spacious home offers a comfortable base for families, friends, and larger groups looking for a convenient place to stay. With five bedrooms, two bathrooms, and accommodation across the ground floor and first floor, it is ideal for up to 10 guests.

LocationFamilyIndoor spaces

4.9 out of 5 average rating, 21 reviews

Top guest favorite

A private patio area is depicted, featuring a small round table and two chairs. The space is surrounded by brick borders and is paved with light-colored tiles. The entrance to the cottage is showcased, with double doors framed by windows, and greenery visible in the background.

Cottage in Isle of Wight

Albert’s Dairy Cottage, Whippingham

Albert’s Dairy Cottage is a beautifully converted one bedroom cottage situated adjacent to open countryside. The contemporary design offers spacious accommodation, is finished to a high specification and offers the perfect environment for couples looking for a relaxing break away. Conveniently situated less than 10 mins from both the Red funnel and Wightlink car ferry terminals, the property is ideally located for exploring the Island, is close to the River Medina and popular waterside pubs.

FamilyValueHeating

4.96 out of 5 average rating, 214 reviews

Top guest favorite

Home in Isle of Wight

Stone Cottage - Cosy-Dog Friendly-Parking-Cowes

New to the holiday market, Stone Cottage is snug, homely & filled with natural light - all within a 7 minute walk to Cowes Town Centre, RedJet and the sailing community. The light filled lounge with a sinkable sofa and an electric fire gives a nice cosy atmosphere. A stylish & well equipped kitchen with a drop down table & 3 stools. Upstairs are 2 restful bedrooms, a king sized bed in one and a single in the other with space for your travel cot. A ground floor bathroom. Off road parking.

LocationFamilyAccuracy

4.94 out of 5 average rating, 35 reviews

Guest favorite

A cozy lounge area features a navy blue sofa with decorative cushions, complemented by a light rug. In the background, a fully equipped kitchen can be seen. A spiral staircase, showcasing intricate metalwork, ascends to the upper level of the cottage.

Cottage in Isle of Wight

Harbour Cottage Your Romantic Getaway in Cowes

Harbour Cottage - perfect romantic getaway. Close to the centre of vibrant Cowes with local independent shops, cafes, restaurants and marinas. You can leave the car at home! Minutes from Red Jet terminal, floating bridge and Shepards Marina. Generous ferry discounts enquire on booking Harbour Cottage is great for short breaks, or longer stays. Fully fitted kitchen, lounge, conservatory, bathroom and bedroom with king size bed and small sofa fold out ideal for child or small adult only

FamilyLocationOutdoor spaces

4.89 out of 5 average rating, 199 reviews

Top guest favorite

A charming vintage cottage is set amidst lush greenery, featuring a slate roof and blue exterior. The structure is accented by white trim and has a welcoming porch with large windows, allowing natural light to filter inside.

Cottage in Gurnard

A charming little wooden house by the sea

This quirky attractive vintage little cottage is perfect for getting away from it all and relaxing in idyllic surroundings. Just a few metres from the lovely pebbly Gurnard beach, this fully refurbished historical little wooden building is set back from the road and tucked away behind our wild garden. It is accessed from its own car parking space via a little path. At the rear, a small stream goes to the sea and a large oak tree provides shelter to birds and a relaxing swing seat.

FamilyValueLayout

4.96 out of 5 average rating, 299 reviews

Guest favorite

A view from the window captures the tranquil scene of Cowes Harbour with boats gently bobbing in the water. Lush green grass and a well-maintained garden are visible in the foreground, with a distant shoreline lined by trees and buildings.

Cottage in Isle of Wight

Cozy cottage with sea views and off street parking

Built in 1882, our lovely cottage is a former coastguard cottage located in a row of 14. The inside of the cottage is very well appointed and very cozy. The west facing garden deck provides a good size outdoor area to sit and take in the fantastic views of Cowes harbour, the Solent beyond and the amazing sunsets. You will have access to a dedicated off street parking space. Two bedrooms - one with a double bed and one which can be made with two single beds or one king size.

FamilyLocationGrill

4.97 out of 5 average rating, 152 reviews

Top guest favorite

The Watch House is viewed from a garden path lined with blooming flowers, leading down to the beach. The white exterior of the cottage is highlighted against a clear blue sky, while the tide is low, revealing a sandy shore.

Home in Lepe

Iconic Beach Front Stay | The Watch House, Lepe

A standout seafront landmark on Lepe Beach, The Watch House is a lovingly restored former lifeboat and coastguard station, once used to combat smuggling across the Solent. With original features, a modern kitchen, wood burner, cosy window seat over the water, and views to the Isle of Wight, it’s a guest favourite—“an iconic beachfront stay” and “perfect relaxing getaway.” Pet-friendly with parking for two, perfect for families, couples, or friends.

ValueFamilyIndoor spaces

4.98 out of 5 average rating, 154 reviews

Top guest favorite

Cabin in Isle of Wight

Field View Cabin

This stylish modern place to stay is perfect for a great getaway. The cabin is situated on the owners property, set back from a main road. However it has its own separate/private entrance and parking. The Cabin is designed so that the accommodation windows and private patio/sitting area all face the fields. Located centrally on the Island, less than 1 minute walk to bus access and also a short walk to river-side cycle track.

LocationFamilyBeach

4.99 out of 5 average rating, 176 reviews