Details

Living room

The Sky Penthouse

9.7 / 10

Outstanding(67 Ratings)

$$$$

Apartment in Winchester

2 guests · 2 bedrooms · 1 bath

Reasons to book

Guests love it hereGuests give this property a top rating

High-end valueWell priced for this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

Location

city location on map

Nearby attractions

Weald & Downland Living Museum

Tapnell Farm Park

Spinnaker Tower

Reviews

9 / 10

Good for family of three or four to stay in Winchester for a week.

Excellent location, very close to high street. Very well equipped kitchen, good if you like to cook. Facilities were well maintained. Owner actively provide information to help us get to the room smoothly. They have washing machines and ironing board.

10 / 10

Very enjoyable break in excellent accommodation. Friendly and informative communication from host.

Excellent location. Spotlessly clean and comfortable accommodation.

Nothing to dislike

9 / 10

Very nice apartment in great location. Excellent very helpful host

close to city centre

10 / 10

First class accommodation in a beautiful city

Spotlessly clean, great location, fantastic views, excellent host with first class pre-check-in information.

Photos

Property building

See all properties

The Sky Penthouse

Top rated by guests

Living room

Property building

Other

Dining area

Dining area

9.7Outstanding

(67 Ratings)

"Excellent location. Spotlessly clean and comfortable accommodation."

Verified guest

Don't miss out! Price and availability may change

9.7 / 10

Outstanding(67 Ratings)

Apartment in Winchester

2 guests · 2 bedrooms · 1 bath

Reasons to book

Guests love it hereGuests give this property a top rating

High-end valueWell priced for this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this apartment rental

Historic Setting

Amenities

Free WiFi/internet

Free Parking

Non-smoking

Gym

Balcony/Terrace

WiFi/Internet

Accessible Parking

Outdoor Cooking

Accessible by lift

Contactless check-in/out

Cleaning products

Map of Winchester

city location on map

Nearby attractions

Weald & Downland Living Museum

Tapnell Farm Park

Spinnaker Tower

Ratings and reviews

9.7 / 10

Outstanding(67 Ratings)

100% verified reviews

9 / 10Outstanding·Sep 2026

Excellent location, very close to high street. Very well equipped kitchen, good if you like to cook. Facilities were well maintained. Owner actively provide information to help us get to the room smoothly. They have washing machines and ironing board.

10 / 10Outstanding·Aug 2026

Excellent location. Spotlessly clean and comfortable accommodation.

Nothing to dislike

9 / 10Outstanding·Jun 2026

close to city centre

10 / 10Outstanding·May 2026

Spotlessly clean, great location, fantastic views, excellent host with first class pre-check-in information.

$$$$

FAQs

Does this property follow enhanced cleaning procedures?

Yes, this apartment has implemented enhanced cleaning procedures and processes to keep you healthy and safe.

Is parking included with this apartment?

Parking is not specified as an available amenity at The Sky Penthouse. For more information, we encourage you to contact the property about where to park.

Is there a pool at this apartment?

We didn’t find pool listed as an amenity for this apartment. It may be worth double checking if a pool is important for your stay.

Is The Sky Penthouse pet friendly?

Unfortunately, this apartment is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at The Sky Penthouse?

We found 11 amenities for this rental. This includes free wifi/internet, free parking, non-smoking, gym, and balcony/terrace.

Explore similar stays in Winchester

Explore all stays

10 / 10

Outstanding(1 Rating)

The Sky Penthouse, City Centre Luxury

4 guests · 2 bedrooms · 1 bath

Experience vacation in Winchester with our Apartment, The Sky Penthouse, City Centre Luxury. Enjoy amenities such as No pets allowed, Family friendly and Non-smoking, and more.

8.6 / 10

Excellent(43 Ratings)

The Old Brewery Boardroom - Winchester City Centre - Unique Property - Free Parking - Sleeps 6 - by Anchored Accommodation

2 guests · 3 bedrooms · 1 bath

Free WiFi/internet · Garden · Smoking allowed

This inviting House in Winchester can fit your needs for many types of vacations, at $369 per night.

Situated moments from High Street & Theatre Royal

Vacation rental

2 guests · 1 bedroom · 1 bath

WiFi/Internet · TV · Coffee/tea maker

This Vacation rental in Winchester, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

Period Home in the Heart of Winchester

6 guests · 4 bedrooms · 2 baths

Looking for a memorable stay in Winchester? Our House might just be what you're looking for. Enjoy amenities including No pets allowed, Family friendly and Non-smoking, and more during your stay.

Stylish 3Bd Townhouse In Central Winchester

4 guests · 3 bedrooms · 3 baths

Garden

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Winchester, at $311 per night for your next great vacation.

9.5 / 10

Outstanding(34 Ratings)

The Nestle House

2 guests · 2 bedrooms · 1 bath

Free WiFi/internet · Balcony/Terrace · Garden

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Winchester, at $340 per night for your next great vacation.

10 / 10

Outstanding(7 Ratings)

The Nestle House City Centre Luxury

4 guests · 2 bedrooms · 1 bath

Looking for a memorable stay in Winchester? Our Cottage might just be what you're looking for. Enjoy amenities including No pets allowed, Family friendly and Non-smoking, and more during your stay.

9.4 / 10

Outstanding(3 Ratings)

Luxury penthouse in Winchester

4 guests · 2 bedrooms · 1 bath

When traveling to Winchester, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $291 per night.

Work Friendly Home

9.4 / 10

Outstanding(19 Ratings)

Designer's Town House

2 guests · 3 bedrooms · 1 bath

Free WiFi/internet · Balcony/Terrace · Garden

Experience the best of Winchester with this House available for $357. This property is equipped with amenities including Free Parking, Tennis court and Golf course (within 2 mi), and more.

9.6 / 10

Outstanding(19 Ratings)

South House offers high comfort self-catering accommodation for up to 6 people,

6 guests · 3 bedrooms · 1 bath

Looking to create some memories in Winchester? Look no further than our House, South House offers high comfort self-catering accommodation for up to 6 people,. Enjoy top-rated amenities including No pets allowed and Non-smoking, and more.

Work Friendly Home

8.5 / 10

Excellent(10 Ratings)

2-Bedroom Stunning, Chic, Spacious & Stylish Retreat, Central Winchester, Free On-Street Parking, Sleeps 6, Pet-Friendly - by Blue Puffin Stays

2 guests · 2 bedrooms · 1 bath

Free WiFi/internet · Balcony/Terrace · Garden

This House in Winchester, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

Stylish 3Bd Townhouse In Central Winchester

4 guests · 3 bedrooms · 3 baths

Garden

House in Winchester, for $311 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

You can save with One Key

Period Home in the Heart of Winchester

6 guests · 4 bedrooms · 2 baths

Business stays, family stays, couples stay, getaway vacation, and rental in Winchester at Period Home in the Heart of Winchester for $373 for your next trip.

8.9 / 10

Excellent(21 Ratings)

Stylish 3BD Townhouse in Central Winchester

2 guests · 3 bedrooms · 3 baths

Free WiFi/internet

The best choice in Winchester for House, for $379 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

10 / 10

Outstanding(2 Ratings)

Chic Home w/ Garden & Free On-Street Parking

6 guests · 2 bedrooms · 1 bath

Enjoy the best of Winchester in our House, Chic Home w/ Garden & Free On-Street Parking. A stunning property with amenities including Pets allowed, Family friendly and Non-smoking, and more.

You can save with One Key

10 / 10

Outstanding(7 Ratings)

Stunning House in Central Winchester

4 guests · 2 bedrooms · 1 bath

Business stays, family stays, couples stay, getaway vacation, and rental in Winchester at Stunning House in Central Winchester for $367 for your next trip.

8.5 / 10

Excellent(24 Ratings)

Central Chic 3 bed, Great Location

2 guests · 3 bedrooms · 2 baths

Free WiFi/internet

Looking for a memorable stay in Winchester? Our Apartment might just be what you're looking for. Enjoy amenities including Free Parking, Non-smoking and Family friendly, and more during your stay.

New to VacationRenter

Clifton Lodge

4 guests · 1 bedroom · 1 bath

Free WiFi/internet · Kitchen · Kitchenware

This Cottage for $317 in Winchester, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

Work Friendly Home

8.2 / 10

Excellent(17 Ratings)

2-Bedroom Stylish & Gorgeous, Cosy Westgate Cottage Retreat, Central Winchester, Free On-Street Parking Permit, with Garden, Close to Cathedral - Sleeps 6, Pets are Welcome - by Blue Puffin Stays

2 guests · 2 bedrooms · 1 bath

Free WiFi/internet · Garden · Ironing facilities

Enjoy the best of Winchester in our House, 2-Bedroom Stylish & Gorgeous, Cosy Westgate Cottage Retreat, Central Winchester, Free On-Street Parking Permit, with Garden, Close to Cathedral - Sleeps 6, Pets are Welcome - by Blue Puffin Stays. A stunning property with amenities including Free Parking, Pets allowed and Golf course (within 2 mi), and more.

You can save with One Key

10 / 10

Outstanding(2 Ratings)

Chic Home w/ Garden & Free On-Street Parking

6 guests · 2 bedrooms · 1 bath

Discover the beauty of Winchester with a stay at Chic Home w/ Garden & Free On-Street Parking, a top rated House with amenities such as Pets allowed, Family friendly and Non-smoking, and more.

9.6 / 10

Outstanding(5 Ratings)

2 bedroom accommodation in Winchester

4 guests · 2 bedrooms · 1 bath

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Winchester, at $392 per night for your next great vacation.

10 / 10

Outstanding(1 Rating)

Comfortable Ground Floor Apartment with Parking

2 guests · 2 bedrooms · 1 bath

Free WiFi/internet · Balcony/Terrace

Experience vacation in Winchester with our Apartment, Comfortable Ground Floor Apartment with Parking. Enjoy amenities such as Free Parking, Balcony/Terrace and WiFi/Internet, and more.

You can save with One Key

9.6 / 10

Outstanding(5 Ratings)

2 bedroom accommodation in Winchester

4 guests · 2 bedrooms · 1 bath

This Cottage in Winchester, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

8 / 10

Excellent(2 Ratings)

Lovely 2BR Cottage Spacious with Garden

5 guests · 2 bedrooms · 1 bath

Soak up the beauty of Winchester in our House, Lovely 2BR Cottage Spacious with Garden. With a range of amenities such as Pets allowed, Family friendly and Non-smoking, you'll feel right at home.

Work Friendly Home

9.4 / 10

Outstanding(73 Ratings)

4 Bed City House with Private Garden and Parking

2 guests · 4 bedrooms · 3 baths

Free WiFi/internet · Garden

This attractive House in Winchester, $407 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

Clifton Lodge

2 guests · 2 bedrooms · 1 bath

Free WiFi/internet

The best choice in Winchester for Apartment, for $372 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

You can save with One Key

10 / 10

Outstanding(12 Ratings)

4 Bed City House With Private Garden and Parking

7 guests · 4 bedrooms · 3 baths

The best choice in Winchester for House, for $420 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

10 / 10

Outstanding(6 Ratings)

2 bedroom accommodation in Winchester

2 guests · 2 bedrooms · 2 baths

Soak up the beauty of Winchester in our Cottage, 2 bedroom accommodation in Winchester. With a range of amenities such as No pets allowed, Family friendly and Non-smoking, you'll feel right at home.

9.8 / 10

Outstanding(16 Ratings)

Mallard Cottage

2 guests · 2 bedrooms · 2 baths

Free WiFi/internet · Garden

This inviting House in Winchester can fit your needs for many types of vacations, at $387 per night.

You can save with One Key

10 / 10

Outstanding(6 Ratings)

2 bedroom accommodation in Winchester

2 guests · 2 bedrooms · 2 baths

This Cottage in Winchester, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

Winchester travel inspiration

The Best American Lake Town Awards 2026: Where Shoreline Meets Soul

America’s Best Hidden Beach Towns (2026 Awards)

Best Small Towns for Spring Getaways (2026)

The Ultimate Packing List For Your Vacation (2026)

Where Everyone Knows Your Name: America’s Most Welcoming Small Towns (2026)

35 Road Trip Necessities for the Perfect Journey

How to Pack a Suitcase: 12 Steps to Perfect Packing

Top 25 Packing Tips for 2026 (Smarter, Lighter, Stress-Free Travel)

Keep exploring