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Penn Holiday Rentals

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Our top choices for Penn holiday rentals

1. A lovely couples retreat in the heart of the Chilterns.

A lovely couples retreat in the heart of the Chilterns.
Penn
8.4 out of 10, Very good, (7 reviews)
"Was.nice and clean and lovely location "
United Kingdom
Gavin S.
The price is NZ$515
includes taxes & fees
11 Oct - 12 Oct
A lovely couples retreat in the heart of the Chilterns.

2. Buckingham Apartments

Buckingham Apartments
3.0 star property
High Wycombe
7.2 out of 10, Good, (19 reviews)
"This hotel is not as advertised or as described - be warned "
United Kingdom
Alexandra
The price is NZ$240
includes taxes & fees
12 Oct - 13 Oct
Buckingham Apartments

3. High Wycombe Apartments

High Wycombe Apartments
2.0 star property
High Wycombe
The price is NZ$240
includes taxes & fees
11 Oct - 12 Oct
High Wycombe Apartments

4. Beautiful 1-bed Studio in Bourne end

Beautiful 1-bed Studio in Bourne end
3.0 star property
Bourne End
10.0 out of 10, Exceptional, (2 reviews)
"Super stay, gorgeous studio with separate kitchen and bathroom, immaculate throughout. Very convenient for the train station and a beautiful walk by the Thames is just a few minutes away! "
United Kingdom
natalie
The price is NZ$238
includes taxes & fees
24 Oct - 25 Oct
Beautiful 1-bed Studio in Bourne end

5. Heathrow Windsor Apart Hotel

Heathrow Windsor Apart Hotel
2.0 star property
Colnbrook
6.8 out of 10, (9 reviews)
"Beautiful place!"
United States
Jennifer
The price is NZ$233
includes taxes & fees
11 Oct - 12 Oct
Heathrow Windsor Apart Hotel

6. Livin’ Serviced Apartments

Livin’ Serviced Apartments
4.0 star property
Watford
9.0 out of 10, Wonderful, (359 reviews)
"Room were very clean"
United Kingdom
Yuen yee
The price is NZ$191
includes taxes & fees
15 Oct - 16 Oct
Livin’ Serviced Apartments

7. The Fox at Hurley - Delightful Property!

The Fox at Hurley - Delightful Property!
Maidenhead
The price is NZ$347
includes taxes & fees
12 Oct - 13 Oct
The Fox at Hurley - Delightful Property!

8. Copper Castle & Petting Farm near Legoland

Copper Castle & Petting Farm near Legoland
4.0 star property
Windsor
10.0 out of 10, Exceptional, (5 reviews)
"The copper castle was an amazing place to stay, clean, comfortable, staff were amazing, children loved the animals and collecting egg's from the chickens in the morning. Owner's were very helpful and accommodating, will definitely be coming back for another stay."
United Kingdom
Susan
The price is NZ$374
includes taxes & fees
11 Oct - 12 Oct
Copper Castle & Petting Farm near Legoland

9. Willow Court Farm

Willow Court Farm
4.0 star property
Windsor
10.0 out of 10, Exceptional, (216 reviews)
"Very nice, comfortable room, nice to have the kitchen. Lots of space outside to eat and relax! The kids loved the animals and that it’s clise to Legoland! The restaurant near by was really nice too and also easy to get around without a car."
Canada
Anne
The price is NZ$354
includes taxes & fees
11 Oct - 12 Oct
Willow Court Farm

10. Spacious, light apartment sleeps up to four

Spacious, light apartment sleeps up to four
Cookham
9.6 out of 10, Exceptional, (19 reviews)
"Beautifully refurbished property with very helpful hosts."
United Kingdom
Alexandra C.
The price is NZ$489
includes taxes & fees
13 Oct - 14 Oct
Spacious, light apartment sleeps up to four

11. Grace`s Guesthouse Room 2

Grace`s Guesthouse Room 2
Tring
10.0 out of 10, Exceptional, (4 reviews)
"Brilliant stay"
United Kingdom
Charlotte E.
The price is NZ$240
includes taxes & fees
11 Oct - 12 Oct
Grace`s Guesthouse Room 2

12. Lovely cottage in the heart of the picturesque village of Cookham

Lovely cottage in the heart of the picturesque village of Cookham
Cookham
10.0 out of 10, Exceptional, (1 review)
"Roseleigh Cottage is a lovely little house. It is ideally situated in central Cookham a stones throw from the Thames tow path and close to a range of pubs and other places to eat. The cottage is very well equipped and comfortable. We really enjoyed our stay as did our dog who appreciated the many walks thereabouts."
United States
Maggie L.
The price is NZ$549
includes taxes & fees
14 Oct - 15 Oct
Lovely cottage in the heart of the picturesque village of Cookham

13. Hampden Apartments - The William

Hampden Apartments - The William
3.0 star property
Eton
9.0 out of 10, Wonderful, (20 reviews)
"Always a lovely place to stay "
United Kingdom
Tony
The price is NZ$278
includes taxes & fees
13 Oct - 14 Oct
Hampden Apartments - The William

14. Tring Grange Cottage - Sleeps 2 - Onsite Parking

Tring Grange Cottage - Sleeps 2 - Onsite Parking
3.0 star property
Tring
10.0 out of 10, Exceptional, (2 reviews)
"Excellent really enjoyed stay. Perfect little getaway for a short break. "
United Kingdom
Peter
The price is NZ$421
includes taxes & fees
11 Oct - 12 Oct
Tring Grange Cottage - Sleeps 2 - Onsite Parking

15. Hampden Apartments - The Louis

Hampden Apartments - The Louis
3.0 star property
Eton
9.8 out of 10, Exceptional, (14 reviews)
"Great location especially having free parking. The apartment was very clean and modern."
United Kingdom
Lucy
Hampden Apartments - The Louis

16. The Bluebird - Beautiful one bedroom apartment in Watford

The Bluebird - Beautiful one bedroom apartment in Watford
Garston
9.8 out of 10, Exceptional, (8 reviews)
"We stayed for three nights in October half term. The goat was in a lovely quiet location just a short distance from Harry Potter world. Everything we needed for an easy stay, comfortable beds, quiet neighbours."
United Kingdom
Charlotte R.
The Bluebird - Beautiful one bedroom apartment in Watford

17. 1 bedroom accommodation in Great Missenden

1 bedroom accommodation in Great Missenden
Great Missenden
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location and accommodation - with lovely ‘touches’ left by the host. One of the best places we’ve ever stayed at. Very ‘high end’ finishes and appliances.Host was very friendly and went out of her way to make sure we had everything we needed.Happy to highly recommended."
United Kingdom
David H.
The price is NZ$715
includes taxes & fees
18 Oct - 19 Oct
1 bedroom accommodation in Great Missenden

18. Cosy Cabin Close to Heathrow Airport, Windsor Castle, Legoland, Thorpe Park

Cosy Cabin Close to Heathrow Airport, Windsor Castle, Legoland, Thorpe Park
Horton
10.0 out of 10, Exceptional, (1 review)
"What a beautiful gem this place is. Absolutely wonderful.So clean and well equipped ..... cosy too.Transport excellent. Bus at end of road straight into Heathrow and the London underground.Easy walk to train station to visit London or Windsor.15 minute drive to Legoland or Thorpe Park. Will definitely stay again with the kids! "
United Kingdom
Bruce S.
The price is NZ$332
includes taxes & fees
22 Oct - 23 Oct
Cosy Cabin Close to Heathrow Airport, Windsor Castle, Legoland, Thorpe Park

19. Hampden Apartments - the Diana

Hampden Apartments - the Diana
4.0 star property
Windsor City Centre
9.2 out of 10, Wonderful, (47 reviews)
"Handy for town centre and offers parking which is a must in Windsor .as a big tourist attraction parking is quickly taken up and expensive .apartment has all amenities and spotlessly clean"
United Kingdom
Colin
The price is NZ$288
includes taxes & fees
11 Oct - 12 Oct
Hampden Apartments - the Diana

20. Entire Place | Own Entrance | Kitchen | Garden | WiFi | Walk to Tube | Parking

Entire Place | Own Entrance | Kitchen | Garden | WiFi | Walk to Tube | Parking
Pinner South
9.6 out of 10, Exceptional, (103 reviews)
"It was easy to catch the train quickly. The station was a short walk. The area is lovely & mostly quiet & calm."
United States
Gina K.
The price is NZ$392
includes taxes & fees
11 Oct - 12 Oct
Entire Place | Own Entrance | Kitchen | Garden | WiFi | Walk to Tube | Parking
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 Penn Hotel Reviews

Find out more about Penn

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 Penn 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 Penn. 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 Penn. Seeing all the best attractions is bound to make you fall in love with Penn. 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 Penn short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Penn?

Yes, you can find holiday rentals where you'll be only 11.3 mi (18.2 km) from Warner Bros. Studio Tour London, giving you a secluded option if you'd like a quiet spot to stay.

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

3 Bed House Sleeps 5 - Parking, Garden, Pets: This holiday home rental outside of Penn offers a garden and free WiFi to help you feel comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What can I see and do in Penn?

While exploring the area, visit family-friendly sights like Warner Bros. Studio Tour London, or get outside and enjoy nature at Chiltern Hills. Wycombe Swan Theatre and Hughenden Manor are a couple of places you'll find in the wider area.

What are holiday rentals like in Penn?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Penn. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.