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Our top choices for Winslow holiday rentals

Newpointe Luxury Serviced Apartment at the Atrium

Newpointe Luxury Serviced Apartment at the Atrium
3.5 star property
Milton Keynes
8.0 out of 10, Very good, (6)
"Lovely condition, really cosy and warm - especially as it’s cold at the moment! Parking available on property Convenient location - shops 20 mins walk away "
United Kingdom
Emily
The price is ฿4,548
฿6,927 total
includes taxes & fees
26 Dec - 27 Dec
Newpointe Luxury Serviced Apartment at the Atrium

Escapade Silverstone

Escapade Silverstone
3.0 star property
Towcester
9.8 out of 10, Exceptional, (113)
"Beautiful location, rooms, restaurant, food - everything! Cannot fault it. We loved the wellness area too. So relaxing. "
United Kingdom
Charlotte
The price is ฿5,546
฿6,656 total
includes taxes & fees
4 Jan - 5 Jan 2026
Escapade Silverstone

Shepherdshut-cotswolds-petfriendly-woodburner

Shepherdshut-cotswolds-petfriendly-woodburner
2.0 star property
Brackley
10.0 out of 10, Exceptional, (2)
"Super cute, like being in your own romantic little bubble in the countryside. We came to watch a friend do a parachute jump at the airfield for charity. It was the perfect place to stay for a night or two. Loved the BBQ, the view through the windows and the way the space was designed. So compact and yet everything was so considered and well designed. "
United Kingdom
James
The price is ฿5,365
฿5,365 total
includes taxes & fees
7 Jan - 8 Jan 2026
Shepherdshut-cotswolds-petfriendly-woodburner

Station house

Station house
2.0 star property
Central Milton Keynes
The price is ฿3,946
฿6,204 total
includes taxes & fees
26 Dec - 27 Dec
Station house

The George Inn Hotel Rooms - Room 3

The George Inn Hotel Rooms - Room 3
2.0 star property
Great Missenden
The price is ฿5,378
฿6,454 total
includes taxes & fees
8 Jan - 9 Jan 2026
The George Inn Hotel Rooms - Room 3

Fountain View Cottage

Fountain View Cottage
3.0 star property
Bicester
9.0 out of 10, Wonderful, (4)
"We stayed here as a base for the Game Fair and it was a great location for that. We didn’t really explore the area much but we did get pizza from The Hertford which was good. There wasn’t any garden chairs and is it was lovely weather this was a bit amid a shame as the domino was in the courtyard a fair bit. The cottage was pretty, tidy, clean and cosy. No welcome package was a bit of a shame as this has become pretty standard for holiday cottages and the garden was overrun with bindweed...
United Kingdom
Georgina
The price is ฿19,161
฿22,994 total
includes taxes & fees
2 Jan - 3 Jan 2026
Fountain View Cottage

Salaam Letting

Salaam Letting
3.5 star property
Milton Keynes
Salaam Letting

City Stay Apartments - Vizion

City Stay Apartments - Vizion
3.5 star property
Central Milton Keynes
6.6 out of 10, (9)
"The accommodation was great, however collecting and dropping of keys was a bit faffy as I was on my own. It would be great if you were going as a couple."
United Kingdom
Natalie
The price is ฿6,297
฿7,556 total
includes taxes & fees
8 Jan - 9 Jan 2026
City Stay Apartments - Vizion

Lovely 5BD Home with Cinema & Games Room

Lovely 5BD Home with Cinema & Games Room
2.0 star property
Marsh Gibbon
The price is ฿14,432
฿30,433 total
includes taxes & fees
4 Jan - 5 Jan 2026
Lovely 5BD Home with Cinema & Games Room

PRIVATE ROOMs In TOWN CENTRE FREE PARKING WIFI AND PATIO WITH AA STAY LTD

PRIVATE ROOMs In TOWN CENTRE FREE PARKING WIFI AND PATIO WITH AA STAY LTD
3.5 star property
Aylesbury
6.6 out of 10, (25)
"Dirty window hanging off bathroom I had to clean before using . I am reporting this to health and safety. How do I get a refund. Had to wipe down all surfaces in room.even smelled dirty not fresh"
United Kingdom
Stephen
The price is ฿1,952
฿2,678 total
includes taxes & fees
10 Jan - 11 Jan 2026
PRIVATE ROOMs In TOWN CENTRE FREE PARKING WIFI AND PATIO WITH AA STAY LTD

Swedish Cottages

Swedish Cottages
3.0 star property
Luton
7.2 out of 10, Good, (43)
"We needed somewhere to stay near Luton for one night, this was perfect, easy to find and park, quiet, just on outskirts of town and a good price "
United Kingdom
Nicola
The price is ฿2,974
฿3,568 total
includes taxes & fees
4 Jan - 5 Jan 2026
Swedish Cottages

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)
"Excellent really enjoyed stay. Perfect little getaway for a short break. "
United Kingdom
Peter
The price is ฿6,706
฿8,047 total
includes taxes & fees
30 Dec - 31 Dec
Tring Grange Cottage - Sleeps 2 - Onsite Parking

The George Inn Hotel Rooms

The George Inn Hotel Rooms
2.0 star property
Great Missenden
The price is ฿7,090
฿8,507 total
includes taxes & fees
2 Jan - 3 Jan 2026
The George Inn Hotel Rooms

Kite Cottage

Kite Cottage
3.5 star property
Brackley
The price is ฿18,376
฿22,052 total
includes taxes & fees
8 Jan - 9 Jan 2026
Kite Cottage

Woodland Retreat in High Wycombe

Woodland Retreat in High Wycombe
2.0 star property
High Wycombe
Woodland Retreat in High Wycombe

The Wild Bloom - From 225 Per Night

The Wild Bloom - From 225 Per Night
2.0 star property
Great Missenden
The price is ฿9,792
฿20,466 total
includes taxes & fees
13 Jan - 14 Jan 2026
The Wild Bloom - From 225 Per Night

The Granary

The Granary
3.5 star property
Bedford
The price is ฿22,337
฿26,804 total
includes taxes & fees
30 Dec - 31 Dec
The Granary

Posh Wetheringsett in Milton Keynes

Posh Wetheringsett in Milton Keynes
2.0 star property
Milton Keynes
The price is ฿8,858
฿10,629 total
includes taxes & fees
8 Jan - 9 Jan 2026
Posh Wetheringsett in Milton Keynes

The Angel's Rest

The Angel's Rest
2.0 star property
Milton Keynes
The price is ฿32,720
฿39,265 total
includes taxes & fees
29 Dec - 30 Dec
The Angel's Rest

Yew Tree Farm

Yew Tree Farm
3.0 star property
Aylesbury
The price is ฿106,225
฿127,470 total
includes taxes & fees
29 Dec - 30 Dec
Yew Tree Farm
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 Winslow Hotel Reviews

Find out more about Winslow

Search for holiday rentals in Winslow on Expedia! You can easily find your home rentals, villas, holiday apartments in Winslow using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winslow!

Frequently asked questions

Are there holiday rentals in Winslow?

Yes, there are holiday rentals close to the most popular sights in Winslow, or you can select a more secluded option if you're looking for a relaxing stay. Winslow is known for its cafés and football games. Make sure you have time to check out the churches and entertainment choices during your trip.

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

PRIVATE ROOMs In TOWN CENTRE FREE PARKING WIFI AND PATIO WITH AA STAY LTD: This holiday home rental outside of Winslow is on the boardwalk, and equipped with daily housekeeping and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Winslow?

While exploring the area, visit family-friendly sights like Planet Ice, or get outside and enjoy nature at Bletchley Park. Winslow Farmers Market and St Laurence Church are a couple of places you'll find in the wider area.

What are holiday rentals like in Winslow?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winslow. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.