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Winslow Holiday Rentals

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Our top choices for Winslow holiday rentals

Cottage in Luton

Swedish Cottages
3.0 star property
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 AU$171
includes taxes & fees
27 Dec - 28 Dec
Swedish Cottages

Apartment in Towcester

Escapade Silverstone
3.0 star property
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 AU$291
includes taxes & fees
4 Jan - 5 Jan 2026
Escapade Silverstone
8.6 out of 10, Excellent, (8)
"This stylish Annex has everything you need for a comfortable stay"
United Kingdom
Joan
The price is AU$124
includes taxes & fees
1 Jan - 2 Jan 2026
Self-Contained Annex Peaceful Village Setting with Fields Behind. Pet friendly!

Apartment in Tring

Grace`s Guesthouse Room 5
10.0 out of 10, Exceptional, (1)
"This ws a one night stay for business. The property is undergoing renovation currently (sept 25), but my bedroom was extremely lovely. Very spacious, immaculate bathroom - I felt like I was the first person to stay on the room since it has been renovated!Very reasonable, comfortable, lovely bed. In such a great area too, lots of cute cafes, independent restaurants. Tring is so lovely too. I would definitely stay here again. "
United Kingdom
Victoria H.
The price is AU$161
includes taxes & fees
4 Jan - 5 Jan 2026
Grace`s Guesthouse Room 5
2.0 star property
10.0 out of 10, Exceptional, (1)
"Lovely hut, with a peaceful and cosy atmosphere. We stayed here for a couple of nights for the end part of our road trip, whilst visiting around cities and towns, it was great, it was nice and secluded too. "
United Kingdom
Megan-Rose
Shepherdshut-cotswolds-petfriendly-woodburner
10.0 out of 10, Exceptional, (1)
The price is AU$327
includes taxes & fees
28 Dec - 29 Dec
Luxurious & Spacious 2 bed Apartment in Milton Keynes

Apartment in Central Milton Keynes

Station house
2.0 star property
The price is AU$275
includes taxes & fees
2 Jan - 3 Jan 2026
Station house
10.0 out of 10, Exceptional, (1)
"Lovely apartment with great facilities. Great location for food, shopping and entertainment. I would definitely stay again. Good information and access to the apartment from host."
United Kingdom
Donna C.
The price is AU$282
includes taxes & fees
28 Dec - 29 Dec
Modern 2 Bedroom Apartment, Bicester Town Centre

Holiday Home in Luton

Instant Home
10.0 out of 10, Exceptional, (1)
"We stayed for 4 days for a family wedding and get together. Mr Zahid was very wellcoming and helpful host.Accommodation is very spacious and clean. Front drive is big enough to park 2 cars.Overall very happy with the stay. Definitely recommend. "
United Kingdom
Saraj U.
The price is AU$345
includes taxes & fees
2 Jan - 3 Jan 2026
Instant Home
10.0 out of 10, Exceptional, (2)
"Clean, comfortable, well situated, wel equipped. "
United Kingdom
Angela J.
The price is AU$259
includes taxes & fees
1 Jan - 2 Jan 2026
Milton Keynes Luxury Massage Apartment
3.5 star property
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 AU$333
includes taxes & fees
26 Dec - 27 Dec
Newpointe Luxury Serviced Apartment at the Atrium
10.0 out of 10, Exceptional, (3)
"This place was amazing. It has been lovingly converted into accommodation with so much attention to detail that you don’t want to leave. The additional Christmas decorations were super cute and appreciated as well as the full service kitchen (with coffee and milk), games and fabulous top floor 360°window to watch the sunrise/sunset, wildlife etc. Highly recommend a stay here. "
United Kingdom
Tracy
The price is AU$750
includes taxes & fees
1 Jan - 2 Jan 2026
The Windmill Blackthorn Hill - a windmill that sleeps 4 guests in 2 bedrooms
The price is AU$187
includes taxes & fees
28 Dec - 29 Dec
Cozy Detached Studio Retreat with Kitchen & Bath
10.0 out of 10, Exceptional, (1)
"We stayed for one night and loved it! The apartment is new, spotless, and in an excellent location. We really appreciated the free parking, as well as the thoughtful touches like tea, coffee, and all the kitchen utensils we needed. The beds were very comfortable, which made for a good night’s sleep. Our only suggestion would be to have a few extra pillows, but overall it was a wonderful stay and we’d happily come back!"
United Kingdom
Salma
The price is AU$423
includes taxes & fees
30 Dec - 31 Dec
Homely Retreat Spacious Ground Floor Flat Near Oxford City Centre, Free Parking
2.0 star property
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 AU$258
includes taxes & fees
5 Jan - 6 Jan 2026
Shepherdshut-cotswolds-petfriendly-woodburner

Cottage in Bicester

Fountain View Cottage
3.0 star property
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 AU$1,104
includes taxes & fees
2 Jan - 3 Jan 2026
Fountain View Cottage
10.0 out of 10, Exceptional, (1)
"The property was clean, everything we needed to make our stay comfortable was available. The hostess is amazing! 1 in a million. She was available at the end of a phone. She decorated the front room with a happy birthday banner and balloons and made me feel very special. Amaz"
United Kingdom
Elizabeth P.
The price is AU$341
includes taxes & fees
30 Dec - 31 Dec
Charming 3-bedroom house 8 min away from Luton station, Mall and Luton Airport
The price is AU$188
includes taxes & fees
31 Dec - 1 Jan 2026
A light spacious room,with sofa and single bed. Private bathroom with shower.
10.0 out of 10, Exceptional, (1)
"Helpful"
United Kingdom
Daniel
The price is AU$174
includes taxes & fees
28 Dec - 29 Dec
Bicester Court Lodge The Heritage Room | Bicester Holiday Let | 1 Beds & Sleeps 2

Apartment in Central Milton Keynes

Central M K 2-Bedroom Apartment, Sleeps 4, Parking
10.0 out of 10, Exceptional, (1)
"A lovely apartment in a great location. Staff who met us were friendly and helpful. Would highly recommend and we would stay here again if in the area. "
United Kingdom
Elaine S.
The price is AU$300
includes taxes & fees
29 Dec - 30 Dec
Central M K 2-Bedroom Apartment, Sleeps 4, 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 Winslow Hotel Reviews

Find out more about Winslow

Everything you need to know about Winslow holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winslow holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winslow holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winslow holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winslow. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winslow holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winslow holiday rentals we have selected for you start as low as AU$129 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winslow rentals

At Expedia, we put the best Winslow holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winslow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winslow holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winslow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.