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St Michaels Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for St Michaels holiday rentals

A wooden deck with a wooden chair and table, a blanket, and breakfast items.

1. Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom

Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
Tenterden
9.0 out of 10, Wonderful, (6 reviews)
"Great little property, surprisingly comfortable for a small space, nice rural views from the lovely hot tub, and great beer from the onsite brewery!"
United States
Harry I.
The price is NZ$431
includes taxes & fees
28 Sept - 29 Sept
Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
A cozy room with a bed, a small table, and a window overlooking a scenic landscape.

2. Songbirds

Songbirds
3.0 star property
Tenterden
10.0 out of 10, Exceptional, (1 review)
"Songbirds was so peaceful and quiet and would definitely go again The hosts were fantastic and very welcoming"
United Kingdom
Jessica
The price is NZ$660
includes taxes & fees
2 Oct - 3 Oct
Songbirds
A wooden deck with two wooden chairs and a table, a hot tub, and a building with a door open to a kitchen area.

3. Challenger - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom

Challenger - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
Tenterden
9.2 out of 10, Wonderful, (11 reviews)
"What a beautiful stay , peaceful , everything you could need for a well needed escape . Staff excellent , surroundings wonderful , bar / restaurant fantastic . Can’t wait to go back ."
United States
Anonymous traveller
The price is NZ$474
includes taxes & fees
29 Sept - 30 Sept
Challenger - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
A wooden cabin with a hot tub, a covered deck, and a sign reading "Cascade."

4. Cascade - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom

Cascade - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
Tenterden
9.8 out of 10, Exceptional, (7 reviews)
"Found this place fairly last minute and couldn’t believe what a little gem it was. Gorgeous surroundings, an oasis of calm. We had a lovely stay."
United States
Anonymous traveller
The price is NZ$474
includes taxes & fees
29 Sept - 30 Sept
Cascade - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
A restaurant interior with wooden tables and chairs, a bar area with a bartender, and a brick wall with framed pictures.

5. Pilgrim - a holiday let that sleeps 2 guests in 1 bedroom

Pilgrim - a holiday let that sleeps 2 guests in 1 bedroom
Tenterden
9.2 out of 10, Wonderful, (5 reviews)
"Has everything you need. Very clean and comfortable. Only problem was the light coming in early in the morning, may want to take a sleep mask with you if you’re a light sleeper. Other thank that could not fault it."
United States
Rebecca J.
The price is NZ$520
includes taxes & fees
29 Sept - 30 Sept
Pilgrim - a holiday let that sleeps 2 guests in 1 bedroom
A cozy interior with a wood-burning stove, a kitchen area, a sofa, and a view of the outdoors.

6. Extraordinary Huts

Extraordinary Huts
3.0 star property
Rye
9.6 out of 10, Exceptional, (45 reviews)
"A stunningly beautiful setting. Clean, tidy and, elegantly decorated and set out. Secure, peaceful and comfortable. We shall most definitely stay there again. Cannot recommend highly enough! ✨💫✨💫✨💫💚🌲💚💫✨💫✨"
United Kingdom
Diana
The price is NZ$345
includes taxes & fees
30 Sept - 1 Oct
Extraordinary Huts
A living room with a sectional sofa, a fireplace, and a TV mounted on the wall.

7. The Pigsty at the Secret Garden

The Pigsty at the Secret Garden
2.0 star property
Ashford
The price is NZ$549
includes taxes & fees
26 Oct - 27 Oct
The Pigsty at the Secret Garden
A covered wooden walkway leading to a building with large glass doors.

8. Birch - Flimwell Park Lodges

Birch - Flimwell Park Lodges
Ticehurst
10.0 out of 10, Exceptional, (1 review)
"very good clean room with excellent bathroom"
United States
james t.
The price is NZ$210
includes taxes & fees
29 Sept - 30 Sept
Birch - Flimwell Park Lodges
A wooden balcony attached to a building with a large tree in the background.

9. A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye

A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye
Rye
10.0 out of 10, Exceptional, (2 reviews)
"A little gem nestled in the countryside with glorious views. Lucy’s apartment was spotlessly clean and tidy, comfortable and very well equipped. Lucy is an absolute hoot- very welcoming and full of suggestions of things to see or do. Perfect for dogs too, with a lovely enclosed garden and lots of walks from the location detailed in the information folder. Lots of lovely pubs nearby too including a local just across the way. We would definitely come back."
United Kingdom
Kerry H.
The price is NZ$303
includes taxes & fees
28 Sept - 29 Sept
A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye
An open door leading to a wooden deck with a view of a green landscape and trees.

10. Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom

Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
Tenterden
9.6 out of 10, Exceptional, (14 reviews)
"This was our first of hopefully many visits and we loved the whole vibe x The bed was so comfortable and we had a wonderful time x"
United States
Anonymous traveller
The price is NZ$474
includes taxes & fees
29 Sept - 30 Sept
Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
A small wooden cabin with a porch, a bench, and a table.

11. The Field View 2 by Tiny Away

The Field View 2 by Tiny Away
Egerton
The price is NZ$352
includes taxes & fees
29 Sept - 30 Sept
The Field View 2 by Tiny Away
A bedroom with a bed, bedside table, nightstand, and a ceiling light fixture.

12. Summerhill by Suspire

Summerhill by Suspire
2.5 star property
Ashford
The price is NZ$422
includes taxes & fees
9 Oct - 10 Oct
Summerhill by Suspire
A modern bedroom with a large bed, a bedside table, a desk, and a window.

13. The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom

The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
Rye
9.8 out of 10, Exceptional, (8 reviews)
"Had a great time, thank you very much ! Would definitely stay again! Good location, easy to get into Rye and surounds."
United States
Anonymous traveller
The price is NZ$474
includes taxes & fees
30 Sept - 1 Oct
The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
A cozy bedroom with a wooden headboard, a bed with patterned pillows, bedside lamps, and a decorative sign on the wall.

14. Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest

Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
East Sussex
10.0 out of 10, Exceptional, (13 reviews)
"Fabulous host. Private cabin, lovely log burner, absolutely magnificent bed ! Shower was great, everything you could need, like milk in the fridge, great coffee etc. lovely view in the morning of the horses, donkey and pony in the fields. Look forward to staying there again !"
United Kingdom
Mark
The price is NZ$330
includes taxes & fees
27 Sept - 28 Sept
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
A bedroom with a bed, a yellow sofa, and a skylight.

15. Kick back and relax in this stylish apartment, 12 mins from Le Shuttle

Kick back and relax in this stylish apartment, 12 mins from Le Shuttle
Mersham
The price is NZ$289
includes taxes & fees
28 Sept - 29 Sept
Kick back and relax in this stylish apartment, 12 mins from Le Shuttle
A mobile home with a front porch, a small attached garage, and a single-story structure.

16. Seashell Cove - 2 bedrooms sleeps 6

Seashell Cove - 2 bedrooms sleeps 6
Dymchurch
The price is NZ$514
includes taxes & fees
28 Sept - 29 Sept
Seashell Cove - 2 bedrooms sleeps 6
A secluded outdoor area with two small, semi-circular wooden structures, surrounded by lush greenery and trees.

17. Chestnut Meadow Camping

Chestnut Meadow Camping
4.0 star property
Bexhill-on-Sea
10.0 out of 10, Exceptional, (5 reviews)
"Really nice stay in lovely cabin."
United Kingdom
Mary
The price is NZ$175
includes taxes & fees
27 Sept - 28 Sept
Chestnut Meadow Camping
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

18. The PigSty at the Secret Garden

The PigSty at the Secret Garden
Biddenden
The price is NZ$562
includes taxes & fees
29 Sept - 30 Sept
The PigSty at the Secret Garden
A house with a prominent moon in the sky, surrounded by trees.

19. Elegant Hideaway The Stanhope

Elegant Hideaway The Stanhope
Doddington
The price is NZ$222
includes taxes & fees
13 Oct - 14 Oct
Elegant Hideaway The Stanhope
A rustic wooden cabin with a covered outdoor seating area, surrounded by lush greenery and a gravel path.

20. Birch Cottage: Starlit Soaks and Wood-Fired Warmth hot tub

Birch Cottage: Starlit Soaks and Wood-Fired Warmth hot tub
maidstone
9.8 out of 10, Exceptional, (9 reviews)
"Wonderful stay we enjoyed seeing in the new year in such a beautiful location, thank you very much"
United Kingdom
Madeline K.
The price is NZ$476
includes taxes & fees
29 Sept - 30 Sept
Birch Cottage: Starlit Soaks and Wood-Fired Warmth hot tub
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 St Michaels Hotel Reviews

Ashford International Hotel & Spa

Ashford International Hotel & Spa

10/10 Excellent
"Plenty of parking and the staff were very informative and professional both in the hotel and spa. The evening meal was nice but expensive in my opinion but breakfast was excellent value for money"
Kevin 1-night trip
Posted 4 hours ago
Ashford International Hotel & Spa

Find out more about St Michaels

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

Frequently asked questions

Are there holiday rentals in St Michaels?

Yes, there are holiday rentals close to the most popular sights in St Michaels, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say St Michaels has a good selection of restaurants. Make sure you have time to check out the golf courses and gardens during your trip.

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

DADIO's Barn - Indoor Swimming Pool 400 Years Old & Hot tub: This holiday home rental outside of St Michaels is located on a lake, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in St Michaels?

Explore the area and family-friendly sights such as Stoneacre, or get out into nature at a spot like High Weald. In the wider area, you’ll find The Chapel Down Winery and Gusbourne Estate Winery.

What’s a holiday rental in St Michaels like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in St Michaels. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips or small group gatherings.