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St Michaels Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for St Michaels vacation rentals

A hot tub with a wooden deck and a window overlooking a deck area.

1. 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 CA $417
CA $417 total
includes taxes & fees
Oct 27 - Oct 28
Pilgrim - a holiday let that sleeps 2 guests in 1 bedroom
An open door leading to a wooden deck with a view of a green landscape and trees.

2. 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 CA $381
CA $381 total
includes taxes & fees
Oct 27 - Oct 28
Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
A wooden deck with a wooden chair and table, a blanket, and breakfast items.

3. 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 CA $346
CA $346 total
includes taxes & fees
Oct 26 - Oct 27
Ernest - a holiday let by Bloom Stays that sleeps 2 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 CA $381
CA $381 total
includes taxes & fees
Oct 27 - Oct 28
Cascade - a holiday let by Bloom Stays 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.

5. 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 CA $277
CA $277 total
includes taxes & fees
Oct 27 - Oct 28
Extraordinary Huts
A compact kitchen with a window, a kettle, a bottle, a cutting board, and a sink.

6. The Field View 2 by Tiny Away

The Field View 2 by Tiny Away
Egerton
The price is CA $127
CA $193 total
includes taxes & fees
Oct 26 - Oct 27
The Field View 2 by Tiny Away
A horse behind a wooden fence with trees in the background.

7. The Pigsty at the Secret Garden

The Pigsty at the Secret Garden
2.0 star property
Ashford
The Pigsty at the Secret Garden
A modern bedroom with a large bed, a bedside table, a desk, and a window.

8. 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 CA $381
CA $381 total
includes taxes & fees
Oct 26 - Oct 27
The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
A cozy living room with a sofa, a white furry chair, a wooden table, and a fireplace.

9. Pinewood Camping Pods - At Port Lympne Reserve

Pinewood Camping Pods - At Port Lympne Reserve
2.0 star property
Hythe
9.6 out of 10, Exceptional, (40 reviews)
"Wonderful experience and accommodation"
United Kingdom
Lesley
The price is CA $226
CA $271 total
includes taxes & fees
Nov 2 - Nov 3
Pinewood Camping Pods - At Port Lympne Reserve
A bedroom with a bed, pillows, a headboard, two wall-mounted lamps, and a window with a view of trees.

10. 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 CA $196
CA $265 total
includes taxes & fees
Oct 26 - Oct 27
A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye
A wooden deck with two wooden chairs and a table, a hot tub, and a building with a door open to a kitchen area.

11. 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 CA $381
CA $381 total
includes taxes & fees
Oct 26 - Oct 27
Challenger - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
A rustic wooden cabin with a covered outdoor seating area, surrounded by lush greenery and a gravel path.

12. 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, (10 reviews)
"Lovely property with a great location, a 5 minute drive from Leeds Castle! Very friendly host and accompanying doggie! Both properties also had great wood burner hot tubs which were fantastic."
United Kingdom
Samuel
The price is CA $281
CA $386 total
includes taxes & fees
Oct 28 - Oct 29
Birch Cottage: Starlit Soaks and Wood-Fired Warmth hot tub
A brick house with a large open doorway leading to a dining area.

13. Vine Cottage

Vine Cottage
3.5 star property
Tenterden
The price is CA $793
CA $951 total
includes taxes & fees
Nov 13 - Nov 14
Vine Cottage
A bedroom with a bed, a window, a chair, and a small table.

14. Charming 2-Bed Cottage near Bodiam Castle, Rye & Camber Sands

Charming 2-Bed Cottage near Bodiam Castle, Rye & Camber Sands
Hawkhurst
The price is CA $185
CA $330 total
includes taxes & fees
Nov 1 - Nov 2
Charming 2-Bed Cottage near Bodiam Castle, Rye & Camber Sands
A cozy living room with a fireplace, a television, and a collection of books and DVDs on a table.

15. An unusual two-storey apartment with beams and an open fire.

An unusual two-storey apartment with beams and an open fire.
Rye
10.0 out of 10, Exceptional, (11 reviews)
"Lovely little flat enjoyed the central location of the flat would definitely recommend "
United States
Robert E.
The price is CA $369
CA $369 total
includes taxes & fees
Nov 5 - Nov 6
An unusual two-storey apartment with beams and an open fire.
A bedroom with a bed, a yellow sofa, and a skylight.

16. 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 CA $225
CA $255 total
includes taxes & fees
Oct 28 - Oct 29
Kick back and relax in this stylish apartment, 12 mins from Le Shuttle
A cozy bedroom with a wooden headboard, a bed with patterned pillows, bedside lamps, and a decorative sign on the wall.

17. 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)
"Beautiful property and absolutely lovely host."
United States
Alyson B.
The price is CA $216
CA $266 total
includes taxes & fees
Oct 26 - Oct 27
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
A rustic cabin with a wooden deck, a dining table, and a chair outside.

18. The Lookerer by Bloom Stays - a rural shepherds hut with amazing views!

The Lookerer by Bloom Stays - a rural shepherds hut with amazing views!
Ashford
10.0 out of 10, Exceptional, (51 reviews)
"The host was amazing. The hut was gorgeous and all little details were thought of which was so nice!"
United States
Anonymous traveller
The price is CA $374
CA $422 total
includes taxes & fees
Oct 27 - Oct 28
The Lookerer by Bloom Stays - a rural shepherds hut with amazing views!
A bedroom with a bed, bedside table, nightstand, and a ceiling light fixture.

19. Summerhill by Suspire

Summerhill by Suspire
3.0 star property
Ashford
The price is CA $265
CA $408 total
includes taxes & fees
Oct 26 - Oct 27
Summerhill by Suspire
A modern bedroom with a large bed, a sitting area with a chair, and a view of the garden through a glass door.

20. The Grain Store - a holiday let that sleeps 2 guests in 1 bedroom

The Grain Store - a holiday let that sleeps 2 guests in 1 bedroom
Rye
9.0 out of 10, Wonderful, (6 reviews)
"Beautiful accommodation, with lovely vaulted ceiling making it bright and airy High quality finishes all round Kitchen has everything you need and a bottle of milk waiting in the fridge was a lovely touch Tea bags, coffee pods, crisps and biscuits also provided Bed was comfortable and high quality bedding Lovely big fluffy towels and M&S toiletries provided. It was so quiet at night meaning a great night sleep A lovely stay and would recommend a trip to Caster sands and Rye center"
United States
Lynn B.
The price is CA $360
CA $360 total
includes taxes & fees
Oct 26 - Oct 27
The Grain Store - a holiday let that sleeps 2 guests in 1 bedroom
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

ORIDA Maidstone Hotel

ORIDA Maidstone Hotel

10/10 Excellent
"We had a lovely stay at the Orida Hotel in Maidstone! The hotel was clean, comfortable, and welcoming, with friendly staff who made the experience even better. The swimming pool was a real highlight and a great way to relax and unwind during our stay. The facilities were excellent, and the overall atmosphere was pleasant and relaxing. We really enjoyed our time here and would definitely recommend the hotel to anyone looking for a comfortable and enjoyable stay. We would happily return!"
Josh 3-night trip
Posted 13 hours ago
ORIDA Maidstone Hotel

Find out more about St Michaels

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in St Michaels?

Yes, we offer vacation rentals near popular points of interest in St Michaels, or you can choose a secluded option if you'd like a relaxing place to stay. Our travelers 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 vacation home rentals that St Michaels has to offer?

DADIO's Barn - Indoor Swimming Pool 400 Years Old & Hot tub: This vacation home rental near St Michaels is located on a lake and has an indoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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

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

What’s a vacation rental in St Michaels like?

A vacation rental is a private property you can book for a couple of days or more in St Michaels. Vacation rentals offer extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for families.