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ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms

Photo gallery for ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms

19 foot heated swim spa-4 ft deep for lap swimming, therapy seats, night lights
Living area
Living area
Living area
Living area

Reviews

10 out of 10
Exceptional
4 bedrooms3+ bathroomsSleeps 82700 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View in a map
St Michaels, MD
  • Place, Perry Cabin Park
    ‪17 min walk‬
  • Place, St. Michaels Marina
    ‪3 min drive‬
  • Place, Chesapeake Bay Maritime Museum
    ‪3 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪22 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 3- Shutters open to overlook living room and its skylight views to water

1 Queen Bed

Blue

2 Double Beds

Master Suite 2nd floor

1 Queen Bed

MBR-1st floor

1 King Bed

3 bathrooms, 1 half bathroom

!st floor Master Bath

Soap · Towels provided · Bidet · Toilet · Shower only · Jetted bathtub · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet · Shower only · Hair dryer

Bathroom 3

Soap · Towels provided · Bathtub or shower · Toilet · Hair dryer

Powder Room

Soap · Towels provided · Toilet

Spaces

Deck or patio
Kitchen
Office
Outdoor play area
Garden
Dining area

About this property

ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms

YOUR CHESAPEAKE DREAM GETAWAY-SPECIAL NIGHTLY RATE OF $950 FOR BOOKINGS MAY 26-30,JULY 16-19 and JULY 27-8/2
Fantastically Located: Just 1 mile from historic St. Michaels, offering the perfect blend of seclusion and convenience.
Unique Transportation Options:
• Harbor Shuttle available from private dock, avail for Sunset Cruises too
• Easy walk, run, or bike to town (only 1.1 miles)
• Close to Chesapeake Bay Maritime Museum
• Nearby ice cream shops, restaurants, and local attractions
Property Highlights
Outdoor Oasis
• Private, heavily wooded location on a secluded lane
• Expansive deck overlooking Long Haul Creek
• 19 foot temperature-controlled swim spa 5 feet deep
• 2-speed current for swimming
• Jetted seats
• Multi-colored lights
• Fountain spouts
Waterfront Amenities
• Private deep-water dock (30 & 50 amp power, water)
• Face-dock with 6’+ depth
• Boat-friendly slip
• Crabbing paradise (Crab pots provided!)
• Waterside firepit with complimentary wood
• Magnificent sunset views
• Views of Miles River Yacht Club
Recreational Equipment (All Included!)
• 5 Kayaks with life jackets
• 4 Bikes
• Outdoor pergola with dining table (seats 8)
• Weber barbecue
Interior Comfort
Living Spaces
• Natural light throughout
• Coastal-style interior
• Water views from almost every room
• Comfortable living room with expansive seating
• Game and TV areas
Gourmet Kitchen
• Open-plan design
• Double features:
• 2 sinks
• 2 dishwashers
• Double oven
• Cooking options: Gas and induction
• Fully equipped with:
• Blender
• Juicer
• Kitchen Aid mixer
• Coffee grinder
• Keurig machine
• Extensive spice collection
Bedrooms
First Floor Master Suite
• King-size 4-poster bed (new mattress)
• Direct deck access
• Gas fireplace (winter months)
• Wall-mounted TV
• Marble bathroom with:
• His and her vanities
• Bidet
• Glass shower
• Jetted soaking tub
Second Floor Master Suite
• Queen-size bed
• Water views
• Smart TV
• Connected skylit office/art studio
• French doors
Additional Bedrooms
• Third bedroom: Queen-size, peach-colored
• Fourth bedroom: Two double beds, blue-colored
• Newly renovated connecting bathroom
Extras
• Quality linens and towels provided
• Large swim spa towels
• Life vests available
• Pet-friendly (pending breed/size approval)
• No cats allowed
House Philosophy
This isn’t just a rental—it’s a beloved home carefully shared to help others experience the amazing Chesapeake Bay lifestyle. Guests are asked to treat the property with the same respect they would their own home.
Booking Details
• 7-night minimum stay in July and August preferred
• Flexibility considered when scheduling permits
• Additional reviews available on VRBO
Our prices include all fees. No hidden fees.

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House Rules

Check in after 5:00 PM
Minimum age to rent: 30
Check out before 10:00 AM
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Children

Children allowed: ages 3–17
Nice furnishings so well behaved kids only
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Events

No events allowed
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Pets

Pets allowed: dogs less than 23 kg per pet (limit one pet total)
Dogs will be considered on a case by case basis.
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Smoking

Smoking allowed: in designated areas
Checkout is 10 AM, $50 per hour charge for late checkouts due to cleaning schedule, unless otherwise agreed to by Agent.
$5000 damage protection insurance is required at a cost of $99.

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
Property Registration Number STRN-24-11

Frequently asked questions

Does ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

How much does it cost to stay at ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms?

As of 2 Apr 2026, prices found for a 1-night stay for 2 adults at ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms on 3 Nov 2025 start from £899, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

How much is parking at ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms?

On-site parking is available at the property.

What time is check-in at ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms?

Check-in begins at 5:00 PM.

What time is check-out at ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms?

Checkout is at 10:00 AM.

Where is ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms located?

Situated on the waterfront, this holiday home is within 2 miles (3 km) of Perry Cabin Park, Saint Michaels Town Hall and Muskrat Park. Higgins Yacht Yard and Marina and Chesapeake Bay Maritime Museum are also within 2 miles (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 33 out of 34 reviews
Rating 8 - Good. 1 out of 34 reviews
Rating 6 - Okay. 0 out of 34 reviews
Rating 4 - Poor. 0 out of 34 reviews
Rating 2 - Terrible. 0 out of 34 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Richard O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house and surrounding property was amazing. The best "home away from home" we have ever stayed at.
Stayed 7 nights in Aug 2025
Response from VrboOwner on 22 Aug 2025
Thank you for the nice review. I'm glad you had a great in my home!
Verified

10/10 Excellent

Daniel H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property at a wonderful location. We had a blast.
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Kathy M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We thoroughly enjoyed our stay. The house was very well equipped and comfortable. We took advantage of the bicycles, kayaks, fire pit and crab pots. A sunset cruise with pick-up at the property’s dock was a highlight.
Stayed 4 nights in Aug 2025
Verified

10/10 Excellent

Marlies C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Summer getaway

Lovely home in a lovely setting. Convenient to attractions. Really terrific!
Stayed 8 nights in Jul 2023
Response from VrboOwner on 4 Dec 2023
Thanks Marlies. Hope to have you back again. I rated you 5 stars on communication-but VRBO has listed it as 4 stars. I can't change it. So sorry- you were great to communicate wtih.
Verified

10/10 Excellent

Jennifer N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Just fabulous! Everything as advertised. The house is beautiful and comfortable. We loved eating outside on the covered patio and enjoyed time hanging out in the spa after walking around town. Crab traps at the dock are large and we caught a dozen blue claws! Great getaway!!!
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

LESLIE C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful and Idyllic

The home and grounds were lovely and we enjoyed our stay very much. Every detail was thought through, organized and easy. Our favorite moments were simply reading on the deck with our dog overlooking the Bay and being surrounded by the shade of all of the lush tall trees. Thank you so much.
Stayed 3 nights in Jul 2025
Response from VrboOwner on 11 Jul 2025
I'm so happy you had a relaxing time. Thank you for the lovely review and leaving the house in good shape.. I'm glad you enjoyed all the trees- actually as a game I had my grandson count them recently when he was visiting and there are over 140 on property! I hope you come back next summer!
Verified

10/10 Excellent

Amy V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for our family

We loved it here! It was in a private & beautiful location. The house was very comfortable and charming. We enjoyed the dock, fire pit and lap pool. Loved exploring on the bikes that were provided. Kath was a great host. Would definitely stay here again.
Stayed 7 nights in Jul 2023
Response from VrboOwner on 27 Jul 2023
So glad you had a great time. You were great guests. I’d love to see you again next year!
Verified

8/10 Good

Scott S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great time in a beautiful home

Great house in a beautiful setting. You’ll need to drive to downtown- unless you bike- but we had no trouble finding parking on Memorial Day weekend.
Stayed 3 nights in May 2023
Response from VrboOwner on 31 May 2023
I’m really disappointed you were the first guest to give me a 4 star rating out of 38 guest stays over the last 3 years rating it 5 stars. I was clear in my description it is 1.5 miles to town, which usually appeals to guests wanting some exercise, so sorry if you were disappointed and chose to drive. I am close enough so you can arrange for the Harbor Water Taxi to pick you up from my dock and the C-Street van will take you home later in the evening if you’ve had a few! And as you found out, parking isn’t a problem. But happy you thought my house was beautiful and in a great setting.
Verified

10/10 Excellent

Kelly R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Breathe and Light

Deep breath in the beauty, nature, pampering and stillness. Breath out your worries, tension, otherness. Let your natural light shine forth.
Stayed 3 nights in May 2024
Response from VrboOwner on 29 May 2024
It sounds like you really enjoyed the nature, privacy and calming effect of the water. I'm so happy that you were able to recharge and refresh here. Thank you for being such lovely guests. Please do come back!
Verified

10/10 Excellent

Elizabeth B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house on Long Haul Creek

Our group included two grandparents, two parents and two children, 9 & 11. The children were in sailing camp during the weekdays, but came home and really enjoyed the swim spa, as did the other family members. Kayaking and biking were the other activities that kept us thoroughly entertained. There were three kayaks for use by guests and four bicycles. The house is extremely well equipped, comfortable and in a great location in St. Michaels. We had a very nice two-week stay.
Stayed 14 nights in Jul 2023
Verified

10/10 Excellent

Thomas B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Stay

Our time at Kathi's place was perfect for our family of 3 (with a toddler) and two sets of grandparents. The setting is magical - surrounded by old growth trees and set right on the water, we had spectacular sunsets through our stay. The house is so well appointed and spacious including en suite bathrooms to all bedrooms. The pool was a fantastic amenity to have because it was small enough for our toddler to swim in but big enough for adults as well and easy to securely cover when not in use. The wrap around deck is inviting for having meals al fresco and happy hours. The yard is spacious for running around but shaded due to the trees. And the dock access to the water was great, especially for fireworks watching. We can't thank Kathi enough for being so welcoming and sharing her beautiful home with us.
Stayed 4 nights in Jul 2024
Response from VrboOwner on 15 Jul 2024
Thank you for such a wonderful and detailed review. Your stay at my home is what makes me enjoy sharing it with others to experience it's beautiful and restorative environment. You were such lovely guests and are welcome back anytime.
Verified

10/10 Excellent

Linda H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing house

We had our first family vacation (3 generations) in three years due to the pandemic. We all fell in love with the property. We had all kinds of plans but ended up spending much of our time at the house. It was so relaxing; a huge beautiful deck, beautiful view of the water, a wonderful infinity pool and more. We went kayaking off the dock and caught huge crabs off the dock (and Kath supplied everything you'd need to have a crab fest). Kath recommended some great restaurants and the property manager was so helpful in getting us acclimated to everything the property had to offer. We hated having to leave and go home. A truly memorable experience.
Stayed 3 nights in Sep 2022
Response from VrboOwner on 27 Jan 2023
Hi Linda, I was just updating my listing for this summer and saw that I neve thanked you for this very nice review. Hope you and your family are doing well. Kath
Verified

10/10 Excellent

Ann S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

The perfect peaceful spot to relax with family

We kayaked, rode bikes and even caught a crab from the end of the dock. Kathleen’s home is lovely with a gourmet kitchen, super comfortable bedrooms, a huge deck and lap pool our kids enjoyed. The location is terrific - very close to town, but a quiet idyllic setting. We highly recommend it.
Stayed 4 nights in Aug 2022
Response from VrboOwner on 18 Jan 2023
I’m so happy you had a great time. Hope to see you again next year.
Verified

10/10 Excellent

Heather A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house on the water

The house was clean and lovely to stay in. The spa/pool was broken the first half of our stay but the owner worked diligently/everyday to try and get it working. When it worked, it was great to use! Very close to all the restaurants and shops.
Stayed 5 nights in Aug 2022
Response from VrboOwner on 18 Jan 2023
You were lovely guests and your dogs were very well behaved. Thank you for being so understanding about the swim spa. Although it was totally swimmable, it took some time to figure out how to remove an object that was stuck in swim jet plumbing. I hope to see you again.
Verified

10/10 Excellent

Daniel M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome in every way

The house is great and well equipped. We brought much more than we needed. Wonderfully relaxing and very well located close to St. Michaels. Kath is a delight! We look forward to going back.
Stayed 14 nights in Jun 2022
Response from VrboOwner on 18 Jan 2023
Daniel your were a wonderful guest. So glad you enjoyed your stay. Hope to see you next year!
Verified

10/10 Excellent

Suzanne P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Home in St. Michael's

We had a lovely time at this home for a multi-generational family vacation this past week. We brought along our sailboat, SUPs and kayaks and spent a lot of time on the water, and out of the back deck which is an amazing space at this property. The location could not be better - easy drive or bike ride or sail into the town of St. Michael's. Highly recommend this property!
Stayed 7 nights in Jun 2022
Response from VrboOwner on 18 Jan 2023
You and family were incredible guests - you left the house so immaculate. Please don’t wait until next year to come back!
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Serene Waterside Location in St. Michaels

This serene and peaceful property was perfect for my family of 4 adults with two well-behaved dogs. We love the spacious yet cozy, homey feeling and the comfy beds. The wrap around deck and covered dining area offered very versatile outdoor spaces and the perfect place for playing cards together at the end of the day.
Stayed 9 nights in Jun 2022
Response from VrboOwner on 18 Jan 2023
So glad you had a good time. I’ll be sending your apple charger back- do you want the crab cards too?
Verified

10/10 Excellent

Bobby G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

fantastic location, lovely home

we loved Kath's home.
Stayed 7 nights in May 2022
Response from VrboOwner on 18 Jan 2023
Glad you had a good time.
Verified

10/10 Excellent

Tracy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A perfect family gathering destination.

A beautiful, peaceful home, inside and out, that 3 generations enjoyed immensely - from sitting on the deck looking at the beautiful view to exploring in the kayaks. The host, Kath, and the property manager were extremely kind, helpful, and responsive. We highly recommend this lovely spot.
Stayed 3 nights in Sep 2021
Response from VrboOwner on 18 Jan 2023
I’m so glad you had great weather and a good time. Your Mother is adorable! Please do come back. Kath
Verified

10/10 Excellent

Jen N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Spot

The house was a perfect weekend getaway on a beautiful property. Thanks for everything!
Stayed 3 nights in Sep 2021
Response from VrboOwner on 18 Jan 2023
So glad you had a good time. You had beautiful weather for the wedding you attended!
Verified

10/10 Excellent

Laura P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Serene, beautiful house near town

Serene, beautiful house near town Great communication, expectation set. Lovely house in a peaceful setting, near the village of Saint Michael’s.
Stayed 3 nights in Sep 2021
Verified

10/10 Excellent

Sherri C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property!!

We had an awesome time! Location is great, property is beautiful and has every amenity needed to have a great time. Owner is great at communicating and property manager took us through the house and explained everything to us. Which light switches work which lights and how to use the TV! So important for renters!!
Stayed 4 nights in Sep 2021
Response from VrboOwner on 18 Jan 2023
I’m so glad you had a great time. Please do come back next Year! Kath
Verified

10/10 Excellent

Barb B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Waterfront serenity

We have been to St Michaels several times but it was our first visit to Southport. This home is waterfront serenity with your cup of coffee or evening glass of wine. Very lovely, home with comfortable beds, equipped kitchen, fire pit and crab traps. Hilights included kayaking, our homemade crab dip, cornhole competitions and the evening fire pit. Awesome weather allowed us to eat all of our meals, and enjoy cards on the large deck. Wish we could have stayed longer!
Stayed 4 nights in Sep 2021
Response from VrboOwner on 18 Jan 2023
Barb thank you for being such a wonderful and flexible guest. Please do come back.
Verified

10/10 Excellent

jackie w.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Labor Day getaway

The house was beautiful inside but the view of the water from the deck and the dock was even better. Great location and very close to downtown St Michaels. The owner and property manager did everything they could to make our stay perfect. We will definitely treasure the memories made here kayaking, fishing off the dock, enjoying the deck and swim spa, and enjoying a fire in the evenings. Would recommend to anyone looking for an escape less than 2 hrs from DC.
Stayed 4 nights in Sep 2021
Response from VrboOwner on 18 Jan 2023
I'm glad you enjoyed my home. But your violating the clearly stated 8 persons ( except under 2 yrs old) maximum of people on my property at any time when rented, resulting in my getting cited by Talbot County for this violation, will interfere with my getting my short term rental license renewed. And dealing with this violation at my renewal hearing in a County that regulates STR's so strigenty because they don't want them will be a huge problem for me. Fortunately I wasn't assesed the first violation $1000 fine and I chose not to make you leave the property immediately, as I could have. So anyone considering renting my home, be aware that Talbot County strictly enforces the maximum of 8 people on my property at any time. Not even drop in guests are allowed. In my first year of renting , everyone else has loved my home, treated it with care and adhered to the agreed upon terms. If you chose to rent it, you'll need to do the same and have an equally wonderful time.
Verified

10/10 Excellent

Jennifer L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect family vacation

This house was perfect. Such a beautiful setting and location. Sunrise kayaking and sunset boating was awesome. We all loved it.
Stayed 7 nights in Jul 2021
Response from VrboOwner on 18 Jan 2023
Glad you were able to Kayak a lot- sunrise kayaking is the best if you are an early riser!!!!Thanks for the nice review.

About the host

Hosted by Owner

Host profile image
I fell in love with St Michaels after I sailed here for the first time. I searched for a piece of land , designed and built the house in 1989. My career was in Philadelphia so this was a great place to relax and sail. I later met my future husband, but since we lived in different states for our first 9 years, this was where we spent our weekends. Plus, he was a Naval Architect so my deep water dock was a great place for our boat collection!

Why they chose this property

It's so relaxing, quiet and private. I love the all the trees and nature and the constantly changing scenery with the occasional boat going by, fish jumping, beautiful sunrises and moonrises. And the firepit at night brings back great memories me of my childhood camping in New Hampshire.
Be aware I don't use chemicals on my lawn because its bad for the Chesapeake Bay, so its not perfection but great for bare feet! Though I do have the property sprayed for ticks.

What makes this property unique

The favorite area of this property for most guests is the expansive private deck to relax on throughout the day and night, enjoying the solitude, the surrounding natural beauty, star gazing in the night sky, and watching occasional boats slowly glide by. Whether you want shade or sun, the deck offers both. The views of sunsets from the dock are magnificent, something to create memories.
The focal point of the deck is the expansive pergola and outdoor dining table that easily shelters and seats 8 people. But if you want to exercise after eating a meal you cooked on the outdoor barbeque, there is a 19-foot heated swim spa with a 2-speed current you can swim against on the deck. The spa can easily accommodate children playing water games and adults relaxing in jetted seats. If you want adventure, exploring, or exercise, guests can use any of the five kayaks with life jackets.
The interior of the house is special for so many reasons that cater to guest wishes. Natural light flows throughout the house, giving you the feeling you are outside in nature even when you are lounging comfortably inside the house. The house interior furnishings combine comfort and coastal style. This is not a sparsely furnished rental property. This is a stylish home that shows pride of ownership, inside and out, accented by original art, with comfortable seating and sleeping furnishings.
This property is in a secluded, heavily wooded location, but still just slightly over 1 mile from the heart of downtown Saint Michaels with its renowned shops, diverse restaurants and bars, and even 3 ice cream stores if you feel the need for a dessert before you work it off in the swim spa, on a bike, taking a walk, or paddling a kayak. The property is on a private lane, ideal for walks, exercising a dog, or using one of the 4 bikes that are available on the property.
This property and this home will offer you a unique combination of style, comfort, and nature that will create lifelong memories
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