35 Best Vacation Rentals in Picton - Holiday Lettings - Cabins

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126 Vacation rentals

(1) Excellent 

19

Picton Vacation apartment rental

Prince Edward County / Picton

3 9 2 nights min

  • 3 bedrooms
  • sleeps 9
  • 2 nights min
  • Nearest beach 14 mi
  • Child friendly
  • Air conditioning
A beautiful century home, located in downtown Picton. Your apartment is the entire top floor above Purtelleigh’s Bakery & Suites. Your entrance is located beside the driveway and you are greeted by a foyer and grand staircase. The upstairs has a parlour with a wall of w …see more

from $255 / night

$1,553 / week

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from $255 / night

(1) Excellent 

45

Vacation home in Picton

Prince Edward County / Picton

5 18 min stay varies

  • 5 bedrooms
  • sleeps 18
  • min stay varies
  • Nearest beach 16 mi
  • Child friendly
  • Air conditioning
This is the perfect house and surroundings for a large group, whether it's family gatherings or a friend’s retreat. Welcome to the renovated Three Little Birds Farmhouse nestled on 58 acres of private woodlands. 20 minutes by car to Sandbanks Provincial Park (2 par …see more

from $475 / night

$2,374 - $3,168 / week

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Responds fast!
avg. 1 hour 14 minutes

from $475 / night

11

Vacation home in Picton

Prince Edward County / Picton

5 13 min stay varies

  • 5 bedrooms
  • sleeps 13
  • min stay varies
  • Child friendly
  • Air conditioning
Barley Days Stays is a Rentable Farm House Located in the Heart of Prince Edward County. It is a cozy 5 Bedroom house big enough for the whole family. 10km From Sandbanks Provincial Park 2Km from Picton, On 2Km from Bloomfield, On Right beside Barley Days Brewery Incl …see more

from $226 / night

$1,584 / week

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Responds fast!
avg. 16 minutes

from $226 / night

(1) Excellent 

18

Vacation home rental

Prince Edward County / Picton

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 23 mi
A great place for visiting business and VIP executives, international travellers, couples, girls weekend getaways, cycling enthusiasts (we have sheltered and secure bike storage) . Upscale, welcoming and centrally located, 6 Edgecliffe is a 3 bedroom home (2 king beds …see more

from $238 / night

$1,856 / week

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from $238 / night

(1) Excellent 

12

Cottage rental in Picton

Prince Edward County / Picton

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 20 mi
  • Air conditioning
Perched on the edge of the escarpment, you have a spectacular view of the Glenora Ferry as it shuttles between Prince Edward County and Adolphustown. With the high rainfall this year, you also have a beautiful view of your very own waterfall. This is truely a very spe …see more

from $1,294 / night

$9,058 / week

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from $1,294 / night

22

Vacation home rental

Prince Edward County / Picton

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Air conditioning
  • Pet friendly
Stay in a charming two bedroom apartment with a balcony overlooking the bay, right next to the historic White Chapel. Located right between Parson's Brewery and the Golf Course at the north end of the town of Picton. You can easily stroll to the course to enjoy a game a …see more

from $195 / night

$1,209 / week

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from $195 / night

5

Picton Vacation home rental

Prince Edward County / Picton

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
Escape to the County! This home is a circa 1883-year-old gracious lady. Located on a quiet street alongside lovely homes. Take a short stroll to the main street of Picton and the pretty sailing harbour. Vibrant restaurants with lively pubs alongside artisans and art gal …see more

from $367 / night

$2,568 / week

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from $367 / night

14

Home rental in Milford

Picton / Milford

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Pet friendly
Relax and unwind in the modern comfort of this private getaway. Perched high above scenic South Bay, you will enjoy the tranquility and the view offered by this two bedroom waterfront cottage. It's a natural paradise and home to a variety of birds and wildlife too. Walk …see more

from $186 / night

$928 - $1,338 / week

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from $186 / night

(10) Excellent 

12

Vacation home with swimming pool in Picton

Prince Edward County / Picton

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
Private,quiet location 5 minutes from the sandbanks,great area for swimming,biking,hiking...you will find it peaceful .open concept guesthouse sleeps 4 comfortably..note 2 queen beds.lots of trees for shade,full sun around salt water pool.very pet friendly..microwave,co …see more

from $130 / night

$691 - $1,381 / week

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avg. 1 hour 24 minutes

from $130 / night

(7) Excellent 

32

Vacation home in Picton

Prince Edward County / Picton

5 9 min stay varies

  • 5 bedrooms
  • sleeps 9
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 14 mi
  • Child friendly
The White Rabbit Guest House is a charming and newly renovated Ontario cottage style century home located in the heart of Prince Edward County in the town of Picton. Situated on Main Street, it is within easy walking distance to cafes, restaurants, galleries, shops, the …see more

from $259 / night

$1,813 / week

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Responds fast!
avg. 1 hour 45 minutes

from $259 / night

(39) Excellent 

Certificate of Excellence

50

Vacation home in Milford

Picton / Milford

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 47 mi
  • Air conditioning
COME EXPERIENCE RIVER LIFE!! Ask for our off-season special. Stay a third night free with two nights booked with stays between Nov. 1 -April 30. Our hot tub is open year round! YOU ARE VIEWING THE ISLAND MILL GETAWAY'S COUNTRY SUITE , a lovely, large suite on the seco …see more

Certificate of Excellence

from $104 / night

$527 - $674 / week

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Responds fast!
avg. 17 minutes

from $104 / night

(14) Excellent 

Certificate of Excellence

42

Vacation watermill in Milford

Picton / Milford

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 58 mi
  • Air conditioning
EXPERIENCE RIVER LIFE! Ask for OUR SPECIAL 3RD NIGHT FREE with 2 nights booked with stays from Nov 1 - Apr 30. Our hot tub is open year round! We have two rental suites, THE MILLER'S RETREAT, a truly unique getaway with a private entrance, full kitchen and a riverside …see more

Certificate of Excellence

from $130 / night

$648 - $842 / week

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Responds fast!
avg. 17 minutes

from $130 / night

(3) Very Good 

24

Vacation home in Picton

Prince Edward County / Picton

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 10 mi
  • Child friendly
  • Air conditioning
Welcome to The Carrington...in the heart of PEC! This beautiful turn of the century home has been renovated to include all the modern comforts while still maintaing its original charm. Located in the heart of the county, we are moments away from beautiful wineries, Well …see more

from $195 / night

$1,360 / week

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Responds fast!
avg. 14 minutes

from $195 / night

31

Vacation home in Picton

Prince Edward County / Picton

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
Authentic mid-century modern bungalow overlooking Picton Bay and located on three acres of park-like setting on the outskirts of town. With four bedrooms, three bathrooms, a spacious living room and a billiards room, it’s a great location for family gatherings and get-t …see more

from $258 / night

$1,291 - $1,722 / week

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from $258 / night

(37) Excellent 

52

Milford Vacation b&b rental

Picton / Milford

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Nearest beach 28 mi
  • Air conditioning
  • Private garden
Please contact us for date and bedroom availability - thank you! Quiet, peaceful and pastoral describe this rural bed and breakfast conveniently located in the heart of Prince Edward County near Waupoos and the Black River Cheese Company. We have a new hot tub overlook …see more

from $190 / night

$1,329 / week

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Responds fast!
avg. 55 minutes

from $190 / night

(4) Excellent 

21

Vacation home in Picton

Prince Edward County / Picton

3 9 min stay varies

  • 3 bedrooms
  • sleeps 9
  • min stay varies
  • Child friendly
  • Air conditioning
Overlooking the Picton Harbour in the heart of Prince Edward County, this 3 bedroom vacation home is a perfect blend of modern convenience with historic charm. Tour the County wineries, visit the Sandbanks Provincial Park beaches, sample the regional cuisine and peruse …see more

from $290 / night

$1,446 - $2,072 / week

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from $290 / night

35

Picton Vacation home rental

Prince Edward County / Picton

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
PLEASE NOTE: When contacting for booking please include your home town, age range of guests, purpose of rental & some information about you and your guests. Guests may not bring any visitors or any others to our home at any time, for any length of time. Only those indi …see more

from $216 / night

$1,510 / week

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from $216 / night

20

Milford Vacation home accommodation

Picton / Milford

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Pet friendly
Experience cottage life in Prince Edward County! Listen to the loon calls early in the morning and watch the sun rise over South Bay while enjoying the comfort of the new gazebo. Relax on the deck and enjoy the breath-taking view while sipping on your morning coffee. Dr …see more

from $189 / night

$945 - $1,377 / week

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from $189 / night

(10) Very Good 

14

Vacation home in Picton

Prince Edward County / Picton

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 28 mi
  • Child friendly
  • Air conditioning
Hidden Treasure is our cozy, 4 season, vacation rental on Treasure Cove Lane, in Prince Edward County designed in the 80s with cottage-family-living in mind. Our cottage is ideal for casual and respectful cyclists and travelers alike. AC, WiFi, ceiling fans and 2 small, …see more

from $130 / night

$604 - $1,898 / week

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Responds fast!
avg. 2 hours 56 minutes

from $130 / night

(1) Excellent 

22

Vacation home in Picton

Prince Edward County / Picton

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
  • Air conditioning
Chapel Street Guest House (c. 1890) is located in the heart of Picton and an easy stroll to downtown. Located halfway between Toronto and Ottawa, it's a wonderful spot for family get-togethers & vacations, meetings & retreats away from the office, or a home base for you …see more

from $236 / night

$1,178 - $1,705 / week

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from $236 / night

15

Picton Vacation apartment rental

Prince Edward County / Picton

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
Loyalist Lofts are now in our ninth year of providing clean comfortable suite rentals. We offer three delightful suites to choose from. Each beautifully maintained apartment is equipped with modern efficient conveniences in a relaxing comfortable environment. Loyalist L …see more

from $173 / night

$1,209 / week

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Responds fast!
avg. 3 hours 15 minutes

from $173 / night

(1) Very Good 

14

Vacation home rental

Prince Edward County / Picton

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning
Ultra chic, ultra hip, ultra new two bedroom vacation suite located on Lake Street in Picton. 15 minute drive to the beach ~ 15 minute walk to downtown Picton for shopping, restaurants, cafes, live entertainment, and the historic Regent Theatre. This newly renovated su …see more

from $155 / night

$773 - $1,118 / week

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from $155 / night

(5) Very Good 

7

Picton Vacation studio rental

Prince Edward County / Picton

Studio 4 2 nights min

  • Studio
  • sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 16 mi
  • Child friendly
We are located within a short walk of the very quaint downtown core of Picton, Ontario. We are minutes from the beaches of the Sandbanks Provincial Park. Come see the picturesque Prince Edward County by way of a wine tour. Lake on the Mountain is always worth a visit …see more

from $83 / night

$563 / week

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from $83 / night

(7) Very Good 

12

Picton Vacation cottage rental

Prince Edward County / Picton

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
The cottage is right on the water and just a short walk from the outdoor heated pool, playground, basketball/tennis courts and sandy beach. The entire family can enjoy complimentary canoe, kayak and paddleboat/boards as will as a variety of Kidz Club activities. The ful …see more

from $173 / night

$1,554 / week

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from $173 / night

(21) Excellent 

10

Apartment rental in Picton

Prince Edward County / Picton

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Child friendly
Loyalist Lofts are now in our ninth year of providing clean comfortable suite rentals. We offer three delightful suites to choose from. Each beautifully maintained apartment is equipped with modern efficient conveniences in a relaxing comfortable environment. Loyalist L …see more

from $194 / night

$1,251 - $1,402 / week

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Responds fast!
avg. 3 hours 15 minutes

from $194 / night

15

Picton Vacation apartment rental

Prince Edward County / Picton

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Air conditioning
  • Private garden
On The Ridge is a spacious open concept apartment with the best of two worlds. Located in a tranquil country atmosphere however, within 5 minutes to downtown Picton with all its amenities (LCBO, Metro, Sobeys, No Frills, Rexall, Giant Tiger, Regent Theater, banks, ho …see more

from $129 / night

$915 - $1,066 / week

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Responds fast!
avg. 33 minutes

from $129 / night

16

Vacation apartment in Picton

Prince Edward County / Picton

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Air conditioning
  • Private garden
New, adults only, private self-catered/self-contained suite situated on lower level of ranch-style bungalow in park-like setting overlooking beautiful Picton Bay. Central to wineries, Sandbanks Provincial Park, Lake on the Mountain, 2 km to Picton, 1 km to Golf Course. …see more

from $194 / night

$1,208 - $1,359 / week

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from $194 / night

(13) Very Good 

Certificate of Excellence

8

Vacation condo in Picton

Prince Edward County / Picton

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 13 mi
  • Child friendly
Unit Two has a large living space and a spacious bedroom. There is an open concept livingroom, kitchen and diningroom with an executive bathroom. The executive bathroom is a 3 piece boasting a large beautiful tile/glass shower. This unit sleeps up to 6 people, with the …see more

Certificate of Excellence

from $108 / night

$691 / week

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from $108 / night

23

Vacation home in Picton

Prince Edward County / Picton

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
Cobalt Cottage is located in the heart of Prince Edward County where it blends in among the heritage street-scape of Picton. Located halfway between Toronto and Ottawa, it's a wonderful spot for get-togethers & vacations, and a home base for your Prince Edward County ad …see more

from $182 / night

$907 - $1,295 / week

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from $182 / night

28

Milford Vacation home rental

Picton / Milford

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Milford Meadows is perfect for gatherings of family and friends with lots of space both indoors and out. This private four bedroom + family suite vacation retreat is located in a quiet rural area close to Milford, about 20 minutes from the Sandbanks beaches and less tha …see more

from $224 / night

$1,118 - $1,597 / week

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from $224 / night

(17) Excellent 

Certificate of Excellence

31

Picton Vacation apartment rental

Prince Edward County / Picton

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
We would love you to stay in our vacation apartment 'Lazy Dayz' which is part of our home with it's own separate entrance and patio. The apartment is on one floor with no stairs which makes it easily accessible, and you can park free right outside your door. Take break …see more

Certificate of Excellence

from $87 / night

$605 / week

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Responds fast!
avg. 1 hour 45 minutes

from $87 / night

25

Picton Vacation home rental

Prince Edward County / Picton

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
Welcome to a one-of-a-kind deluxe family-friendly cottage located in beautiful Prince Edward County. This renovated dog friendly cottage is on scenic West Lake facing west to catch the beautiful sunsets. It’s minutes drive away from the beaches of Sandbanks Provincial …see more

from $826 / night

$5,783 / week

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from $826 / night

19

Picton Vacation home rental

Prince Edward County / Picton

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Private garden
Architects own house on Adolphus Reach in Prince Edward County. The Reach Guesthouse offers a spectacular experience in a retrofitted 1890's farmhouse that has been sculpted into a sustainable modern work of art. Large and bright, this house features an exceptional eat …see more

from $203 / night

$1,420 / week

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from $203 / night

11

Apartment rental in Picton

Prince Edward County / Picton

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
Loyalist Lofts are now in our ninth year of providing clean comfortable suite rentals. We offer three delightful suites to choose from. Each beautifully maintained apartment is equipped with modern efficient conveniences in a relaxing comfortable environment. Loyalist L …see more

from $173 / night

$1,122 / week

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Responds fast!
avg. 3 hours 15 minutes

from $173 / night

12

Vacation home in Picton

Prince Edward County / Picton

5 12 4 nights min

  • 5 bedrooms
  • sleeps 12
  • 4 nights min
  • Child friendly
The Sunny Lane House showcases a new gourmet open floor plan kitchen and gorgeous master ensuite. You are located a mere 300 steps to historic downtown Picton for shopping, antiquing and dining. You are at the perfect home base for exploring the county. A 15 minute …see more

from $389 / night

$2,416 / week

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from $389 / night

Great rentals within 20 miles that match your search

Distance approx 15.68 miles from Picton Show on Map

(1) Excellent 

11

Vacation apartment in Ameliasburgh

Prince Edward County / Ameliasburgh

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 23 mi
  • Private garden
Begin your tour of Prince Edward County at Meraki County Suites. The word "meraki" means "to do something with soul, creativity, or love", and that is how we've created our guest suite. Open year-round. Located in the peaceful countryside of Ameliasburgh, you can watch …see more

from $95 / night

$665 / week

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from $95 / night

Distance approx 7.09 miles from Picton Show on Map

(9) Excellent 

10

Vacation b&b in Prince Edward

Prince Edward County / Prince Edward

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 10 mi
  • Air conditioning
Fields & Forest Sweet suite - a relaxed adult environment Your "hygge" home base - Cosmopolitan comforts / country space & setting 4 acres Mid-century style in the middle of "The County" Easy elegance in a modern environment Private entrance & personal patio Lofty bed / …see more

from $125 / night

$876 / week

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from $125 / night

Distance approx 4.84 miles from Picton Show on Map

(6) Excellent 

19

Bloomfield Vacation cottage rental

Prince Edward County / Bloomfield

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Child friendly
Nestled on Bloomfield's Main Street, the Doctors house Bloomfield is in beautiful Prince Edward County. This home has been called The Doctors House by most of it's old time residents as it was the home of Dr. Cahoon and his family for over 56 years. This historic 4 bedr …see more

from $302 / night

$2,071 / week

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Responds fast!
avg. 47 minutes

from $302 / night

Distance approx 18.95 miles from Picton

43

Carrying Place Vacation home rental

Prince Edward County / Carrying Place

3 10 3 nights min

  • 3 bedrooms
  • sleeps 10
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
AUG 26-31 STILL AVAILABLE Free WIFI and NO ADDITIONAL CLEANING FEES. The house is a beautiful 3 bedroom, 1 bathroom with open concept kitchen, dining and living room. The kitchen dining area opens onto a large deck with BBQ and patio tables and chairs that overlook a …see more

from $216 / night

$1,467 / week

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from $216 / night

Distance approx 8.97 miles from Picton Show on Map

21

Napanee Vacation cottage rental

Lennox and Addington County / Napanee

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Ask about pets
This cottage sits at the waters edge with a panoramic view from the living room, family room and spacious upper deck. Wake up to an amazing view of the water and have your morning coffee on the sheltered deck off the master bedroom. In the evenings, enjoy a glass of the …see more

from $324 / night

$1,941 - $3,623 / week

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Responds fast!
avg. 3 hours 29 minutes

from $324 / night

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