35 Best Vacation Rentals in Picton - Holiday Lettings - Cabins

Close

View larger map

Also consider

Milford
10 properties

Picton

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

137 Vacation rentals

12

Picton Vacation guest house rental

Prince Edward County / Picton

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 15 mi
  • Child friendly
  • Air conditioning
Located in downtown Picton, this newly renovated, modern and exceptionally clean Carriage House offers private parking, outdoor dining area with Weber BBQ and 2 bedrooms that comfortably sleeps 4 people. Perfect for a friends weekend away or a couples retreat! Quiet and …see more

from $151 / night

$1,053 / week

Book View

Responds fast!
avg. 13 minutes

from $151 / night

37

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 $414 / night

$2,069 - $2,761 / week

Book View

Responds fast!
avg. 1 hour 21 minutes

from $414 / night

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 $188 / night

$1,132 - $1,358 / week

Book View

from $188 / night

(1) Excellent 

37

Vacation cottage in Picton

Prince Edward County / Picton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Turtle Crossing Cottage, a Country home on West Lake, Prince Edward County, is just minutes from Sandbanks Provincial Park. Open year-round our cottage is a perfect getaway for a couple or a group of up to six people. Minimum booking is 2 nights. Step back in time and …see more

from $211 / night

$1,430 - $1,655 / week

Book View

Responds fast!
avg. 1 hour 9 minutes

from $211 / night

11

Vacation home in Picton

Prince Edward County / Picton

5 13 3 nights min

  • 5 bedrooms
  • Sleeps 13
  • 3 nights min
  • 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 $301 / night

$1,587 / week

Book View

from $301 / 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 $1,129 / night

$7,898 / week

Book View

from $1,129 / night

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 $290 / night

$1,618 / week

Book View

from $290 / 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 $162 / night

$809 - $1,166 / week

Book View

from $162 / 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 $225 / night

$1,125 - $1,501 / week

Book View

from $225 / night

(3) Very Good 

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 $252 / night

$1,260 - $1,806 / week

Book View

from $252 / night

(5) 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 $264 / night

$1,843 / week

Book View

Responds fast!
avg. 1 hour 51 minutes

from $264 / night

(9) Excellent 

12

Vacation home with swimming pool in Picton

Prince Edward County / Picton

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 $76 / night

$376 - $1,204 / week

Book View

Responds fast!
avg. 1 hour 31 minutes

from $76 / night

(8) Excellent 

14

Vacation home in Picton

Prince Edward County / Picton

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 $82 / night

$226 - $1,580 / week

Book View

Responds fast!
avg. 1 hour 54 minutes

from $82 / night

(10) 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 $94 / night

$602 / week

Book View

Responds fast!
avg. 3 hours 32 minutes

from $94 / night

(35) Excellent 

Certificate of Excellence

39

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 $91 / night

$459 - $587 / week

Book View

Responds fast!
avg. 40 minutes

from $91 / night

52

Milford Vacation b&b rental

Picton / Milford

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning
  • Private garden
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 overlooking 2 acres towards the Black River shoreline. Come and experience …see more

from $128 / night

$895 / week

Book View

Responds fast!
avg. 42 minutes

from $128 / night

(1) Excellent 

52

Vacation b&b in Milford

Picton / Milford

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Air conditioning
  • Private garden
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 overlooking 2 acres towards the Black River shoreline. Come and experience …see more

from $129 / night

$898 / week

Book View

Responds fast!
avg. 42 minutes

from $129 / 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 $151 / night

$1,053 / week

Book View

Responds fast!
avg. 3 hours 14 minutes

from $151 / night

(5) 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 $188 / night

$1,129 - $1,354 / week

Book View

from $188 / night

(34) Excellent 

52

Milford Vacation b&b rental

Picton / Milford

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
  • Nearest beach 28 mi
  • Air conditioning
  • Private garden
ONLY ONE ROOM REMAINING FOR VICTORIA DAY WEEKEND (Minimum stay is 2 nights) 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 t …see more

from $128 / night

$895 / week

Book View

Responds fast!
avg. 42 minutes

from $128 / 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 $200 / night

$997 - $1,426 / week

Book View

from $200 / night

(11) Excellent 

Certificate of Excellence

38

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 $113 / night

$565 - $734 / week

Book View

Responds fast!
avg. 40 minutes

from $113 / 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 $113 / night

$800 - $1,064 / week

Book View

from $113 / night

17

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 $158 / night

$790 - $1,125 / week

Book View

from $158 / night

(1) Very Good 

16

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 $143 / night

$715 - $1,016 / week

Book View

from $143 / 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 $170 / night

$1,091 - $1,223 / week

Book View

Responds fast!
avg. 3 hours 14 minutes

from $170 / night

(6) Excellent 

57

Vacation villa in Picton

Prince Edward County / Picton

4 12 2 nights min

  • 4 bedrooms
  • Sleeps 12
  • 2 nights min
  • Nearest beach 32 mi
  • Ask about children
  • Air conditioning
Spoil yourself with a relaxing All Season Getaway in Prince Edward County. The Towers Manor Guest House is located in the heart of Prince Edward County. The home offers an executive and exclusive country getaway. You can't help but appreciate the newly renovated kitche …see more

from $376 / night

$2,628 / week

Book View

Responds fast!
avg. 3 hours 48 minutes

from $376 / 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 $658 / night

$4,603 / week

Book View

Responds fast!
avg. 1 hour 40 minutes

from $658 / night

(14) 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 $76 / night

$526 / week

Book View

Responds fast!
avg. 1 hour 53 minutes

from $76 / 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 $72 / night

$491 / week

Book View

Responds fast!
avg. 3 hours 32 minutes

from $72 / 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 five bedroom vacation retreat is located in a quiet rural area close to Milford, about 20 minutes from the Sandbanks beaches and less than 10 minutes to …see more

from $188 / night

$941 - $1,317 / week

Book View

from $188 / night

37

Milford Vacation home rental

Picton / Milford

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning
  • Private garden
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 overlooking 2 acres towards the Black River shoreline. Come and experience …see more

from $128 / night

$895 / week

Book View

Responds fast!
avg. 42 minutes

from $128 / 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 $151 / night

$978 / week

Book View

Responds fast!
avg. 3 hours 14 minutes

from $151 / night

56

Vacation cottage in Milford

Picton / Milford

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
SAFE, SHALLOW, SANDY BOTTOM, CRYSTAL CLEAR WARM WATER; SWIM, FISH, SNORKEL, KAYAK, CANOE, 50FT. DOCK, PLAY ON OUR 26' SAILBOAT ALL JUST DOWN A 100M WALKWAY. ENJOY THE CHARM OF A BEAUTIFUL AUTHENTIC KNOTTY PINE WELL EQUIPPED COTTAGE. Walk down the short, lush 100M path …see more

from $143 / night

$996 / week

Book View

from $143 / 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 $339 / night

$2,106 - $3,009 / week

Book View

from $339 / night