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Chatham Vacation Rental home in Cape Cod MA, Pleasant Bay, Jack Knife Beach: 1/2 mile | ID 36274
5 BR
4 ½ baths
Sleeps 10
Beds: 1 king, 3 queens, 2 twins
Beach: Pleasant Bay, Jack Knife Beach: 1/2 mile
OWNER SPECIAL: Book Now and Experience Chatham's Best Family Vacation in 2026!
Daily
Weekly
Monthly
Off-season 2025/26
$428 - $1,571
Summer 2026
 
Off-season 2026/27
$428 - $1,571
Off-season 2025/26
$3,400 - $11,400
Summer 2026
$14,400 - $16,400
Off-season 2026/27
$3,400 - $11,400
Off-season 2025/26
$10,000 - $40,000
Summer 2026
$55,000
Off-season 2026/27
$10,000 - $20,000
Listed by JC & Kristin
Active
3+ years
Property ID 36274
9
Description

Description

"Truly a work of art" best describes "Sip of Sunshine", Chatham's newest family vacation destination.

Thoughtful design and quality craftsmanship are clearly evident in this 5 bedroom, 4.5 bath home set on over an acre of land and walking distance to Jack Knife Beach on Pleasant Bay, Ryder's Cove and Crow's Pond. A complete restoration project a few years ago, along with the addition of a 2 car garage with private suite above, resulted in this fun-filled home brimming with character and charm. Perfectly suitable for relaxed living both inside and out, this beautiful home will not disappoint. Central air conditioning, a beautiful eat-in chef's kitchen with cathedral ceiling, living room with gas fireplace, first floor primary suite, three season screened porch, half bath, and mud room comprise the first floor.

The second floor of the main house includes 2 bedrooms and a "Jack & Jill" bathroom. The east wing has an attached 2 car garage with a spectacular suite above serving a variety of purposes to customize the home as needed. Decks on both the first and second floors overlook a fabulous gunite in-ground heated saltwater pool, surrounded by artistic stonework and professionally designed landscaping. <br /> <br /> SOS's latest upgrade (2022) is an additional new suite with a Queen sized bed, lounge, big screen TV, and beautiful new full sized bathroom.<br /> <br /> Sip of Sunshine is "Cape Comfortable" with well-appointed decor from Serena and Lily, Mitchell Gold, Room & Board, Ralph Lauren, William Sonoma, Restoration Hardware and many local artists.<br /> <br /> Our home is perfect for families with lots of private outdoor space for swimming, bird watching, grilling, bocce, spike ball, corn hole and a fire pit for the kids to roast s'mores. From the back decks you can glimpse the fishing boats on Ryder Cove. Indoors you will find board games, cards, and a beach library. The garage provides a full gym for your vacation fitness with Concept 2 bike and rower, barbells, weights, kettlebells, and medicine balls. The house is wired with Sonos, and each TV has a Roku so you can access your favorite home streaming channels. <br /> <br /> Take a sunrise walk to Crows Pond or Ryder's Cove, watch the sunset over Pleasant Bay and family friendly Jackknife Beach, or grab a bike and hit the Cape Cod Rail Trail. Your Cape adventures are everywhere.<br /> <br /> Looking for a night out on the town, "Sip of Sunshine" is just a few miles from downtown Chatham, Wequassett and Chatham Bars Inn. Check out our guest welcome book for Cape Cod dining and activity suggestions.<br /> <br /> Generac Home Generator ensures that your vacation will not be interrupted if a storm hits.<br /> <br /> We invite you to our home to enjoy the best of Cape Cod.<br /> <br /> Important Information<br /> * There is a $400 cleaning fee.<br /> * $1000 security deposit (refundable).<br /> * Local & MA taxes (14.45%) apply.<br /> * Cancellation policy (please see owner's rental agreement).<br /> <br /> read more show less

Location

Location - Chatham

Nearest beach: Pleasant Bay, Jack Knife Beach: 1/2 mile

41.7117369 -69.9840535 0
Photos

Photos

Pricing & Availability

Pricing & Availability

1
OWNER SPECIAL:
Book Now and Experience Chatham's Best Family Vacation in 2026!
Minimum Stay Requirements:
  • Off-season 2025/26
    2 nights
  • Summer 2026
    7 nights
  • Off-season 2026/27
    2 nights
Available
Unavailable
Unknown

Calendar Last Updated: January 06, 2026

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  • Price JANUARY 2026
      Sa
    Su
    M
    Tu
    W
    Th
    F
                  1 2
        3 4 5 6 7 8 9
     $3,400  10 11 12 13 14 15 16
     $3,400  17 18 19 20 21 22 23
     $3,400  24 25 26 27 28 29 30
     $3,400  31            
    Monthly: $10,000
  • Price FEBRUARY 2026
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $3,400    1 2 3 4 5 6
     $3,400  7 8 9 10 11 12 13
     $3,400  14 15 16 17 18 19 20
     $3,400  21 22 23 24 25 26 27
     $3,400  28            
    Monthly: $10,000
  • Price MARCH 2026
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $3,400    1 2 3 4 5 6
     $3,400  7 8 9 10 11 12 13
     $3,400  14 15 16 17 18 19 20
     $3,400  21 22 23 24 25 26 27
     $3,400  28 29 30 31      
    Monthly: $10,000
  • Price APRIL 2026
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $3,400          1 2 3
     $3,400  4 5 6 7 8 9 10
     $3,400  11 12 13 14 15 16 17
     $3,400  18 19 20 21 22 23 24
     $3,400  25 26 27 28 29 30  
    Monthly: $10,000
  • Price MAY 2026
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $3,400              1
     $5,400  2 3 4 5 6 7 8
     $5,400  9 10 11 12 13 14 15
     $5,400  16 17 18 19 20 21 22
     $7,400  23 24 25 26 27 28 29
     $11,400  30 31          
    Monthly: $18,000
  • Price JUNE 2026
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $11,400      1 2 3 4 5
     $11,400  6 7 8 9 10 11 12
     $11,400  13 14 15 16 17 18 19
     $11,400  20 21 22 23 24 25 26
     $14,400  27 28 29 30      
    Monthly: $40,000
  • Price JULY 2026
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $14,400          1 2 3
     $16,400  4 5 6 7 8 9 10
     $14,400  11 12 13 14 15 16 17
     $14,400  18 19 20 21 22 23 24
     $14,400  25 26 27 28 29 30 31
    Monthly: $55,000
  • Price AUGUST 2026
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $14,400  1 2 3 4 5 6 7
     $14,400  8 9 10 11 12 13 14
     $14,400  15 16 17 18 19 20 21
     $14,400  22 23 24 25 26 27 28
     $14,400  29 30 31        
    Monthly: $55,000
  • Price SEPTEMBER 2026
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $14,400        1 2 3 4
     $10,400  5 6 7 8 9 10 11
     $9,400  12 13 14 15 16 17 18
     $9,400  19 20 21 22 23 24 25
     $9,400  26 27 28 29 30    
  • Price OCTOBER 2026
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $9,400            1 2
     $8,400  3 4 5 6 7 8 9
     $8,400  10 11 12 13 14 15 16
     $8,400  17 18 19 20 21 22 23
     $8,400  24 25 26 27 28 29 30
     $8,400  31            
  • Price NOVEMBER 2026
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $8,400    1 2 3 4 5 6
     $5,400  7 8 9 10 11 12 13
     $5,400  14 15 16 17 18 19 20
     $7,400  21 22 23 24 25 26 27
     $5,400  28 29 30        
  • Price DECEMBER 2026
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $5,400        1 2 3 4
     $5,400  5 6 7 8 9 10 11
     $5,400  12 13 14 15 16 17 18
     $7,400  19 20 21 22 23 24 25
     $7,400  26 27 28 29 30 31  
    Monthly: $20,000
  • Price JANUARY 2027
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $7,400              1
     $3,400  2 3 4 5 6 7 8
     $3,400  9 10 11 12 13 14 15
     $3,400  16 17 18 19 20 21 22
     $3,400  23 24 25 26 27 28 29
     $3,400  30 31          
    Monthly: $10,000
  • Price FEBRUARY 2027
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $3,400      1 2 3 4 5
     $3,400  6 7 8 9 10 11 12
     $3,400  13 14 15 16 17 18 19
     $3,400  20 21 22 23 24 25 26
     $3,400  27 28          
  • Price MARCH 2027
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $3,400      1 2 3 4 5
     $3,400  6 7 8 9 10 11 12
     $3,400  13 14 15 16 17 18 19
     $3,400  20 21 22 23 24 25 26
     $3,400  27 28 29 30 31    
  • Price APRIL 2027
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $3,400            1 2
     $3,400  3 4 5 6 7 8 9
     $3,400  10 11 12 13 14 15 16
     $3,400  17 18 19 20 21 22 23
     $3,400  24 25 26 27 28 29 30
  • Price MAY 2027
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $5,400  1 2 3 4 5 6 7
     $5,400  8 9 10 11 12 13 14
     $5,400  15 16 17 18 19 20 21
     $7,400  22 23 24 25 26 27 28
     $9,400  29 30 31        
  • Price JUNE 2027
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $9,400        1 2 3 4
     $11,400  5 6 7 8 9 10 11
     $11,400  12 13 14 15 16 17 18
     $11,400  19 20 21 22 23 24 25
        26 27 28 29 30    
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Additional availability info: Contact Homeowner for Special Occasions, Long Term Stay and Annual Rebookings. This is a Saturday to Saturday vacation rental.

Payment Methods: Personal checks

Fee Breakdown:

INCLUDED IN WEEKLY RATE

Cleaning Fee:

$400

ADDITIONAL PRICING INFO

State and local taxes of 14.45% will apply

Amenities

Amenities

  • View of salt water View of salt water

  • Walk to a salt water beach Walk to a salt water beach

  • Central air Central air

  • Outdoor shower Outdoor shower

  • Washer&dryer Washer&dryer

  • Swimming pool Swimming pool

  • No Pets No Pets

  • Internet Internet

  • Linens provided Linens provided

  • Bathtub Bathtub

  • Firepit Firepit

  • Screened porch Screened porch



    Green Amenities

    9
    • Heat Pumps Heat Pumps

    • LED lighting LED lighting

    • ENERGY STAR appliances ENERGY STAR appliances

    • Adult bicycles Adult bicycles

    • Filtered water Filtered water

    • Eco-friendly cleaning supplies Eco-friendly cleaning supplies

    • Recycling Recycling

    • Reusable grocery totes Reusable grocery totes

    • Organic or Chemical-free lawns Organic or Chemical-free lawns

    About our green amenities: Fresh Herb Garden. Fruit and Vegetable Garden.

    Fresh Filtered Water in Kitchen.

    Well water for yard and garden.

    Bird feeder with lots of feathered friends.

    Reviews

    Guest Reviews

    20 reviews
    Have you stayed here? Write a review
    M S
    MA
    (Homeowner Entered)

    Great home. Great location. Great host.

    Date of stay: May 2024
    C S
    NY
    (Homeowner Entered)

    Had a wonderful February weekend at Sip of Sunshine with our group of 7 friends. We loved that the home had enough privacy for everyone, as well as great common space for us to gather together. We enjoy Chatham shopping/restaurants and the house was super convenient to easily access our favorite spots.

    Date of stay: February 2024
    K S
    CT
    (Homeowner Entered)

    Thank you for letting us stay at your beautiful home. Absolutely fantastic trip!

    Will definitely be back.

    Date of stay: October 2023
    K C
    VA
    (Homeowner Entered)

    Sip of Sunshine was the perfect home for our family! We loved the house and the location - everything was so beautifully decorated and we love the history of the home.

    Date of stay: October 2023
    K P
    MA
    (Homeowner Entered)

    Sip of Sunshine was the perfect location for our girls trip! The house was very spacious and had everything we needed. All of the bedrooms were clean and comfortable as well. JC was very helpful when it came to the house and recommendations for things to do in the area. Overall it was a great weekend away!

    Date of stay: September 2023
    D G
    NY
    (Homeowner Entered)

    Beautiful home with all the amenities including gorgeous in ground pool. Great location an added plus!

    Date of stay: September 2023
    J W
    NJ
    (Homeowner Entered)

    We had a wonderful time in your home! It was a relaxing week on the Cape. The space worked out very well.

    Thanks for the hospitality.

    Date of stay: July 2023
    S L
    IL
    (Homeowner Entered)

    Beautiful house - plenty of bedrooms and living space. Enjoyed the pool and outdoor area with friends. Great location for getting to restaurants and bars, and easy accessibility to the beach.

    Date of stay: June 2023
    B M
    CT
    (Homeowner Entered)

    Sip of Sunshine was the perfect home for our family getaway. It was just what we were looking for. JC greeted us and took the time to walk me through the home so we would have a hassle-free time. The home is not only spacious but also was very well appointed to handle a small celebration dinner. JC was not only accommodating but also very responsive to all inquiries. We could not have ask for anything better!

    Date of stay: June 2023
    L D
    MA
    (Homeowner Entered)

    My friends and I stayed at Sip of Sunshine for a girl's getaway trip to escape our crazy mom lives back home. It was the perfect home to unwind, relax and enjoy all of the fun things the cape has to offer. The home was clean, well equipped with everything we may need, and the outdoor pool area was perfect for entertaining and relaxing. The location was central to all of the cool restaurants and bars we visited, and it was extremely easy to get an Uber if we wanted to do so. The Sonos sound system throughout the house was a great addition - as well as the cool garage gym we used for working out. The owner was extremely helpful and available for all of our questions and very willing to help with making plans. We can't wait to re-rent this home next summer if available! show more show less

    Date of stay: June 2023
    About

    About JC & Kristin

    Member since:
    6/12/2022
    Reviews:
    20 reviews
    Response Time:
    Within a day
    What is special about your town?
    Rich in its maritime heritage, as well as a spirited New England town with a variety of small businesses, Chatham is a special place.

    You will find the natural beauty of Chatham remarkable. Visitors are drawn to the expansive and magnificent beaches, the lighthouse, wildlife, nature trails, bike path, and stunning views of the ocean. Chatham has a special blend of the past and present with quaint streets lined with historic sea captains' homes, a fine selection of historic museums, and a walking downtown area with unique shops, galleries, and restaurants.

    We hope you will find our town as special as we do, and that you will return many times in the future to enjoy the beauty of this wonderful seaside village and all that it has to offer.

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