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Oceanfront Dock Escape ~ Kayaks & Paddleboards

House in Gloucester, MA

10 guests·4 bedrooms·3 bathrooms
5.0 · 40 reviews

Property details

This 4-bedroom house is in a prime location & has EVERYTHING you need for an amazing vacation to Gloucester, MA! • 13-minute drive to Wingaersheek Beach • 10-minute drive to Downtown Main Street in Gloucester • 2 inflatable Paddleboards • 4 Kayaks Available! • Outdoor Patio w/ Oceanfront Views • Large Jenga set • Fully Stocked Kitchen • Multiple Outdoor Spaces: Balcony/Deck • Family Friendly- Pack n Play & High Chair • Beach Essentials: Chairs, Umbrellas, Life Vests, Towels Quiet hours: 22:00 to 7:00. Pets: Not allowed. Smoking: Not allowed. Events: Not allowed. Suitable for: children and infants Nestled in the charming coastal town of Gloucester, our exquisite home offers the perfect year-round retreat with breathtaking panoramic water views. With 4 bedrooms and 3 bathrooms, our spacious sanctuary accommodates up to 12 guests, providing ample space for relaxation and adventure. Enjoy direct river and ocean access right from your own dock, where you can even catch striped bass right off the water! You can kayak or paddleboard right over to Wingearsheek Beach, making for a perfect day of exploration. The stunning bluestone patio offers an ideal spot for soaking up the sun. Conveniently located, our home is a gateway to explore the area's natural beauty, vibrant attractions, and delightful dining options. Experience the ultimate coastal getaway at our beautiful waterfront haven. MAIN SPACES OF THE HOME: – 4 BEDROOMS & 3 BATHROOMS – BEDROOM 1: * King-sized Bed * Twin-sized Trundle Bed * Smart TV * Ceiling Fan w/ Light * Wooden Drawer w/ Mirror * Nightstand and Lamps * End-of-the Bed Chairs * Ensuite Bathroom w/ Walk-in shower BEDROOM 2: * Full-sized Bed * Smart TV * Nightstand and Lamps * Ceiling Fan w/ Light * Plush Chair BEDROOM 3: * Full-sized Bed * Twin-sized Bed * Smart TV * Ceiling Fan w/ Light * Nightstand and Lamps BEDROOM 4: * Full-sized Sleeper Sofa * Smart TV * Plush Chair – 3 BATHROOMS – * Upper Level : 2 Full Bathrooms * Main Level: 1 Full Bathroom – CHEF’S KITCHEN – * Fully Stocked * High-end Stainless Appliances * Large Fridge * Nespresso Coffee Maker * Tons of Cabinetry & Large Island * Expansive Windows – LIVING ROOM– * 55" Smart TV * Large Plush Sofa & Chairs * Hanging Egg Chair * Open Floor Concept directing to the Kitchen & Dining Area * Expansive Windows –LOFT LIVING SPACE– * Smart TV * Plush Chair * Full-sized Sleeper Sofa The guest has access to the entire home minus the locked cleaners closet. Beyond the Property: Gloucester is a treasure trove of activities and experiences, perfect for travelers seeking both relaxation and adventure. From beachcombing and whale watching to indulging in local dining and shopping, there's something for everyone. Top Attractions: - Hammond Castle Museum: Explore medieval architecture, historical exhibits, and breathtaking ocean views. - Good Harbor Beach: White sandy shores, crystal-clear waters, and scenic low-tide walks. - Eastern Point Lighthouse: A photography hotspot with panoramic coastal views. - Stage Fort Park: Perfect for picnics, playgrounds, beaches, and a touch of local history. - Cape Ann Museum: Dive into the region's art and maritime heritage. - Maritime Gloucester: A charming waterfront museum featuring an aquarium and working harbor. Hidden Gems: - Dogtown Commons: Discover abandoned settlements with hiking trails and unique carved boulders. - Rocky Neck Art Colony: Wander through galleries and studios showcasing vibrant local art. - Ravenswood Park: Escape to peaceful trails ideal for hiking and birdwatching. Top Restaurants: - Azorean: Portuguese-inspired seafood dishes (133 Washington St). - Talise: Creative and locally sourced cuisine. - Tonno: A stylish spot for modern Italian seafood. - 1606 Restaurant & Oyster Bar: Waterfront dining with a refined menu. - Seaport Grille: Fresh seafood and harbor views (6 Rowe Sq). - The Franklin: Seasonal New American dishes in a cozy setting. - Lobstah Land: A casual eatery offering local seafood favorites. - Oak & Ember: Elevated dining with a steakhouse focus. Seasonal Highlights: - Whale Watching: Embark on unforgettable tours departing from the harbor. - Gloucester Schooner Festival: Experience schooner races and maritime celebrations every Labor Day weekend. - St. Peter's Fiesta: Celebrate Gloucester’s fishing heritage with lively parades and boat races. State Tax Number: C0484721070 Check-in is at 4pm Check-out is at 10am *NO PETS ALLOWED - No parties allowed—violations may result in immediate termination of the stay. We aim to maintain a respectful environment for our neighbors. - Parking in the driveway for 3 cars max. Street parking allowed: NO - Guests must be 21 years or older to book this property. GUEST VERIFICATION: To help ensure a smooth and secure stay for all guests, the primary guest listed on the reservation may be asked to complete a quick verification process within 48 hours of booking, depending on the platform used to book the reservation. Prior to check-in, guests may also be asked to sign a Rental Agreement that includes agreeing to our rental terms and conditions and, on certain booking platforms, providing a valid government-issued ID and matching credit card before arrival. Included with your booking is our damage waiver coverage, which helps protect against accidental, self-reported damage during your stay when reported prior to check-out. C0484721070 ROC-21038977-003

Sleeping arrangements

Bedroom 1

1 King Bed

1 Single Bed

Bedroom 2

1 Double Bed

Bedroom 3

1 Double Bed

1 Single Bed

Bedroom 4

1 Sofa Bed

Livingroom

1 Sofa Bed

What’s included

  • Self check-in

    Self check-in

  • Parking

    Parking

  • Washer

    Washer

  • Dryer

    Dryer

  • Heating

    Heating

  • Kitchen

    Kitchen

  • Wi-Fi

    Wi-Fi

  • Balcony

    Balcony

Guest reviews

Star icon 5.0 | 40 reviews
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J

Jennifer

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August 2026

Our family of 4 (Husband, wife, 19, and 16) had the BEST week at Kylie's beautiful Gloucester home. We took FULL advantage of the kayaks, back deck, view, fully-stocked kitchen, grill, and all the nooks and crannies to relax both inside and outside the home. Each of our daughters had friends come and go throughout the week....the house comfortably accommodated the extra guests. This is our 4th house that we've rented in the Gloucester/Rockport area and this one might be our favorite....we couldn't get over the views and loved to watch a specific crane and a specific cormorant (that seemed to love riding the strong tides of the Annisquam River. The one bit of feedback that I shared with the homeowner is that the house is on a blind curve. Although the speed limit is only 20 mph in each direction, folks seem to fly around the corner. You need to roll down your window and listen for cars. A helpful addition would be a mirror to see if cars are coming which Kylie appreciated.

A

Aamer

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August 2026

Great place and great host Thanks kylie

W

Wallace

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July 2026

Amazing location and house - we had an great time sitting on the deck overlooking the water.

R

Reid

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June 2026

Kylie’s home far exceeded my expectations. The location is perfect. Just minutes from town while still feeling private and secluded. The house was comfortable, spotless, and had everything we needed. I would highly recommend it for any group looking to stay in the area.

Know before you go

Self check-in

House rules

Check-in: 4:00pm

Checkout: 10:00am

No pets allowed

Min. age to rent: 21

No smoking

No parties

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