Escape to Waterfront Tranquility at Sip Into Sunset

A Luxury Cottage w/ Private Dock and Hot Tub

On Gwynn's Island at the heart of the Chesapeake Bay

2 bedroom · 2 bath · Up to 6 Guests

We love talking with guests! Call or text at (804) 808-1080

Enjoy the most breathtaking sunsets from our private pier where the Rivah meets the Bay. Our charming cottage has everything you can think of and more for a waterfront escape.

How many beds?

  • 4 beds

Where is it?

  • Cherry Point Community on Gwynn's Island

What is nearby?

  • Community Beach & Boat Slip

  • Mathews Main Street

  • Chesapeake Wine Trail

  • Virginia River Realm

What are ALL the amenities?

  • Private Dock

  • Hot Tub

  • Fire Pit with Firewood

  • Gas BBQ Grill

  • Patio & Screen Porch

  • High Speed Wifi and Streaming TV

  • Beach Essentials

  • Pet Friendly Fenced Yard

  • Water Toys

The Space

The breathtaking views beckon the minute you arrive. It's impossible resist walking immediately to the dock and enjoying the 180 degree views of the water. The firepit lounge area, the hot tub, and the outdoor shower are just icing on the cake. We know you'll be dreaming about this space for years to come after you've made some amazing memories here.

Luxury Amenities

Our smart locks will be set with your personalized code for contactless check-in. You'll walk into the vaulted screen porch, then enter through the updated kitchen, complete with a coffee bar and a breakfast bar with seating. The spacious, vibey living room beckons with oversized couches, a SmartTV, and a fun bar cart. Adjacent is the dining room, with almost 180 degree water views and seating for 6. and a full kitchen with breakfast bar island seating to the right. The first bedroom offers a queen sized bed, SmartTV, and closet space, plus a decorative fireplace. Our second bedroom has a king bed, a SmartTV, and closet space.

Our two full baths, one with a tub/shower combo, are fully stocked with bath products and luxury towels. The outdoor shower is an experience not to be missed, and is also fully stocked with products.

Off the screen porch there is a game room with all the water toys you need to enjoy your stay, plus crab pots, nets, and fishing poles. We also have an air hockey table and a large screen TV with a video game console. The full sized washer and dryer are located here, along with an extra full sized refrigerator.

Outside is the true oasis, however. Never miss a sunset from our private dock, complete with swim ladder for easy water access. The fenced yard offers privacy without blocking the incredible water views, and makes for a pet friendly space. Our herb garden is yours to enjoy, whether for cooking or cocktails! We provide firewood for a cozy night around the firepit, with seating for 6. The string lights create ambiance over the hot tub, which is a must-experience, especially at sunset.

Enjoy our community amenities, including a pier where neighbors meet nightly for cocktails at sunset, a sandy beach with parking, and a boat slip.


3 off-street parking spaces

Sleep & Comfort

1 King Bed

1 Queen Bed

2 Full Pull Out Sofa Beds

Full Bathroom for Each Bedroom

Plus Outdoor Shower - Summer Months

Bath Products Provided

Pack & Play

Fun & Sport Equipment

Fire Pit and Lounge Furniture

Kayaks & SUP

Crab Pots & Fishing Poles

Adult Bikes

Board & Video Games for all ages

Beach Chairs & Floats

Beach Towels

Game Room

Floating Mat

Cooking & Dining 

Fully stocked Kitchen

Screen Porch with Dining & Lounge Areas

Dining room with Water Views on 3 sides

Gas BBQ Grill

All Kitchen Appliances Provided

French Press, Coffee Maker, & Keurig


We Welcome All Kinds of Families

Pet Friendly

Full Size Washer & Dryer

Special Pricing for Longer Stays


Community Beach



Tracy & Jen

Making Waves Hospitality


Welcome to Sip Into Sunset, a place near and dear to our hearts. Gwynn's Island is one of our favorite places on Earth, and this cottage was renovated with our love and care, and with our guests as our first priority.

Tracy fell in love with Gwynn's Island in 2019 when she and her partner purchased a vacation home on the island. They've hosted loved ones and friends for long weekends and beach parties for the last few years. That's how Jen was introduced to Gwynn's Island, and became a permanent fixture at their house. One night over wine and a beach fire, we decided to share this special place with the world and agreed to launch our hospitality company when the right property came up.

You see, Tracy is a top tier Realtor and property manager, and Jen is an interior designer. So we pooled our talents and when this beautiful location became available we snatched it up! So many hundreds of hours of planning, preparation, designing, purchasing, and renovation went into this property, and so much of our own blood, sweat and (occasional) tears.

That's why each item in the home is special to us, and every decision was made remembering what we loved (and didn't!) from our own girls' weekends and family vacations. As one guest recently put it, "This place was obviously conceived and provisioned by people with the gift of hospitality."

We hope you love this place as much as we do - nothing gives us more joy than hearing from our guests and the memories they've made while at The Sip.


Jen & Tracy

Making Waves Hospitality


This place was great for our family vacation! Great space, clean, and perfectly decorated. Short walk to the beach, and you can’t beat the private pool! The kitchen included everything we needed for cooking meals. Our hosts were very quick to respond with any questions we had during our stay. Highly recommended!

-Savannah and Elijah

This place was Amazing! We loved it! Location was perfect. Matt was quick to respond to any of my messages. The 2 separate houses are perfect for large groups so you can be together but also have privacy as well. We will be staying here again for sure.