House holiday rentals in Tuckahoe

The Mint Cottage in Chesapeake City

The Mint Cottage is new to the air bnb market. It is a 3 bedroom Cape Cod on .5 acre lot in Charming Chesapeake City! The 1st floor features a master bedroom suite with updated amenities, large living room and kitchen, PLUS a full hair and makeup station (great for bridal parties). The 2nd floor has two bedrooms- a queen and 2 twin beds. The house features 3 full baths.The back yard has a private swimming pool, fire pit and patio. Terrific location to walk to waterfront, shops, and restaurants!

Strathmere Beachfront House

Luxury Beachfront Home Welcome to the Strathmere Beachfront home. A beautifully designed, luxury vacation home, where every detail is set to provide a you dream getaway. When you enter the home, you will be immediately taken by the panoramic ocean views from Atlantic City to Avalon. This well-appointed home, from chef’s kitchen Wolf and Sub-Zero appliances, to the Serena and Lily bedding, to the coastal / modern furniture, provides you and your family a welcoming environment. Treat yourself!

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

"The Townsend" - Hot Tub!

On the way to The Townsend, you'll pass roadside farmstands and open fields. This meticulously restored farmhouse, located on the Cohansey River, features waterfront views in every room in the house so you can unwind, reflect and enjoy the company of family and friends. Outside you'll find a fire pit, hot tub and large field, perfect for outdoor activities. A quick 3 mile drive takes you to the historic town of Greenwich. Please read "the space" section, which gives room-by-room detail.

Luxury Downtown Mansion! Garage Parking! Roofdeck!

Experience downtown Philadelphia in style while enjoying this luxurious and glamorous mansion! Beautiful open concept design with tons of natural light and comfy modern touches. BONUS 2 car parking! This spacious home has 5 Bedrooms/9 Beds/4.5 Bathrooms, gas fireplace, roof-deck with beautiful Philadelphia skyline views + plenty of outdoor seating! A+ Fairmount/Art Museum Location! Perfect home for family getaways, reunions, and groups looking to enjoy everything the city has to offer!

Red Point Lighthouse

Recently updated unique lighthouse replica on the northern tip of the Chesapeake Bay. 4 bedrooms & 2 sleeping nooks, the house can sleep up to 14 in 6 beds (3 kings, 1 queen, 2 doubles) and one queen sofa bed. 4 bathrooms - 2 ensuite. Two living rooms, fully equipped kitchen, family style dining area. Wrap around decks on multiple floors. Firepit, Adirondack seating, lawn games for enjoying 1.5 acres with water views. Community sandy beach across the street for strolling & relaxing.

Iconic Chesapeake. Unparalleled Luxury.

Summer at The Cottage at Silver Water is effortless and indulgent. A sweeping waterfront lawn leads to a private shoreline for swimming, kayaking, and long days in the sun. Evenings bring golden skies, spectacular sunsets, and fires by the water’s edge. Inside, the cottage is beautifully designed with luxurious bedding, curated art, and thoughtful amenities that make every stay relaxed, refined, and unforgettable. See why all our guests only have a 5-Star experience.

River front cottage with private dock & water fun

Private cottage on the banks of the Chester River. Sleeps 8-14. Private dock with plenty of water activities. This property offers relaxation and serenity as soon as you pull in! Located right on the water with spectacular views of the Chester River, the house is renovated in a cozy, casual farmhouse style. While you will love the house you will spend your days outside enjoying life on the river thanks to your private access to the water and lots of water fun!

Top of the Chesapeake - Private Waterfront Home

Our house is nestled between the shore of the NE River and the creek and marsh directly behind. The home is warm, unassuming and inviting; you'll feel right at home. Perfect for familes or groups, or a romantic weekend. Bird watchers will love the bald eagles, ospreys, kingfishers, mallards and cormorants, to name a few. The upstairs living room is a perfect place for the kids while the adults enjoy the lower area. You find our place warm, cozy and quiet.

Waterfront Farmhouse Retreat w/ Hot Tub & Fire Pit

Tucked along the banks of the Cohansey River, The Foxtail is a design-forward waterfront retreat set at the end of a long private lane. Recently refreshed throughout, the home blends its 1860s character with thoughtful modern updates, including a brand new kitchen, all new operable windows with screens, updated baths, and custom window treatments throughout. The result is a peaceful, comfortable river house that feels considered without feeling precious.

Waterfront Retreat w/ Hot Tub, Games & Views

Escape to River Haven, a 7,000+ sq. ft. waterfront retreat on the Susquehanna River, perfect for groups of up to 20. Relax in the hot tub, play pickleball, pool, ping-pong, and air hockey, or unwind on expansive decks with scenic views. The home features a fully equipped kitchen, spacious bedrooms, 4.5 baths, and family-friendly amenities. With a kayak launch nearby, trailer parking, and a whole-house generator, River Haven is made for memorable getaways.

The Garden Estate: Historic Town Center Home

Step back in time without sacrificing luxury. Nestled in Chestertown’s historic district, this rebuilt 19th-century estate blends grand character with modern comfort, just 4 blocks from Washington College. Sprawling across a rare town-center acre, the sanctuary features magnificent gardens, a fenced yard, a fire pit, and a Weber grill for evenings under the stars. Inside, find a flawless layout designed for privacy, rest, and premium comfort.