Family-friendly holiday rentals in Maryland

Cabin on Middle Creek - Myersville MD - Middletown

Park the car & walk across the creek on the foot bridge to serenity along Middle Creek. Nestled between South Mountain State Park & Gambrill State Park, lies a beautiful & relaxed 9-acre private cabin retreat. Great place to unwind & de-stress. Let the sound of the creek or rain on the tin porch roof put you to sleep at night. It has all the essentials of home. Enjoy the fire pit on cool evenings or take a dip in the stream on a warm day. The cabin offers a perfect peaceful or romantic setting

Sleepy Hollow Log Cabin

Sleepy Hollow Log Cabin at Beechnut Springs is nestled in the majestic Blue Ridge Mountains. A short distance from Rt 70 as you travel down scenic route 17 following a bustling trout stream to Beechnut Springs entrance. After you arrive & settle into your secluded cabin, you will find many unique activities & quiet places in this serene setting amid the wonders of quiet waterfalls, easy walking paths, a wildlife haven, natural running streams & "The Bog Shack". Welcome to Sleepy Hollow Log Cabin

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Bird's Eye View

Nestled high amidst the sturdy branches, "Bird's Eye View" is a sanctuary suspended between earth and sky. Located less than 5 minutes from Deep Creek Lake and perched among the foliage, our treehouse offers a panoramic perspective of the surrounding forest, granting its visitors an unparalleled vantage point to observe nature's wonders. Relax in the hot tub and take in an amazing sunset. The home is a harmonious blend of locally-crafted art and furniture to add rustic charm and modern comfort.

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

Treehouse in Deep Creek Lake

Newly built, Whispering Woods is a custom-made treehouse surrounded by stunning scenery just minutes from Deep Creek Lake and Wisp Resort. No detail was overlooked in the spacious interior that includes 2 bedrooms, 2 baths, a fully equipped kitchen, and a sitting area with a 65” TV. The amazing outdoor living space includes expansive decks, a fire pit, and a bubbling hot tub. For a unique and memorable experience from start to finish, come relax and reconnect at this treetop escape.

Long Beach Cottage, Hot Tub, Beachfront

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

Annapolis Garden Suite

Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a locked door; separate entrances).

Tiny A-Frame Retreat in the Woods

Beautiful, quiet woodland setting with a creek running through it, just 5 miles from downtown Frederick. Tucked away into the woods our tiny A-Frame has a comfortable queen bed(not an air mattress) for a rest and retreat fully immersed in the poplar woods. This is a camping style set up- so if you enjoy camping then this place is for you. No running water- but plenty of good clean mountain water available , no electricity, compost toilet. We do not allow dogs.

Rest and Recharge Retreat

We have a new larger tent for 2026! Queen size bed. We have also added a sauna to our retreat. Rest and recharge at this beautifully landscaped glamping retreat. Enjoy quiet moments of zen in the meditation garden, awake to the birds and butterflies, float the afternoon away in the pool or enjoy stargazing in the hot tub at night. We are set up for a quiet retreat for 2 people. Additional guests must be approved in advance. No parties!

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”).