Holiday rentals in Middletown

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Top-rated holiday rentals in Middletown

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Guest favourite

Cabin in Middletown

4.91 out of 5 average rating, 357 reviews

Charming vintage cabin in the ❤️ of Middletown.

Cozy cabin in the ❤️ of Middletown, MD. Within walking distance to quaint Middletown restaurants, shops, & parks. Set your sights on adventure within a short drive. Enjoy downtown Frederick restaurants, shops, parks, & nightlife. Visit the local wineries, breweries & festivals. Hike the Appalachian trail. Float the Potomac River. Bike the C&O Canal. Ski the slopes @ area ski resorts. Golf 18 holes @ the championship golf course. Visit wedding venues. Go antiquing. Tour quaint nearby towns. Etc

20–27 Dec

$205 SGD per night

Guest favourite

Cabin in Myersville

4.97 out of 5 average rating, 251 reviews

Cabin on Middle Creek - Myersville MD - Middletown

Park the car & walk across 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. Amazing place to unwind, de-stress & get away. 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.

10–17 Jan

$154 SGD per night

Guest favourite

Guest house in Middletown

4.95 out of 5 average rating, 245 reviews

Indulge, Fresh Flowers, Frederick County Haven

2 bedroom, full kitchen and laundry, 1 level guesthouse beside detached garage (separate from main house). The front has a rose garden, birdbath and your own patio. An apple tree is beside the guesthouse. A farm is to the back. Asian cafe, Subway, Dempsey's Grill, Amvets, Main Cup bar and restaurant, Tapia's and 3 ice cream parlors are all a short walk away. More restaurants and grocery store are less than a mile. Farmer's market in season on Thursdays. Fresh flowers and coffee are provided.

11–18 Aug

$144 SGD per night

Guest favourite

Guest suite in Myersville

4.93 out of 5 average rating, 278 reviews

Harmony Lodge nestled in wooded tranquility!

Tranquil lodge nestled on 3 wooded acres in Myersville, MD. Relax by the heated pool, enjoy the warmth of the fire pit, or walk the grounds and enjoy Mother nature. Minutes away from downtown Frederick and Middletown restaurants, shops, and parks. Visit the local wineries and festivals. Tour historic battlefields. Go antiquing. Take in a round of golf, bike the C&O canal, hike the Appalachian trail, boat on the Potomac River, or go skiing. Bring your fur baby with you to enjoy the activities!

12–19 Jan

$260 SGD per night

Guest favourite

Loft in Walkersville

5.0 out of 5 average rating, 128 reviews

Daysville Inn- Boho Farmhouse Apt

This farmhouse apartment is perfect for your next visit to the Walkersville/Frederick MD area! Peacefully private from the hosts’ home, and conveniently located just 2 miles from the popular Walkers Overlook Wedding Venue, and 7 miles from the fun downtown Frederick! With many popular breweries/wineries surrounding it, it’s your perfect weekend getaway! It even comes with 4 friendly goats our guests are welcome to pet! No hotels are closer! We hope you book your stay today at Daysville Inn!

23–30 Jul

$139 SGD per night

Guest favourite

Flat in Thurmont

4.9 out of 5 average rating, 163 reviews

Ted n Cindy's

This small, comfortable 235 sq ft efficiency apartment is Located on beautiful Mountaindale road just 3 miles back roads to Springfield Manor Winery and wedding venue Also located 1/2 mile below the Frederick Watershed With ride out and walk out to some of the best mountain biking, rock climbing and hiking in Maryland. A nice out outside covered fire pit with plenty of wood and tranquil creek across the street. Next door to Seven Gables Lodge Airbnb if you are part of a bigger group

23 Feb – 2 Mar

$156 SGD per night

Guest favourite

Guest suite in Smithsburg

4.99 out of 5 average rating, 151 reviews

Creekside Retreat at the Jewel Vinsota

Relax in a quiet, curated, dog-friendly art exhibit. Live with paintings & sculptures that are for sale. This garden apartment is tucked into a hillside above a creek, along the Jewel Vinsota Sculpture Trail. Your host/gallery curators live upstairs. The “Artist’s Guesthouse” is next door. The private entrance is down a stone-stepped path. Perfect for 2 w/ the queen bed but room for 4 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

21–28 Dec

$118 SGD per night

Guest favourite

Farm stay in Middletown

4.9 out of 5 average rating, 308 reviews

Fox Haven Organic Farm's Spring House

Peaceful countryside surrounds you with woods, streams, and pasture. The restored farmhouse has loads of room and porches where you can soak in a sunrise and a sunset. Birders paradise! Harper's Ferry, Frederick, Shepherdstown offer loads of fun and history. Two other houses, and a re-purposed Dairy Parlor are available for retreats too. Your stay supports farm programs that we offer children and adults from low income communities, people suffering with PTSD, and other life challenges.

16–23 Sep

$263 SGD per night

Guest favourite

Home in Myersville

4.97 out of 5 average rating, 145 reviews

The Crooked Cottage: a Cozy, Curated Escape

You will instantly relax in this stylish, pet-friendly home only 8 mins from I-70, exit 42. Under a canopy of trees find a beautifully landscaped yard with decks and two fire pit areas. Enjoy the well-apportioned kitchen with organic, fair trade coffee. Relax with 2 Roku TVs, games and puzzles, bathe with soaking salts and Turkish towels. For outdoor enthusiasts, pitch your tents. Sit by the wood-stove in the winter, or lay in a hammock when it’s warm. Welcome to The Crooked Cottage!

22–29 Jul

$228 SGD per night

Guest favourite

Guest house in Myersville

4.93 out of 5 average rating, 189 reviews

Spruce Run Cottage, Farm stay on Catoctin Mountain

The cottage is located on 25 acres of mostly wooded terrain off Highway 17 near Wolfsville, Maryland, less than an hour and a half from D.C. The cottage faces the woods and the private drive down to the creek. There is almost zero light pollution at night so stargazing is incredible from the balcony. The hosts live on the property up the hill in an 1890’s chink log cabin. Although you can see our house, the cottage feels very private and is a quiet comfortable retreat in the hills.

17–24 Jun

$136 SGD per night

Guest favourite

Guest house in Keedysville

4.98 out of 5 average rating, 190 reviews

City Dog Farm

Comfortable, light-filled one bedroom apartment on 10 acres in Maryland near Antietam battlefield and Harpers Ferry, WV. We have chickens, an organic garden, hills, woods and a stream. Apartment is 15 minutes from Harpers Ferry, Antietam battlefield, the C&O canal, river rafting on the Potomac or Shenandoah, vineyards, the Appalachian trail and small towns including Boonsboro and Shepherdstown, WV. 30 minutes to Frederick or Hagerstown/1.5 hours to DC or Baltimore. SORRY NO PETS

11–18 Jun

$171 SGD per night

Guest favourite

Apartment in Frederick

4.91 out of 5 average rating, 197 reviews

Your Hideaway awaits/1-bedroom downtown pad.

There is no place like home when you visit our cozy 1 bed/1 bath abode! This 2nd floor unit is nestled in the rear of a historic home that has been converted into condo living. This space checks all the boxes for a weekend getaway or long-term stay. Enjoy an open living/dinning area, a new memory foam king bed, & a fully furnished bathroom! We offer a keyless entry & 1 parking spot - a rarity for downtown living. Residents live above & below. NO pets, loud music, or parties.

23–30 Jul

$148 SGD per night