Holiday rentals in New Windsor
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in New Windsor
Guests agree: these stays are highly rated for location, cleanliness and more.
Flat in Sykesville
4.96 out of 5 average rating, 125 reviewsHickory Haven •1B King •Bsmt Apt •Clean •LG
Walk into a generously spacious, open-concept apt. The comfortable furnishings in this home blend authentic styles with modern design. Start your mornings w/ a meticulously clean bathroom. Enjoy movie night in the large living room, or lay on the comfortable king-sized bed. Read through the night by a warm stove fire. Stay in the backyard and enjoy the serenity of Sykesville! Enjoy the high-speed internet and the large space for your work-at-home needs. Stay-a-while and make the place your home.
25 Jun – 2 Jul
Cabin in Myersville
4.97 out of 5 average rating, 247 reviewsCabin 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.
19–26 Mar
Guest house in Westminster
4.86 out of 5 average rating, 271 reviewsThe Pig Shed Writer’s Retreat at Barter Lady Farm
Newly renovated with all new bathroom! The Pig Shed is an idyllic setting, close to Gettysburg and McDaniel College. Dogs under 50lbs welcome for Additional Fee, see House Manual for rules/fees for dogs. A unique retreat, fantastic for exploring local sites and nature watching. The studio features a queen sized bed, a full size futon, 3/4 bath, microwave, air fryer, hot plate, gas grill, incredible views and lots of quiet, access to a pond, hiking trails, a fire pit, and can visit the chickens.
9–16 Apr
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for New Windsor holiday rentals
Other great holiday rentals in New Windsor
Townhouse in Westminster
4.78 out of 5 average rating, 130 reviewsCozy Historic Westminster - Close to everything!!
29 Dec – 5 Jan
Farm stay in Union Bridge
4.93 out of 5 average rating, 176 reviewsUB Paradise - Rustic, Relaxing, Amazing View
2–9 Jun
Home in New Market
4.94 out of 5 average rating, 112 reviewsHistoric Peace and Plenty Farm: Pool House
21–28 Dec
Tiny home in Shippensburg
4.89 out of 5 average rating, 540 reviewsThe Eagles Nest
26 Mar – 2 Apr
Guest house in Fairfield
4.88 out of 5 average rating, 127 reviewsGettysburg-Ski-Golf-ATHikes - RoseSniffers Loft
8–15 Feb
Guest suite in Union Bridge
4.95 out of 5 average rating, 21 reviewsUB@Peace- Fully Separated 2 Bedroom Guest Suite
30 Aug – 6 Sep
Home in Keymar
4.92 out of 5 average rating, 24 reviewsKeymar Cottage
21–28 Apr
Home in Union Bridge
4.88 out of 5 average rating, 25 reviewsFarmhouse Getaway | Close to Wineries & Breweries
29 Jan – 5 Feb
Guest house in Frederick
5.0 out of 5 average rating, 75 reviewsA Quiet Haven
11–18 May
Guest suite in Mount Airy
4.96 out of 5 average rating, 54 reviewsPrivate in-law suite on farmette
9–16 Aug
Guest suite in Hampstead
4.92 out of 5 average rating, 64 reviewsSOLASE FARM RETREAT COZY COUNTRY SUITE
24 Nov – 1 Dec
Treehouse in Frederick
4.96 out of 5 average rating, 46 reviewsCharming Downtown Treehouse
20–27 Mar
Destinations to explore
- Baltimore Holiday rentals
- Arlington Holiday rentals
- Bear Holiday rentals
- Lancaster Holiday rentals
- Alexandria Holiday rentals
- Bethesda Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
- New York Holiday rentals
- Jersey City Holiday rentals
- The Hamptons Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom