Holiday rentals in New Windsor

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Top-rated holiday rentals in New Windsor

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Cabin in Myersville

4.97 out of 5 average rating, 247 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.

13–20 Mar

$153 SGD per night
Guest favourite

Flat in Sykesville

4.96 out of 5 average rating, 125 reviews

Hickory 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.

26 Jun – 3 Jul

$119 SGD per night
Guest favourite

Guest house in Westminster

4.86 out of 5 average rating, 271 reviews

The 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

$138 SGD per night

Popular amenities for New Windsor holiday rentals

Other great holiday rentals in New Windsor

Superhost

Townhouse in Westminster

4.78 out of 5 average rating, 130 reviews

Cozy Historic Westminster - Close to everything!!

17–24 Jan

$265 SGD per night
Superhost

Serviced apartment in Westminster

4.88 out of 5 average rating, 106 reviews

Lovely 2-bedroom apartment near McDaniel College

24–31 Dec

$261 SGD per night
Guest favourite

Home in New Market

4.94 out of 5 average rating, 112 reviews

Historic Peace and Plenty Farm: Pool House

13–20 Feb

$349 SGD per night
Guest favourite

Farm stay in Union Bridge

4.93 out of 5 average rating, 176 reviews

UB Paradise - Rustic, Relaxing, Amazing View

3–10 Jun

$250 SGD per night
Guest favourite

Guest house in Fairfield

4.88 out of 5 average rating, 127 reviews

Gettysburg-Ski-Golf-ATHikes - RoseSniffers Loft

14–21 Feb

$113 SGD per night
Guest favourite

Guest suite in Union Bridge

4.95 out of 5 average rating, 21 reviews

UB@Peace- Fully Separated 2 Bedroom Guest Suite

31 Aug – 7 Sep

$171 SGD per night
Guest favourite

Home in Keymar

4.92 out of 5 average rating, 24 reviews

Keymar Cottage

1–8 Jun

$132 SGD per night
Guest favourite

Home in Union Bridge

4.88 out of 5 average rating, 26 reviews

Farmhouse Getaway | Close to Wineries & Breweries

29 Jan – 5 Feb

$177 SGD per night
Guest favourite

Guest house in Frederick

5.0 out of 5 average rating, 75 reviews

A Quiet Haven

11–18 Dec

$154 SGD per night
Guest favourite

Guest suite in Mount Airy

4.96 out of 5 average rating, 54 reviews

Private in-law suite on farmette

9–16 Aug

$188 SGD per night
Guest favourite

Guest suite in Hampstead

4.92 out of 5 average rating, 64 reviews

SOLASE FARM RETREAT COZY COUNTRY SUITE

12–19 Oct

$130 SGD per night
Guest favourite

Treehouse in Frederick

4.96 out of 5 average rating, 46 reviews

Charming Downtown Treehouse

9–16 Nov

$148 SGD per night

Destinations to explore

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