Monthly Rentals in Sherwood

Discover long-term rentals that feel like home for stays of a month or longer.

Nearby monthly rentals

Superhost
Cottage in Wittman
4.87 out of 5 average rating, 151 reviews

Perfect St. Michaels Getaway

SamRating, 5 stars1 month ago
This cottage was a gorgeous place to relax with my wife for her birthday. The proximity to the bay cannot be beat - especially since she made kayaks available for our stay. I would happily re-book next time I am in the area.
Guest favourite
Home in Saint Michaels
4.95 out of 5 average rating, 56 reviews

Private&Cozy/3br+2ba/1mi to town

CarrieRating, 5 stars3 days ago
Fantastic spot!! Close to St.Michael’s and restaurants, etc. The house was in a peaceful, quiet location right outside of town. Had all the amenities you could need. We would definitely return!! Thank you
Top guest favourite
Home in Tilghman Island
5 out of 5 average rating, 18 reviews

Panoramic water views

MeganRating, 5 stars1 month ago
This was one of the loveliest Air BnBs I’ve had the pleasure of staying at. The photos don’t do it justice. A warm, welcoming and cozy home, filled with sunlight and stunning water views from every window. You literally feel like you’re on a boat! Comfortable furnishings and beds, a super well-stocked kitchen with lovely dishes and decor, bikes, kayaks, gas grill… everything you could want. The Tilghman Island General Store was just a short walk through a lovely neighborhood with the friendliest people. Breakfast at Two if by Sea was amazing! And crab cakes at Gina’s on the Bridge were delish. My dog loved the stay too! Tilghman Island is a peaceful treasure in today’s crazy world.
Guest favourite
Cottage in Wittman
4.89 out of 5 average rating, 165 reviews

"Wittman Cottage"

JamesRating, 5 stars3 weeks ago
Wonderful location. Excellent accommodations. Been there a few times and each visit has been most pleasant.

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term holiday rentals and a single monthly payment without additional charges.*

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Work-friendly spaces for digital nomads

Travelling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing and relocation needs.
*Some exclusions may apply in certain geographies and for some properties.
  1. Airbnb
  2. United States
  3. Maryland
  4. Talbot County
  5. Sherwood
  6. Monthly Rentals