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.
Top guest favorite
Home in Tilghman Island
5 out of 5 average rating, 18 reviews

Panoramic water views

MeganRating, 5 stars4 weeks 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 favorite
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.
Guest favorite
Home in Sherwood
5 out of 5 average rating, 11 reviews

Punch Point boasts a sandy beach w/ pool and pier

ErickaRating, 5 stars1 week ago
Marissa’s place is always amazing. As usual, the house was very clean and equipped with everything a family with kids would need. We cooked multiple meals and had everything we needed in the fully stocked kitchen. The extra refrigerator upstairs came in handy for leftovers. The playroom and garage were packed with toys and games for kids of all ages. Marissa has truly thought of everything. Downtown St. Michael’s is only a short drive away and well worth the visit. We look forward to returning again soon!

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 vacation rentals and a single monthly payment without additional charges.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

Work-friendly spaces for digital nomads

Traveling 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