Monthly Rentals in Sherwood

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

Nearby monthly rentals

Top guest favourite
Flat in Chester
4.97 out of 5 average rating, 262 reviews

Cozy Waterfront Apartment Chester, MD

BrettRating, 5 stars4 months ago
We needed a quiet and private space to relax. Jordan’s space was all of this. We stayed here for a month and hardly ever heard Jordan and her family. Jordan was quick to respond if we had any questions. The bed was very comfortable and the views of the water were nice.
Top guest favourite
Cottage in Saint Michaels
4.98 out of 5 average rating, 230 reviews

The Little Anchor Cottage, St. Michaels, MD

JulieRating, 5 stars2 weeks ago
Excellent stay!! Charming cottage home, a block from the water/ park and a block from the main street. Quiet, peaceful. Irmina and Alain were quick to respond to any questions and checked on us. Top notch stocked kitchen, snacks, drinks. Clean with ample space. This was the perfect location for our trip. We will 100% be back and chose this home. Thank you again!
Superhost
Cottage in Wittman
4.87 out of 5 average rating, 150 reviews

Perfect St. Michaels Getaway

LaurenRating, 5 stars3 weeks ago
We had a very peaceful stay! The surrounding area was very nice. The queen bed was soooo comfortable!! Only thing to be mindful of is the stairs, they can be a little tricky without a railing on one side. But the host was very communicative and quick to respond when we had questions and we really enjoyed our stay!
Guest favourite
Cottage in Wittman
4.89 out of 5 average rating, 160 reviews

"Wittman Cottage"

SusanRating, 5 stars3 weeks ago
This is a very special place. From the moment we pulled into the driveway, we were enchanted by the beautiful location. Water views everywhere, birds singing, bunnies hopping across the lawn - a peaceful, lovely place. The house is very comfortable. There were just two of us but it could easily be shared with another couple or as a family. The screened porch was a great setting for outdoor dining and sunset views. The dock is on the east side (and has a bench) so it was a great place to watch the sunrise. We enjoyed spending time here and would welcome the chance to return. After full days of biking and sightseeing, this was a wonderful place to relax. Comfortable bed (with a great view of the water!), well-stocked kitchen, very nice sitting areas in the living room. Highly recommend!

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

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*Some exclusions may apply in certain geographies and for some properties.
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