Monthly Rentals in Tall Timbers

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

Nearby monthly rentals

Guest favorite
Cottage in Tall Timbers
4.89 out of 5 average rating, 122 reviews

Old World Cottage/Fabulous Sunsets/Polite Pets OK

JaniceRating, 5 stars1 month ago
Our stay in Tall Timbers was fabulous, much of it thanks to the care, detailed information, and lovely accommodations provided by our host, Robert. He communicated extremely well through the whole process from booking to check out. Nothing was a mystery and everything was as described or better. The house is charming and in a lovely wooded location. it's isolated but close to many amenities and short drive to historical attractions, local businesses, and the beautiful Maryland coast. We had a particularly wonderful visit to the Tall Timbers Oyster Ranch which is walking distance from the house. We highly recommend this location and send our thanks once again to Robert for his outstanding hospitality!
Superhost
Home in Hague
4.91 out of 5 average rating, 11 reviews

Riverside Dreams -golfcart-screened porch-views

Tony Rating, 5 stars2 weeks ago
cute little place. definitely will be coming back
Guest favorite
Cottage in Leonardtown
4.96 out of 5 average rating, 191 reviews

Beach Front and 'Perfectly Placed'

OlgaRating, 5 stars2 days ago
I don’t think I have enough words to describe how amazing Teresa’s place is! The photos don’t do it justice — it truly feels like a fairytale cottage. Every little detail is so thoughtfully planned. I’ve stayed at many Airbnbs, but this is by far the best one I’ve ever experienced. The cottage has everything you could possibly need — the kitchen is fully stocked, and the backyard is a dream. Having your own little private beach felt like paradise. We spent our mornings and evenings by the water, went kayaking, roasted marshmallows and sausages, and the kids had so much fun playing games. Teresa is an incredible host — she answered all my million questions with such kindness and patience. Even the neighbors were the sweetest people, which made everything feel even more special. We had the best five days there and will absolutely be back. Thank you, Teresa, for making our mini-vacation so magical and memorable!
Top guest favorite
Home in Hague
5 out of 5 average rating, 22 reviews

Rivah view get away

HollyRating, 5 stars2 weeks ago
We were in the area to explore George Washington’s Birthplace and Stratford hall and had a lovely stay at Susan’s place. The beds were comfortable, we cooked and sat on the front porch listening to the rain. The tavern is within walking distance but we didn’t get a chance to go. Hoping to come back again because the area is fabulous!

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

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Simple monthly prices

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

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