Cottage holiday rentals in Maryland
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Top-rated cottage rentals in Maryland
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for cottage rentals in Maryland
Cottage rentals with a hot tub
Cottage in North Beach
4.96 out of 5 average rating, 273 reviewsWaterfront Cottage Near Herrington and North Beach
26 Jul – 2 Aug
Cottage in Swanton
4.92 out of 5 average rating, 201 reviews*Deep Retreat* Fenced Dog Yard-Hot Tub-Fire Pit
15–22 Feb
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
16–23 Feb
Cottage in Oakland
4.95 out of 5 average rating, 185 reviewsPet-Friendly Cozy Home w/Hot Tub & Fire Pit
19–26 Jun
Cottage in Charlestown
4.98 out of 5 average rating, 55 reviewsLong Beach Cottage, (romantic couple’s getaway)
9–16 Oct
Cottage in Saint Leonard
4.98 out of 5 average rating, 92 reviewsHot Tub, Block to Beach, Fire Pit, Screened deck
27 Jun – 4 Jul
Cottage in Easton
5.0 out of 5 average rating, 83 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
6–13 Oct
Cottage in North East
5.0 out of 5 average rating, 47 reviewsCozy Cottage on the Chesapeake with Hot Tub
14–21 Mar
Pet-friendly cottage rentals
Cottage in Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
4–11 Oct
Cottage in Middletown
4.92 out of 5 average rating, 224 reviewsCharming "Cream of the Crop" Cape ~❤️of Middletown
4–11 Feb
Cottage in Berlin
4.99 out of 5 average rating, 119 reviewsBayfront Cottage w/ Amazing Views
20–27 Feb
Cottage in Westover
4.99 out of 5 average rating, 182 reviewsRumbley Cottage on the Tangier Sound-Private Beach
19–26 Dec
Cottage in Pasadena
4.97 out of 5 average rating, 158 reviewsFt. Smallwood Overlook. Waterfront with Kayaks!
7–14 Sept
Cottage in Saint Michaels
4.98 out of 5 average rating, 176 reviewsThe Little Anchor Cottage, St. Michaels, MD
30 Jan – 6 Feb
Cottage in Sharpsburg
4.86 out of 5 average rating, 101 reviewsPeaceful River House on Potomac- King Size Bed
8–15 Oct
Cottage in Annapolis
4.97 out of 5 average rating, 116 reviewsWaterfront farm retreat for vacation & telework
18–25 Mar
Private cottage rentals
Cottage in Leonardtown
4.91 out of 5 average rating, 149 reviewsPotomac Vista Cottage at Little Pond
27 Sept – 4 Oct
Cottage in Cambridge
4.98 out of 5 average rating, 108 reviewsChurch Creek - waterfront cottage & pool - private
31 Jan – 7 Feb
Cottage in Leonardtown
4.93 out of 5 average rating, 127 reviewsBreton Breeze
25 Oct – 1 Nov
Cottage in Aberdeen
4.95 out of 5 average rating, 148 reviewsTranquil Carriage House*MCM *Country *Wildlife
1–8 Apr
Cottage in Rock Hall
4.96 out of 5 average rating, 134 reviewsThe Blissful Retreat @theblissfulretreat
28 Nov – 5 Dec
Cottage in Smith Island
4.97 out of 5 average rating, 184 reviewsLevering Creek Cottage with Private Docking
10–17 Feb
Cottage in Leonardtown
4.93 out of 5 average rating, 193 reviewsPotomac River Freedom Cottage
1–8 Oct
Cottage in Saint Michaels
4.98 out of 5 average rating, 426 reviewsSt. Michaels-Historic Dist. Margaret Wells House
16–23 Mar
Destinations to explore
- Rentals with lake access Maryland
- Ski-in/ski-out rentals Maryland
- Family-friendly rentals Maryland
- House rentals Maryland
- Rentals with a kayak Maryland
- Rentals with an accessible-height bed Maryland
- Rentals with a patio Maryland
- Lakehouse rentals Maryland
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- Private suite rentals Maryland
- Flat rentals Maryland
- Farm stay rentals Maryland
- Rentals with a washing machine and dryer Maryland
- Rentals with a cinema Maryland
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- Aparthotel rentals Maryland
- Monthly Rentals Maryland
- Rentals with an EV charger Maryland
- Guest house rentals Maryland
- Fitness-friendly rentals Maryland
- Rentals with beach access Maryland
- Waterfront rentals Maryland
- Rentals with an accessible-height toilet Maryland
- Pet-friendly rentals Maryland
- Rentals with a hot tub Maryland
- Rentals with a sauna Maryland
- Rentals with outdoor seating Maryland
- Smoking-friendly rentals Maryland
- Rentals with a fireplace Maryland
- Wheelchair-accessible rentals Maryland
- Cabin rentals Maryland
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