Holiday rentals in Galesville

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Top-rated holiday rentals in Galesville

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Cottage in Edgewater

4.99 out of 5 average rating, 122 reviews

Waterfront Chesapeake Bay Getaway Firepit & Pier!

Gorgeous sunrises from your completely remodeled waterfront cottage! Experience fresh Maryland Crabs or fish caught from your private pier & enjoy the peace, serenity and bay breezes from your furnished deck and green space. Enjoy true nature and explore Selby Bay on the South River with our complimentary canoe! Super clean with water views from kitchen, dining, living room & enclosed porch! Situated in a quiet neighborhood within 45 minutes of DC & 15 minutes from Annapolis & the Naval Academy.

11–18 Nov

€ 348 per night
Guest favourite

Home in Shady Side

5.0 out of 5 average rating, 113 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silverwater is a lesson in quiet luxury, compelling architecture, unimaginable views and endless comforts. Original fine art and luxe bedding envelope you in a modern, light-filled space. Outside you will be treated to an expansive waterfront lawn that is great for games and afternoon sun. Rest on modern lounges or watch the sunset on your private waterfront bluestone patio tucked into the sea grass. As a guest favorite, your fabulous getaway is here—just read the reviews!

18–25 Mar

€ 537 per night
Guest favourite

Flat in North Beach

4.97 out of 5 average rating, 100 reviews

Bayside Oasis of Southern Maryland

1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.

4–11 Nov

€ 136 per night

Popular amenities for Galesville holiday rentals

Other great holiday rentals in Galesville

Guest favourite

Home in Deale

4.98 out of 5 average rating, 111 reviews

Chesapeake Waterfront-Hot Tub-Kayaks-King Bed

8–15 Apr

€ 422 per night
Guest favourite

Cottage in North Beach

4.96 out of 5 average rating, 268 reviews

Waterfront Cottage Near Herrington and North Beach

1–8 May

€ 224 per night
Guest favourite

Home in Shady Side

4.97 out of 5 average rating, 64 reviews

Canary Pointe-A popular getaway for 2!

22–29 Dec

€ 190 per night
Guest favourite

Home in Shady Side

4.91 out of 5 average rating, 22 reviews

Baydream Believer -Chesapeake Bay water community

17–24 Dec

€ 265 per night
Guest favourite

Home in West River

4.97 out of 5 average rating, 71 reviews

Cozy waterview home in West River!

9–16 Oct

€ 300 per night
Guest favourite

Guest suite in Riva

5.0 out of 5 average rating, 7 reviews

Cozy one bedroom appt on the water

17–24 Jul

€ 94 per night
Guest favourite

Home in Shady Side

4.97 out of 5 average rating, 39 reviews

"Pier Joy!" - 3BR Waterfront Home W/Private Dock

18–25 Jun

€ 557 per night
Guest favourite

Home in Shady Side

5.0 out of 5 average rating, 16 reviews

The Cottage

25 Apr – 2 May

€ 319 per night
Guest favourite

Cottage in Shady Side

5.0 out of 5 average rating, 9 reviews

Tranquil Waterfront Cottage - 50 minutes to DC

28 Apr – 5 May

€ 394 per night
Guest favourite

Home in North Beach

4.86 out of 5 average rating, 58 reviews

Light of North Beach

15–22 Jul

€ 106 per night
Guest favourite

Home in Shady Side

4.96 out of 5 average rating, 52 reviews

Waterfront Sanctuary only 50 Min. From DC/Balt.

12–19 Dec

€ 706 per night
Guest favourite

Home in Annapolis

4.95 out of 5 average rating, 39 reviews

Naptown Suite

1–8 May

€ 108 per night

Destinations to explore