Vacation Rentals & Apartments in Chesapeake Beach

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51 apartments

24

Chesapeake Beach Apt. Walk to Bay, Beach & Marina!

Calvert County / Chesapeake Beach

Chesapeake Beach apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Air conditioning

Price per night from

$81

Responds fast!
avg. 45 minutes

Price per night from

$81

Great rentals within 20 miles that match your search

Distance approx 16.29 km from Chesapeake Beach

26

Annapolis Crows Nest Cottage: Chesapeake Bay View

Maryland / Annapolis

Annapolis villa

5 20 min stay varies

  • 5 bedrooms
  • sleeps 20
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Child Friendly

Price per night from

$797

Price per night from

$797

Distance approx 14.45 km from Chesapeake Beach

(3) Very Good 

36

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Talbot County / Wittman

Wittman log cabin

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool

Price per night from

$717

Price per night from

$717

Distance approx 16.11 km from Chesapeake Beach

(1) Excellent 

24

New! Beachfront 4BR St. Leonard Cottage w/ Deck!

Calvert County / St. Leonard

Saint Leonard cottage

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$185

Responds fast!
avg. 7 minutes

Price per night from

$185

Distance approx 16.62 km from Chesapeake Beach

55

Charming Annapolis home with stunning water views

Maryland / Annapolis

Annapolis house

4 11 5 nights min

  • 4 bedrooms
  • sleeps 11
  • 5 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$574

Price per night from

$574

Distance approx 16.75 km from Chesapeake Beach

25

Waterfront Stevensville House w/ Pier & 2 Decks!

Kent Island / Stevensville

Stevensville house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$430

Responds fast!
avg. 21 minutes

Price per night from

$430

Distance approx 10.14 km from Chesapeake Beach

24

Shady Side House on Chesapeake Bay Near Marina!

Maryland / Shady Side

Shady Side house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$213

Responds fast!
avg. 46 minutes

Price per night from

$213

Distance approx 2.72 km from Chesapeake Beach Show on Map

11

Panoramic Views of Herrington Harbour on the Bay.

Calvert County / North Beach

North Beach house

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$574

Price per night from

$574

Distance approx 11.75 km from Chesapeake Beach

32

A Special Occasion Property

Maryland / Croom

Croom house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$287

Responds fast!
avg. 41 minutes

Price per night from

$287

Distance approx 15.74 km from Chesapeake Beach

10

Harbor Cottage at the Chesapeake Bay

Calvert County / St. Leonard

Saint Leonard cottage

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$299

Price per night from

$299

Distance approx 18.16 km from Chesapeake Beach

(7) Very Good 

23

Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

Talbot County / St. Michaels

St. Michaels cottage

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$184

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$184

Distance approx 18.55 km from Chesapeake Beach

(2) Excellent 

18

Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX

Talbot County / St. Michaels

St. Michaels house

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$263

Price per night from

$263

Distance approx 18.18 km from Chesapeake Beach

(24) Excellent 

27

Location Location! St Michaels-- In Town Cottage!

Talbot County / St. Michaels

St. Michaels house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$172

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$172

Distance approx 19.57 km from Chesapeake Beach

18

Historic Waterfront Property with Wi-Fi and Dock

Talbot County / St. Michaels

St. Michaels house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$860

Responds fast!
avg. 3 hours 21 minutes

Price per night from

$860

Distance approx 18.2 km from Chesapeake Beach

(11) Very Good 

30

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

Talbot County / St. Michaels

St. Michaels house

7 9 min stay varies

  • 7 bedrooms
  • sleeps 9
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“Perfect in every way!” I stayed at the Thomas Harrison house a few weeks ago and all I can say is..."if you are planning on coming to St. Michael's you need to stay at this house." This house is perfect in every way. It has all the accommodations that
…see more

Price per night from

$333

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$333

Distance approx 19.26 km from Chesapeake Beach

(4) Excellent 

12

Gorgeous Hideaway: Spacious, Private, Huge Patio, Near DC

Maryland / Clinton

Clinton house

5 20 3 nights min

  • 5 bedrooms
  • sleeps 20
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$803

Price per night from

$803

Distance approx 13.52 km from Chesapeake Beach

(1) Excellent 

9

Cottage 2 at Grandview Pleasure Point

Talbot County / Bozman

Bozman house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$389

Price per night from

$389

Distance approx 1.57 km from Chesapeake Beach Show on Map

9

Renovated Luxury Waterview House

Calvert County / North Beach

North Beach house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly

Price per night from

$344

Price per night from

$344

Distance approx 12.83 km from Chesapeake Beach

(3) Excellent 

24

Best sunrise in St. Michaels....Broadview Bay House

Talbot County / St. Michaels

St. Michaels house

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$601

Price per night from

$601

Distance approx 13.65 km from Chesapeake Beach

8

Cottage 1a at Grandview Pleasure Point

Talbot County / Bozman

Bozman house

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

Price per night from

$281

Price per night from

$281

Distance approx 18.18 km from Chesapeake Beach

(3) Very Good 

25

Waterview Cottage In St. Michaels!

Talbot County / St. Michaels

St. Michaels cottage

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$184

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$184

Distance approx 13.65 km from Chesapeake Beach

6

Cottage 1b at Grandview Pleasure Point

Talbot County / Bozman

Bozman cottage

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$282

Price per night from

$282

Distance approx 13.48 km from Chesapeake Beach

(5) Excellent 

22

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

Talbot County / St. Michaels

St. Michaels house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$432

Price per night from

$432

Distance approx 19.74 km from Chesapeake Beach

15

Location,location,location,walk to city dock,free

Maryland / Annapolis

Annapolis apartment

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Car not necessary
  • Air conditioning
  • Private garden

Price per night from

$207

Price per night from

$207

Distance approx 15.5 km from Chesapeake Beach

12

Harris Cove Cottages LLC

Talbot County / St. Michaels

St. Michaels cottage

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$231

Price per night from

$231

Distance approx 19.81 km from Chesapeake Beach

24

Charming Artists Home in Eastport/Annapolis

Maryland / Annapolis

Annapolis house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Ask about children
  • Air conditioning

Price per night from

$430

Price per night from

$430

Distance approx 19.53 km from Chesapeake Beach

(2) Excellent 

52

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Maryland / Annapolis

Annapolis house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 6 mi
  • Child Friendly
  • Car not necessary

Price per night from

$287

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$287

Distance approx 18.3 km from Chesapeake Beach

7

St. Michael's Premier in Town Summer Cottage!

Talbot County / St. Michaels

St. Michaels house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$327

Price per night from

$327

Distance approx 13.52 km from Chesapeake Beach

(13) Excellent 

34

Main House at Grandview at Pleasure Point

Talbot County / Bozman

Bozman house

5 13 7 nights min

  • 5 bedrooms
  • sleeps 13
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool
“5 out of 5” I spent a long weekend at the main house, and it was easily the best weekend of the summer! The location is phenomenal. The house sits on large stretch of beautiful waterfront property. The views from the piers and the pool are exquisite.
…see more

Price per night from

$792

Price per night from

$792

Distance approx 19.64 km from Chesapeake Beach

23

Charming Eastport Home

Maryland / Annapolis

Annapolis house

3 8 5 nights min

  • 3 bedrooms
  • sleeps 8
  • 5 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$287

Price per night from

$287

Distance approx 19.84 km from Chesapeake Beach

(3) Very Good 

30

Beautiful Murray Hill Home (Annapolis)

Maryland / Annapolis

Annapolis house

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Ask about pets
“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decor
…see more

Price per night from

$488

Price per night from

$488

Distance approx 18.45 km from Chesapeake Beach

(1) Excellent 

18

Luxury Boat & Bed 78' Motor Yacht "Laid Off"

Maryland / Edgewater

Edgewater yacht

4 10 1 night min

  • 4 bedrooms
  • sleeps 10
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$1,134

Price per night from

$1,134

Distance approx 16.64 km from Chesapeake Beach

4

Lochhaven house for rent

Maryland / Edgewater

Edgewater house

3 2 7 nights min

  • 3 bedrooms
  • sleeps 2
  • 7 nights min
  • Air conditioning
  • Private garden

Price per night from

$116

Price per night from

$116

Distance approx 18.54 km from Chesapeake Beach

(1) Average 

38

St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

Talbot County / St. Michaels

St. Michaels villa

6 12 2 nights min

  • 6 bedrooms
  • sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 7 mi
  • Swimming pool

Price per night from

$1,147

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$1,147

Distance approx 17.48 km from Chesapeake Beach

6

One Beautiful home come relax

Maryland / Cheltenham

Cheltenham house

6 6 2 nights min

  • 6 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$201

Price per night from

$201

Distance approx 16.96 km from Chesapeake Beach

(2)  

26

3BR Annapolis Home on Oyster Creek w/Amazing Views

Maryland / Annapolis

Annapolis house

3 9 2 nights min

  • 3 bedrooms
  • sleeps 9
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$353

Responds fast!
avg. 14 minutes

Price per night from

$353

Distance approx 18.52 km from Chesapeake Beach

(5) Excellent 

17

KI Golf House-A PAR for the Course & Mile to Beach

Maryland / Kent Island

Kent Island house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 1 mi
  • Child Friendly
  • Air conditioning

Price per night from

$459

Responds fast!
avg. 1 hour 7 minutes

Price per night from

$459

Distance approx 18.34 km from Chesapeake Beach

9

Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina

Kent Island / Stevensville

Stevensville house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$478

Responds fast!
avg. 1 hour 7 minutes

Price per night from

$478

About Chesapeake Beach

The Chesapeake Bay region extends many miles into inland Maryland from the Atlantic Coast and is made up of all the towns that lie along the bay and its rivers and waterways. The towns in this area are diverse, but share a unique culture and centuries-old maritime history. The towns and metropolitan areas also share the bay itself and the natural beauty and riches that it offers, including the famous blue crab. Come to the Chesapeake Bay to experience cultural traditions, great museums, shipyards, and lighthouses. And while you're here, stay in a vacation rental of your own. Vacation rentals in this area are often less expensive than hotels. They are also more spacious and have better amenities, allowing you to relax in style as you plan your vacation adventures.

Wake up each morning in your bayside cottage or villa and enjoy a leisurely breakfast as birds call out from the delicate Chesapeake wetlands and marshes. Then head downtown to explore the shopping and historic strolling areas, go fishing, clamming or tide pooling in the bay, or relax on a pebbly beach. In the afternoon go for a hike or play a round of Chesapeake Bay golf. After a long day of exploring, head home to your vacation rental and host dinner for your friends and family on your rental's deck or light a fire and enjoy a night of Chesapeake Bay camping under the stars.

Here are a few additional suggestions:

  • Experience Chesapeake Bay sailing: Let the wind fill your sails and carry you out onto the waters of the bay in an authentic Chesapeake Bay Skipjack.
  • Enjoy a blue crab feast: Stop at a crab shack anywhere along the bay and bring home a barrel of real live blue crabs ready for steaming.
  • Go for a hike: Chesapeake Bay camping areas and hiking trails wind through the bluffs and sandy pine forest and offer beautiful views and great opportunities for bird watching.
  • Relax in a Chesapeake Bay spa: The spas in this area are legendary, and offer a perfect place to indulge in an afternoon of head-to-toe pampering.
  • Rent a bicycle: Pack a picnic lunch, rent a bicycle in town, and pedal along the boardwalk or through one of the rolling green parks around the bay area.
  • Tour a historic home: Almost every town along the bay can boast of streets and homes that have stood for centuries.
  • Explore a historic lighthouse: Preserved historic lighthouses, active working lighthouses, and lighthouse museums are a very important part of Chesapeake Bay history and culture.

The Chesapeake Bay is the perfect destination for history lovers, nature lovers, and those looking to take a romantic getaway or a unique family vacation. You'll never run out of fun things to do here, and the area is beautiful during all four seasons of the year. Get the most out of your visit by finding a vacation rental close to your favorite activities. While you're visiting the Chesapeake Bay, consider taking a trip to Washington, D.C. or the Delaware Bay to the north.