Chesapeake Bay vacation rentals

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Top-rated vacation rentals in Chesapeake Bay

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

Guest favorite

Home in Chestertown

4.94 out of 5 average rating, 127 reviews

CHESAPEAKE SUNSETS

Escape to a quaint bayside cottage with sweeping views of the Chesapeake. Relax and enjoy beautiful sunsets from the bayside sundeck, screened porch or from the comfort of your home. Less than 2 miles to the seasonal Shanty Bar at Tolchester Marina featuring live music, dining and its own beach. One mile from a private community boat ramp to launch your water toys. 800 sq ft 2 bedroom 1 bath house is on Maryland’s Eastern Shore less than 2 hours from Washington, Baltimore and Philadelphia.

Aug 7 – 14

R3,722 ZAR per night
Guest favorite

Farm stay in Madison

4.98 out of 5 average rating, 159 reviews

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

Oct 22 – 29

R2,343 ZAR per night
Guest favorite

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 292 reviews

Historic St.Mary's City at the Lazy Bear Cottage

Inquire first on pets, there is a 40 lb. weight limit total, can be split up between 2 small dogs or 1 at 40lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

Oct 5 – 12

R1,564 ZAR per night

Popular amenities for Chesapeake Bay vacation rentals

Chesapeake Bay waterfront vacation rentals

Guest favorite

Cottage in Onancock

4.97 out of 5 average rating, 191 reviews

Waterfront romantic getaway Eastern Shore w dock

Sep 26 – Oct 3

R3,422 ZAR per night
Guest favorite

Farm stay in Onancock

4.99 out of 5 average rating, 167 reviews

Private romantic pet friendly waterfront cottage

Nov 24 – Dec 1

R3,376 ZAR per night
Guest favorite

Cottage in Westover

4.99 out of 5 average rating, 178 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Dec 7 – 14

R6,383 ZAR per night
Guest favorite

Guesthouse in Stevensville

5.0 out of 5 average rating, 202 reviews

Waterfront Getaway - View of bay from your bed

Apr 17 – 24

R4,994 ZAR per night
Guest favorite

Farm stay in Chestertown

4.93 out of 5 average rating, 121 reviews

Blue Heron Farm Waterfront Chalet

Dec 17 – 24

R5,807 ZAR per night
Guest favorite

Cottage in Heathsville

4.94 out of 5 average rating, 175 reviews

HedgeRow, Deer Haven in the NNK- Dock & Boat Ramp

Jan 18 – 25

R2,384 ZAR per night
Guest favorite

Cottage in Leonardtown

4.97 out of 5 average rating, 120 reviews

Beach Front and 'Perfectly Placed'

Oct 9 – 16

R2,994 ZAR per night
Guest favorite

Home in Reedville

4.97 out of 5 average rating, 115 reviews

Sunkissed Cottage-private, natural waterfront home

Sep 6 – 13

R2,797 ZAR per night
Guest favorite

Cottage in Kinsale

4.95 out of 5 average rating, 187 reviews

Great little cottage with a "Rivah" view

Feb 18 – 25

R2,812 ZAR per night
Guest favorite

Guest suite in Berlin

4.97 out of 5 average rating, 527 reviews

Ayers Creek Carriage House

Apr 18 – 25

R2,300 ZAR per night
Guest favorite

Cottage in Saint Michaels

4.99 out of 5 average rating, 136 reviews

La Casita on Harris Creek, St. Michaels

Aug 1 – 8

R10,581 ZAR per night
Guest favorite

Cottage in Saint Leonard

4.99 out of 5 average rating, 101 reviews

Captain Jack's Bay Hideaway

Oct 25 – Nov 1

R2,922 ZAR per night

Chesapeake Bay fishing vacation rentals

Guest favorite

Apartment in Frederica

4.96 out of 5 average rating, 253 reviews

Smokefree Lakeside Relaxation

Dec 16 – 23

R1,407 ZAR per night
Guest favorite

Tiny home in Cape Charles

4.98 out of 5 average rating, 268 reviews

The Laughing King Retreat Honeymoon Island Cottage

Dec 30 – Jan 6

R4,878 ZAR per night
Guest favorite

Cabin in Lusby

4.91 out of 5 average rating, 203 reviews

Peaceful Waterfront Retreat on The Bay

Oct 22 – 29

R3,114 ZAR per night
Guest favorite

Farm stay in Cardinal

4.95 out of 5 average rating, 104 reviews

Wtrfrnt aptmnt w/pool/dock on private farm

Oct 7 – 14

R2,612 ZAR per night
Superhost

Tiny home in Cambridge

4.89 out of 5 average rating, 492 reviews

Blackwater Tiny Cabin on Snakehead Creek

Jul 7 – 14

R1,623 ZAR per night
Guest favorite

Guesthouse in Saluda

4.93 out of 5 average rating, 463 reviews

Wooded Cabin retreat on fresh water pond

Apr 11 – 18

R1,877 ZAR per night
Guest favorite

Guest suite in Piney Point

4.94 out of 5 average rating, 222 reviews

Spectacular beachfront walk-out in Piney Point MD

Jul 6 – 13

R8,441 ZAR per night
Guest favorite

Loft in Cape May Court House

4.97 out of 5 average rating, 583 reviews

Quiet Lakefront Studio - Close to the Beach

Nov 20 – 27

R2,526 ZAR per night
Guest favorite

Guesthouse in Church Road

5.0 out of 5 average rating, 130 reviews

Heron Rock: Lakefront Cottage on Lake Chesdin

Aug 14 – 21

R2,525 ZAR per night
Guest favorite

Guest suite in Lusby

4.99 out of 5 average rating, 299 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

Mar 19 – 26

R2,542 ZAR per night
Guest favorite

Apartment in Stevensville

4.97 out of 5 average rating, 239 reviews

Boutique by the Bay

Aug 17 – 24

R3,762 ZAR per night
Guest favorite

Guesthouse in Lusby

4.97 out of 5 average rating, 131 reviews

Cozy Lakeside Studio Retreat.

Aug 24 – 31

R2,457 ZAR per night

Chesapeake Bay cottage rentals

Guest favorite

Cottage in Westover

4.92 out of 5 average rating, 140 reviews

Heaven on the Bay - A Peaceful Waterfront Retreat

May 10 – 17

R4,605 ZAR per night
Guest favorite

Cottage in Gloucester

4.97 out of 5 average rating, 190 reviews

"Bee Haven" Cottage Retreat

Mar 6 – 13

R2,304 ZAR per night
Guest favorite

Cottage in Stevensville

4.94 out of 5 average rating, 130 reviews

Cottage on the Bay - Kent Island

Apr 3 – 10

R7,178 ZAR per night
Superhost

Cottage in Reedville

4.9 out of 5 average rating, 156 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

Jan 29 – Feb 5

R6,163 ZAR per night
Guest favorite

Cottage in Colonial Beach

4.93 out of 5 average rating, 177 reviews

Cozy cottage 3 blocks from beach

Jan 13 – 20

R2,319 ZAR per night
Guest favorite

Cottage in Norfolk

4.98 out of 5 average rating, 263 reviews

Lovely Ocean View Cottage

Feb 5 – 12

R2,392 ZAR per night
Guest favorite

Cottage in Leonardtown

4.91 out of 5 average rating, 148 reviews

Potomac Vista Cottage at Little Pond

Aug 16 – 23

R3,083 ZAR per night
Guest favorite

Cottage in Urbanna

4.99 out of 5 average rating, 134 reviews

Little Dipper -private beach,Kayaks & paddleboards

Oct 14 – 21

R3,933 ZAR per night
Guest favorite

Cottage in Leonardtown

4.93 out of 5 average rating, 193 reviews

Potomac River Freedom Cottage

Sep 9 – 16

R4,010 ZAR per night
Guest favorite

Cottage in Gloucester Courthouse

4.99 out of 5 average rating, 192 reviews

Historic Ware River Cottage at Glebefield

Jan 12 – 19

R3,121 ZAR per night
Guest favorite

Cottage in Ashland

4.95 out of 5 average rating, 240 reviews

The Cottage at Walnut Shade

Jun 12 – 19

R2,628 ZAR per night
Guest favorite

Cottage in Edgewater

4.99 out of 5 average rating, 123 reviews

Waterfront Chesapeake Bay Getaway Firepit & Pier!

Jan 21 – 28

R6,084 ZAR per night

Destinations to explore