Title: Dorchester County Cottages from CA $398 | Expedia.ca

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976431085&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=553248635976431085&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976431085&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976431085&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Cities in Dorchester County

![](https://images.trvl-media.com/place/6608/8ce19001-5246-4d03-a239-330291c6972a.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Cambridge

[](https://expedia.ca/Cambridge-Cottages.d6608-aaCottages.Travel-Guide-Accommodation)

![Aerial panorama of Chesapeake City Maryland historic fishing town on the Chesapeake Delaware canal with private boats docked in the marina and the Chesapeake City Bridge over the back creek](https://images.trvl-media.com/place/3000440577/90bee61b-a5b7-4d81-9610-7af49a80c495.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Fishing Creek

[](https://expedia.ca/Fishing-Creek-Cottages.d3000440577-aaCottages.Travel-Guide-Accommodation)

![](https://images.trvl-media.com/place/3000440559/e7920e1b-cd27-48f3-a248-1e2775cca9b0.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### East New Market

[](https://expedia.ca/East-New-Market-Cottages.d3000440559-aaCottages.Travel-Guide-Accommodation)

![Birds - Cattle Egret, Blackwater National Wildlife Refuge, Virginia](https://images.trvl-media.com/place/553248635975865928/dbd6d7b0-c9d1-4118-b96f-516a26296cfd.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Woolford

[](https://expedia.ca/Woolford-Cottages.d553248635975865928-aaCottages.Travel-Guide-Accommodation)

## Our top choices for Dorchester County cottages

![Exterior](https://images.trvl-media.com/lodging/35000000/34590000/34583000/34582947/b1486943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34590000/34583000/34582947/3b8e0d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34590000/34583000/34582947/467a4674.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/35000000/34590000/34583000/34582947/6d256c87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

[](https://www.expedia.ca/St-Michaels-Hotels-Carpenter-St-Cottage-In-The-Heart-Of-St-Michaels-Village-Large-Screened-Porch.h34582947.Hotel-Information)

Downtown St. Michaels

9.8/10

Exceptional

(200 reviews)

"Perfect house close to St Michael’s attractions"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carolyn E.

[](https://www.expedia.ca/St-Michaels-Hotels-Carpenter-St-Cottage-In-The-Heart-Of-St-Michaels-Village-Large-Screened-Porch.h34582947.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/99000000/98520000/98514500/98514456/97767946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/99000000/98520000/98514500/98514456/40497eda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/99000000/98520000/98514500/98514456/081634c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/99000000/98520000/98514500/98514456/f1bc6e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### "Point of View" Waterfront cottage with panoramic views on Tilghman Island

[](https://www.expedia.ca/Tilghman-Hotels-Waterfront-Cottage-With-Panoramic-Views-On-Tilghman-Island.h98514456.Hotel-Information)

Tilghman Island

10/10

Exceptional

(15 reviews)

"Amazing property well presented with fantastic views in all directions"

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

David G.

[](https://www.expedia.ca/Tilghman-Hotels-Waterfront-Cottage-With-Panoramic-Views-On-Tilghman-Island.h98514456.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/23000000/22130000/22121200/22121103/cc3a9f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/23000000/22130000/22121200/22121103/61116c9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/23000000/22130000/22121200/22121103/c090e0f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/23000000/22130000/22121200/22121103/182d2430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

[](https://www.expedia.ca/Scotland-Hotels-Enjoy-The-Hideaway-In-Hays-Beach-On-Chesapeake-Bay-With-Internet-301-250-8384.h22121103.Hotel-Information)

Point Lookout

10/10

Exceptional

(126 reviews)

"Hideaway at Hayes Beach was amazing It was a wonderful place to spend Christmas with our family. We were lucky enough to get snow! My husband and I enjoy walking so it was a prefect place to for it. Would definitely recommend this place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

April T.

CA $349

CA $745 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Scotland-Hotels-Enjoy-The-Hideaway-In-Hays-Beach-On-Chesapeake-Bay-With-Internet-301-250-8384.h22121103.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33506200/33506110/1dc9ddc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor banquet area](https://images.trvl-media.com/lodging/34000000/33510000/33506200/33506110/d6f3062d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/34000000/33510000/33506200/33506110/c5d1df22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33510000/33506200/33506110/4cbad302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family and Pet-Friendly, Waterfront with Pier

[](https://www.expedia.ca/Cambridge-Hotels-Family-And-Pet-Friendly.h33506110.Hotel-Information)

Cambridge

10/10

Exceptional

(265 reviews)

"The hosts were very welcoming, helpful, good communication throughout the reservation process and stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ann R.

[](https://www.expedia.ca/Cambridge-Hotels-Family-And-Pet-Friendly.h33506110.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/98000000/97090000/97083900/97083848/4ad81af5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/98000000/97090000/97083900/97083848/02bfe381.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/98000000/97090000/97083900/97083848/7de24981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97090000/97083900/97083848/1292e208.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

[](https://www.expedia.ca/Stevensville-Hotels-Accessible.h97083848.Hotel-Information)

Stevensville

10/10

Exceptional

(63 reviews)

"great stay ! all needs where met . "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

randall j.

[](https://www.expedia.ca/Stevensville-Hotels-Accessible.h97083848.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/afb23ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/9cea1d1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/c9d30e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/811a0e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

[](https://www.expedia.ca/St-Michaels-Hotels-John-Bruff-Waterview-Cottage-On-Harbor-And-On-Park-In-Town-St-Michaels.h32562385.Hotel-Information)

Downtown St. Michaels

9.6/10

Exceptional

(126 reviews)

"Ideal location to shops and attractions. Host very easy to reach. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Don N.

[](https://www.expedia.ca/St-Michaels-Hotels-John-Bruff-Waterview-Cottage-On-Harbor-And-On-Park-In-Town-St-Michaels.h32562385.Hotel-Information)

![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/71000000/70480000/70478400/70478395/f91c2daf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/71000000/70480000/70478400/70478395/74758364.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/71000000/70480000/70478400/70478395/93712141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/71000000/70480000/70478400/70478395/fda5f50c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

[](https://www.expedia.ca/Lusby-Hotels-Welcome-To-The-Boathouse-On-Mill-Creek.h70478395.Hotel-Information)

Lusby

10/10

Exceptional

(55 reviews)

"Incredible property and stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hunter B.

[](https://www.expedia.ca/Lusby-Hotels-Welcome-To-The-Boathouse-On-Mill-Creek.h70478395.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/99000000/98530000/98524500/98524460/7ce77c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/99000000/98530000/98524500/98524460/496cd8f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/99000000/98530000/98524500/98524460/9f38452e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/99000000/98530000/98524500/98524460/311ee870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 Bedroom Cozy Beach Cottage with Water Access

[](https://www.expedia.ca/Piney-Point-Hotels-2-Bedroom-Cozy-Beach-Cottage-With-Water-Access.h98524460.Hotel-Information)

Piney Point

9.6/10

Exceptional

(22 reviews)

"Great place to stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sean H.

[](https://www.expedia.ca/Piney-Point-Hotels-2-Bedroom-Cozy-Beach-Cottage-With-Water-Access.h98524460.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/20000000/19450000/19447700/19447633/c4596021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19450000/19447700/19447633/0fa1b011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/20000000/19450000/19447700/19447633/0a6ceb69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19450000/19447700/19447633/f7cccf1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relaxing Waterfront Cottage Near St Michaels, Maryland

[](https://www.expedia.ca/Wittman-Hotels-Relaxing-Waterfront-Cottage-Near-St-Michaels.h19447633.Hotel-Information)

Wittman

9.8/10

Exceptional

(241 reviews)

"A cozy cottage, definitely met our needs. Beautiful view!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cynthia Louise C.

[](https://www.expedia.ca/Wittman-Hotels-Relaxing-Waterfront-Cottage-Near-St-Michaels.h19447633.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/94000000/93250000/93249900/93249890/w1014h683x5y0-3c9c9ed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/94000000/93250000/93249900/93249890/7204ef41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93250000/93249900/93249890/w1013h683x5y0-5da62d36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/94000000/93250000/93249900/93249890/w509h683x258y0-5a07a91d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Soul Oasis - home on the Chesapeake Bay

[](https://www.expedia.ca/Lusby-Hotels-Soul-Oasis-Home-On-The-Chesapeake-Bay.h93249890.Hotel-Information)

Lusby

10/10

Exceptional

(43 reviews)

"The guidebook binder at the property helpfully had details about the Soul Oasis, like how to operate the heaters and fireplace, and suggested local spots and restaurants to visit. Also, the kitchen conveniently had many pots and pans and tools. The view of the water was a highlight!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bronwen C.

CA $174

CA $398 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Lusby-Hotels-Soul-Oasis-Home-On-The-Chesapeake-Bay.h93249890.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/113000000/112360000/112353400/112353391/63e9fddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112360000/112353400/112353391/02fc5278.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112360000/112353400/112353391/1233b0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112360000/112353400/112353391/5ebbe8b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

[](https://www.expedia.ca/Scotland-Hotels-Cozy-Sunrise-Waterfront-2-Bedroom-Cottage-Dock-Serene-Point-LookoutScotland.h112353391.Hotel-Information)

Point Lookout

9.4/10

Exceptional

(12 reviews)

"Pet friendly, easy check out, no cleaning involved."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Naomi B.

CA $328

CA $634 total

includes taxes & fees

Apr 10 - Apr 11

[](https://www.expedia.ca/Scotland-Hotels-Cozy-Sunrise-Waterfront-2-Bedroom-Cottage-Dock-Serene-Point-LookoutScotland.h112353391.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33506400/33506340/94b7abde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/34000000/33510000/33506400/33506340/24988e07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33510000/33506400/33506340/64e8901b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/34000000/33510000/33506400/33506340/e90c2a10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

[](https://www.expedia.ca/Churchton-Hotels-Watrfnt-Cottage-ChesapeakeParadise-KayaksDogs-OK.h33506340.Hotel-Information)

Deale

9.8/10

Exceptional

(83 reviews)

"The cottage was a wonderful place for me and my kids to stay. I really appreciate the thoughtfulness of the owner. We would definitely stay here again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Paul M.

[](https://www.expedia.ca/Churchton-Hotels-Watrfnt-Cottage-ChesapeakeParadise-KayaksDogs-OK.h33506340.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/21000000/20180000/20178900/20178804/d9a98d15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/21000000/20180000/20178900/20178804/f77f6755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/21000000/20180000/20178900/20178804/d6988f99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/21000000/20180000/20178900/20178804/056d85bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Intown Cottage – The Ultimate Walkable Getaway steps from Downtown!

[](https://www.expedia.ca/St-Michaels-Hotels-Cottage-Downtown-On-A-Quiet-Street.h20178804.Hotel-Information)

Downtown St. Michaels

9.8/10

Exceptional

(59 reviews)

"It's a very nice place and the location is great. Its not a professionally managed house which is fine, but we didn't know that going in. Everything is clean, but not professionally clean i.e. the sheets are clean but the mattress pad was not. I would stay there again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Casey G.

[](https://www.expedia.ca/St-Michaels-Hotels-Cottage-Downtown-On-A-Quiet-Street.h20178804.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/83000000/82510000/82500500/82500466/0b4ed257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/83000000/82510000/82500500/82500466/aaf850da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/83000000/82510000/82500500/82500466/4323286a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/83000000/82510000/82500500/82500466/d7791c89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### BEACH COTTAGE BY THE SEA....

[](https://www.expedia.ca/Reedville-Hotels-Beach-Cottage-By-The-Sea.h82500466.Hotel-Information)

Reedville

10/10

Exceptional

(32 reviews)

"The house is small, but works great for a getaway and has everything you need. We spent most of our time at the beach or on the deck -- so peaceful! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robin B.

[](https://www.expedia.ca/Reedville-Hotels-Beach-Cottage-By-The-Sea.h82500466.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/71000000/70330000/70321000/70320929/b4754bf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/71000000/70330000/70321000/70320929/24cacafd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/71000000/70330000/70321000/70320929/69296e8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/71000000/70330000/70321000/70320929/27a68a3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### "Dragonfly" Waterfront Cottage on Chesapeake Bay

[](https://www.expedia.ca/Reedville-Hotels-Dragonfly-Waterfront-Cottage-On-Chesapeake-Bay.h70320929.Hotel-Information)

Reedville

10/10

Exceptional

(3 reviews)

"Great getaway location right on th4e water. Highly recommended"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

James P.

[](https://www.expedia.ca/Reedville-Hotels-Dragonfly-Waterfront-Cottage-On-Chesapeake-Bay.h70320929.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71950000/71943900/71943863/2bdce496.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis](https://images.trvl-media.com/lodging/72000000/71950000/71943900/71943863/2e0b6764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943900/71943863/7d640bf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/72000000/71950000/71943900/71943863/6e7af421.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

[](https://www.expedia.ca/Lottsburg-Hotels-Relax-And-Renew-At-Ruppert-Cottage-Right-On-The-Water-With-Private-Pier.h71943863.Hotel-Information)

Lottsburg

10/10

Exceptional

(63 reviews)

"Wonderful property stocked full of anything you would need for a great vacation. We had a great time! Thank you!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cody G.

[](https://www.expedia.ca/Lottsburg-Hotels-Relax-And-Renew-At-Ruppert-Cottage-Right-On-The-Water-With-Private-Pier.h71943863.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/56000000/55190000/55185300/55185255/d2a82a1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/56000000/55190000/55185300/55185255/fa69d16e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/56000000/55190000/55185300/55185255/71450498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/56000000/55190000/55185300/55185255/f765d945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, ON THE SANDS OF THE 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

[](https://www.expedia.ca/Scotland-Hotels-BAY-SIDE-RETREAT-HAYS-BEACH-RIGHT-ON-THE-SANDS-OF-THE-CHESAPEAKE-BAY.h55185255.Hotel-Information)

Point Lookout

10/10

Exceptional

(125 reviews)

"Perfect place for a quiet getaway at the beach!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cheryl S.

[](https://www.expedia.ca/Scotland-Hotels-BAY-SIDE-RETREAT-HAYS-BEACH-RIGHT-ON-THE-SANDS-OF-THE-CHESAPEAKE-BAY.h55185255.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118330000/118328600/118328596/3459c21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118330000/118328600/118328596/d0b24e3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118330000/118328600/118328596/765d1959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/119000000/118330000/118328600/118328596/59779c39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC

[](https://www.expedia.ca/Royal-Oak-Hotels-Spacious-6-Bedroom-Cottage-In-Charming-Royal-Oak-With-WiFi.h118328596.Hotel-Information)

Royal Oak

[](https://www.expedia.ca/Royal-Oak-Hotels-Spacious-6-Bedroom-Cottage-In-Charming-Royal-Oak-With-WiFi.h118328596.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/33000000/32600000/32590200/32590170/831e4185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32600000/32590200/32590170/802a1be9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/33000000/32600000/32590200/32590170/w1919h1440x1y0-13f44413.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32600000/32590200/32590170/22b0e30e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

[](https://www.expedia.ca/St-Michaels-Hotels-Location.h32590170.Hotel-Information)

Downtown St. Michaels

9.4/10

Exceptional

(130 reviews)

"Our dog was so comfortable and welcome at this rental!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kathie F.

[](https://www.expedia.ca/St-Michaels-Hotels-Location.h32590170.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/77000000/76790000/76789900/76789882/34ce992e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76790000/76789900/76789882/28733640.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76790000/76789900/76789882/fb50c822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76790000/76789900/76789882/3bf7bc2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

[](https://www.expedia.ca/Serene-Spot.h76789882.Hotel-Information)

West River

9.8/10

Exceptional

(43 reviews)

"This was such a beautiful property right on the water! It was everything I wanted for a quiet weekend away. The host was quick to respond and full of great recommendations. I am definitely planning on staying here again and will recommend it to anyone else 10/10"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Meghan G.

[](https://www.expedia.ca/Serene-Spot.h76789882.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-04-18&endDate=2026-04-19&regionId=553248635976431085&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Dorchester+County%2C+Maryland%2C+United+States+of+America&regionId=553248635976431085&latLong=38.571462%2C-76.076318&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Dorchester+County%2C+Maryland%2C+United+States+of+America&regionId=553248635976431085&latLong=38.571462%2C-76.076318&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Dorchester+County%2C+Maryland%2C+United+States+of+America&regionId=553248635976431085&latLong=38.571462%2C-76.076318&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=CONDO)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Dorchester+County%2C+Maryland%2C+United+States+of+America&regionId=553248635976431085&latLong=38.571462%2C-76.076318&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=APARTMENT)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Dorchester+County%2C+Maryland%2C+United+States+of+America&regionId=553248635976431085&latLong=38.571462%2C-76.076318&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=CABIN)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Dorchester+County%2C+Maryland%2C+United+States+of+America&regionId=553248635976431085&latLong=38.571462%2C-76.076318&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=HOUSE_BOAT)

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## Top Dorchester County Hotel Reviews

![Inn at Perry Cabin](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/12b2f8fd_y.jpg)

### Inn at Perry Cabin

10/10 Excellent

"An excellent venue from start to finish. The staff are super polite and friendly, service is excellent and the property is clean and very well kept, both inside and out. Food quality is great. We had one issue with in-room dining, where the QR code to access the menu didn't bring up the right menu, so an order we placed wasn't correct. It was immediately addressed and the item comped, which whilst not necessary, was very welcome. I would definitely recommend the hotel to anyone and will be back.."

[](https://expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information)

![Country Inn & Suites by Radisson, Salisbury, MD](https://images.trvl-media.com/lodging/2000000/1260000/1250200/1250138/6d882304_y.jpg)

### Country Inn & Suites by Radisson, Salisbury, MD

8/10 Good

"Breakfast was basic but fine"

[](https://expedia.ca/Salisbury-Hotels-Country-Inn-Suites-By-Radisson.h1250138.Hotel-Information)

![Wingate by Wyndham Salisbury](https://images.trvl-media.com/lodging/1000000/220000/213700/213687/c4e09781_y.jpg)

### Wingate by Wyndham Salisbury

6/10 Okay

"Parking was easy, check in was quick and efficient. The room was OK for a one night stay. I didn’t like that there were no inputs for my electronic cords; i had to use the bricks for my electronics and the sockets on the lamps by the bed were loose so my charging brick wouldn’t stay in. The TV remote had the Netflix button but when i pressed it the TV didn’t have Netflix which was a little disappointing bc i don’t watch cable. Otherwise i had a decent night. I had to be out early so i didn’t get to try the breakfast but it smelled really good."

[](https://expedia.ca/Salisbury-Hotels-Sleep-Inn-Salisbury.h213687.Hotel-Information)

![Days Inn by Wyndham Salisbury](https://images.trvl-media.com/lodging/1000000/20000/16300/16257/05326d34_y.jpg)

### Days Inn by Wyndham Salisbury

8/10 Good

"Parking and check in easy and secure. "

[](https://expedia.ca/Salisbury-Hotels-Days-Inn-By-Wyndham-Salisbury.h16257.Hotel-Information)

![The Wildset](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/391fbabf_y.jpg)

### The Wildset

10/10 Excellent

"Cute place "

[](https://expedia.ca/St-Michaels-Hotels-The-Wildset.h64410566.Hotel-Information)

![St Michaels Inn](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg)

### St Michaels Inn

10/10 Excellent

"Friendly staff. Wonderful location. Overall it was great!"

[](https://expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information)

![Hampton Inn Salisbury](https://images.trvl-media.com/lodging/1000000/290000/282000/281943/633fd984_y.jpg)

### Hampton Inn Salisbury

8/10 Good

"The hotel was fine but I was extremely disappointed that I paid for a room with a King bed and was given a room with 2 smaller beds. "

[](https://expedia.ca/Salisbury-Hotels-Hampton-Inn-Salisbury.h281943.Hotel-Information)

![The Tidewater Inn](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/1969a1ee_y.jpg)

### The Tidewater Inn

10/10 Excellent

"The room was clean and the staff was delightful"

[](https://expedia.ca/Easton-Hotels-The-Tidewater-Inn.h1105532.Hotel-Information)

![Comfort Inn & Suites Lexington Park near Pax River](https://images.trvl-media.com/lodging/6000000/5100000/5098400/5098394/11804ad4_y.jpg)

### Comfort Inn & Suites Lexington Park near Pax River

6/10 Okay

"AC was very noisy. Room was rather drab. For the price I definitely expected better. "

[](https://expedia.ca/Lexington-Park-Hotels-Comfort-Inn-Suites.h5098394.Hotel-Information)

## Find out more about Dorchester County

## Dorchester County Cottages information

| Number of reviews | 1,651        |
| ----------------- | ------------ |
| Accommodation     | 179 Cottages |
| Lowest Price      | CA $398      |
| Highest Price     | CA $745      |

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- [Hotels near Choptank River Lighthouse ](https://www.expedia.ca/Choptank-River-Lighthouse-Hotels.0-l6286144-0.Travel-Guide-Filter-Hotels)
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- [Flights to Cambridge ](https://www.expedia.ca/Cheap-Flights-To-Cambridge.d6608.Travel-Guide-Flights)
- [Flights from Toronto (YYZ) to Cambridge (CGE) ](https://www.expedia.ca/lp/flights/yyz/cge/toronto-to-cambridge)

- [Bill Burton Fishing Pier State Park ](https://www.expedia.ca/Bill-Burton-Fishing-Pier-State-Park-Trappe.d553248633992438879.Vacation-Attraction)
- [Brannock Maritime Museum ](https://www.expedia.ca/Brannock-Maritime-Museum-Cambridge.d553248621532662096.Vacation-Attraction)
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- [Long Wharf Park ](https://www.expedia.ca/Long-Wharf-Park-Cambridge.d6286116.Vacation-Attraction)

- [Car rental Cambridge ](https://www.expedia.ca/Car-Rentals-In-Cambridge.d6608.Car-Rental-Guide)
- [National Car Rental Rental Cars in Cambridge ](https://www.expedia.ca/National-Car-Rental-Car-Rentals-In-Cambridge.d6608-c42.Car-Rental-Guide-Suppliers)
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- [Book Cottages in Dorchester County on Expedia.com ](https://www.expedia.com/Dorchester-County-Cottages.d553248635976431085-aaCottages.Travel-Guide-Accommodation)