House vacation rentals in Chestertown
Find and book unique houses on Airbnb
Top-rated house rentals in Chestertown
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chestertown house rentals
House rentals with a pool
Home in Chestertown
5 out of 5 average rating, 21 reviewsChestertown Watson Family Farm
Home in Edgewater
4.92 out of 5 average rating, 138 reviewsHouse in Edgewater Maryland
Home in Queenstown
4.81 out of 5 average rating, 155 reviewsBay Breeze Retreat
Home in Rock Hall
4.94 out of 5 average rating, 35 reviewsRockfish Keeper
Home in Chester
4.99 out of 5 average rating, 80 reviewsWaterfront Farmhouse Meets Modern Luxury
Home in Perry Hall
4.99 out of 5 average rating, 81 reviewsGunpowder Retreat
Home in Shady Side
4.88 out of 5 average rating, 181 reviewsCattail Landing- Photographer's Waterfront Retreat
Home in Clayton
5 out of 5 average rating, 19 reviewsThe Hidden Gem•Heated pool•Pickleball Court
Weekly house rentals
Home in Chestertown
4.97 out of 5 average rating, 86 reviewsRiver front cottage with private dock & water fun
Home in Rock Hall
4.98 out of 5 average rating, 47 reviewsEastern Neck Water Paradise w/Brick oven & Beach
Home in Chestertown
4.94 out of 5 average rating, 36 reviewsWaterfront Paradise w/ Pier - kayak to Chestertown
Home in Chestertown
4.97 out of 5 average rating, 29 reviewsRiver Cottage, Chestertown
Home in Millington
4.96 out of 5 average rating, 26 reviewsLark's Nest on the Chester River
Home in Greensboro
4.96 out of 5 average rating, 76 reviewsCozy 2 bedroom home on wooded private lane
Home in Chestertown
5 out of 5 average rating, 34 reviewsMagnolia House: walk to shops, restaurants, river
Home in Chestertown
5 out of 5 average rating, 33 reviewsIn Town Chestertown Rancher (1 Block to College)
Private house rentals
Home in Chestertown
4.96 out of 5 average rating, 24 reviewsQuiet, Shabby-chic home in downtown Chestertown
Home in Galena
4.95 out of 5 average rating, 21 reviewsConnection Pointe•River views•Quiet•Peaceful
Home in Rock Hall
5 out of 5 average rating, 26 reviews1-Particular Harbor: A Coastal Oasis!
Home in Betterton
5 out of 5 average rating, 35 reviewsRuby's Sea Glass Cottage near Betterton Beach
Home in Chestertown
4.92 out of 5 average rating, 51 reviewsEastern Shore Hideaway Deck, Kayaks, Grill, & Pit
Home in Kennedyville
4.93 out of 5 average rating, 54 reviewsComfy and Cozy on the Eastern Shore
Home in Rock Hall
5 out of 5 average rating, 90 reviewsCozy 1920's Bungalow Near Water/Local Attractions
Home in Rock Hall
4.97 out of 5 average rating, 35 reviewsEastern Shore Escape in the Heart of Rock Hall
Quick stats about house rentals in Chestertown
Total rentals
20 properties
Total number of reviews
1.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Destinations to explore
- Baltimore Vacation rentals
- Ocean City Vacation rentals
- Atlantic City Vacation rentals
- Cape May Vacation rentals
- Wildwood Vacation rentals
- Rehoboth Beach Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Lighthouse rentals United States
- Guesthouse rentals United States
- Earth house rentals United States
- Townhouse rentals United States
- House rentals United States
- House rentals Washington
- Lakehouse rentals Washington
- Guesthouse rentals Washington
- Townhouse rentals Washington
- Townhouse rentals Philadelphia
- House rentals Philadelphia
- Lakehouse rentals Philadelphia
- House rentals Baltimore
- Townhouse rentals Baltimore
- Guesthouse rentals Baltimore
- Townhouse rentals Maryland
- House rentals Maryland
- Lakehouse rentals Maryland
- Guesthouse rentals Maryland
- Tiny house rentals Maryland
- Beach house rentals Maryland
- Family-friendly rentals Chestertown
- Rentals with a washer and dryer Chestertown
- Rentals with a patio Chestertown
- Rentals with outdoor seating Chestertown
- Monthly Rentals Chestertown
- House rentals Kent County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes