Holiday Rentals in Chester
Revenue impacts this sort order. Learn more
Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
50 rentals in Chester.
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Bentons Pleasure- Cox Creek, Pier and Sunsets!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Waterfront home with private pier is A Shore Thing
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
DOLCE VIDA -KENT ISLAND HOME WITH POOL AND OCEAN VIEW-sleeps 10-12-PETS ALLOWED
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Kent Island - Gorgeous Waterfront Home
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Kent Island Time - Waterfront
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Renovated Rancher on Kent Island near Chesapeake Bay Bridge
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
The following properties within 32 kms of Chester match all your filters:
240' Private Beachfront *Kent Island Love Point - Great for Large Groups
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 26
Match: Sleeps
More info
Check-in
Check-out
Private beach spot
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
ADULT ONLY! Magnificent Waterfront Cottage on 5 Acres
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Serene Waterfront Apartment on Kent Island
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Cape Cod Bed and Bath
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Cass-Away Luxury Houseboat
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Sunsets and 4 King Bedrooms - Sunny Isle of Kent Across the Water from Annapolis
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Love Point Waterfront
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Chesapeake Bay Waterfront ARTectural Home
Holiday Rental House
3 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Circa 1700 Chesapeake Colonial home on the National Register.
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Relax on the Eastern Shore of Kent Narrows in a King Bed
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Blue Bay Haven - Stunning Newly Renovated Waterfront Home near Annapolis!
Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
Serene Waterfront Apartment on Kent Island
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Abay Palace of Kent Narrows in a King Bed
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Come explore Maryland's Eastern Shore. Near Annapolis, Wash. D.C. and Baltimore
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Waterfront property on 3/4 acres with private beach, pool, hot tub, and pier.
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Private pier at Waterfront Kent Island home with Hot Tub (Open!)
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Grasonville Home w/ Private Pool on the Water
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Bay Breeze - The Perfect Escape!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
New! Stylish downtown home w/awesome outdoor area!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Waterfront 4 BR home with private pier and boat dock
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Luxe Home-Bay Views! Near Annapolis! w/ Fireplace! Game Room!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Chester River Waterfront Cottage (Love Point Bay)
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Love Point Luxury Waterfront
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Lighthouse Haven of Kent Island
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Beautiful Chesapeake Bay Views -pet friendly
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Fish to the Left of Me, Geese to the right, Stuck in the middle w/ Goats
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Great waterfront house in Grasonville
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Kent Island waterfront spectacular Chesapeake Bay view
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Fabulous Colonial in Cloverfields on Kent Island! Beautifully Furnished 4
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Cass-N-Reel Luxury Houseboat
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Kent Island Luxary Home W/ Pool and walking distance from the beach
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Lovely Chesapeake bay home, on the bay with beautiful sunsets
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Sprawling Waterfront Home, Dock & In-Home Theatre
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Belle Blu of Kent Narrows Grasonville, Maryland
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Apartment with Lounge Stevensville, MD
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Showing results 1-50 of 50
Frequently Asked Questions about Chester
- Yes, here are some popular holiday rentals in Chester that have a pool:
- DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12
- Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)
- Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!
- Yes, here are some popular holiday rentals in Chester that have internet access:
- Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)
- Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!
- Kent Island Time - Waterfront
- Some of the most popular kid friendly rentals in Chester are:
- Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)
- Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!
- Kent Island Time - Waterfront