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Chester Holiday Rentals

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50 rentals in Chester.
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Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets), holiday rental in Chester

Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

4 bedrooms
2 bathrooms
Sleeps 8
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Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!, holiday rental in Chester

Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Secluded Waterfront Cottage on 200 acre farm near Queenstown, holiday rental in Chester

Secluded Waterfront Cottage on 200 acre farm near Queenstown

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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240' Private Beachfront *Kent Island Love Point-Reunions/Rehearsal Dinners, holiday rental in Chester

240' Private Beachfront *Kent Island Love Point-Reunions/Rehearsal Dinners

5 bedrooms
5 bathrooms
Sleeps 26
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Private Waterfront Retreat, holiday rental in Chester

Private Waterfront Retreat

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Stunning Views of the Bay - Waterfront, holiday rental in Chester

Stunning Views of the Bay - Waterfront

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Enhanced Cleaning & Disinfecting. Private Beach Volleyball Court. Walk to Beach., holiday rental in Chester

Enhanced Cleaning & Disinfecting. Private Beach Volleyball Court. Walk to Beach.

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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ADULT ONLY! Magnificent Waterfront Cottage on 5 Acres, holiday rental in Chester

ADULT ONLY! Magnificent Waterfront Cottage on 5 Acres

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Magical Memories - Annapolis Chesapeake Bay Waterfront Home w/Pool., holiday rental in Chester

Magical Memories - Annapolis Chesapeake Bay Waterfront Home w/Pool.

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, holiday rental in Chester

THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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The Winehouse at Love Point Vineyards and Winery, holiday rental in Chester

The Winehouse at Love Point Vineyards and Winery

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Charming 3 Bedroom 3 Bath Beach Front Property, holiday rental in Chester

Charming 3 Bedroom 3 Bath Beach Front Property

3 bedrooms
3 bathrooms
Sleeps 12
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Walk everywhere . . .just minutes to historic Annapolis,  Updated., holiday rental in Chester

Walk everywhere . . .just minutes to historic Annapolis, Updated.

2 bedrooms
2 bathrooms
Sleeps 4
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Views! Charming Renovated Beachfront House in Bay Ridge Annapolis. 10 min dwntwn, holiday rental in Chester

Views! Charming Renovated Beachfront House in Bay Ridge Annapolis. 10 min dwntwn

4 bedrooms
3 bathrooms
Sleeps 10
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Welcome Aboard the Kathleen Marie!, holiday rental in Chester

Welcome Aboard the Kathleen Marie!

2 bedrooms
2 bathrooms
Sleeps 4
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Historic beach Cottage, holiday rental in Chester

Historic beach Cottage

3 bedrooms
2 bathrooms
Sleeps 8
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Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, holiday rental in Chester

Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Cottage by the Beach, holiday rental in Chester

Cozy Cottage by the Beach

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Luxurious Waterfront Kent Island Home 30 miles from Annapolis, holiday rental in Chester

Luxurious Waterfront Kent Island Home 30 miles from Annapolis

4 bedrooms
5 bathrooms
Sleeps 7
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Legislative Session 2021 is Available., holiday rental in Chester

Legislative Session 2021 is Available.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Holiday on the Bay, Kent Island Beach House, holiday rental in Chester

Holiday on the Bay, Kent Island Beach House

4 bedrooms
2 bathrooms
Sleeps 10
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Cape Cod Bed and Bath, holiday rental in Chester

Cape Cod Bed and Bath

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Enhanced Cleaning and Disinfecting. Million$ Chesapeake Bay Sunsets by the Bay., holiday rental in Chester

Enhanced Cleaning and Disinfecting. Million$ Chesapeake Bay Sunsets by the Bay.

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Serene Waterfront Cottage with dock and gorgeous views., holiday rental in Chester

Serene Waterfront Cottage with dock and gorgeous views.

1 bedroom
2 bathrooms
Sleeps 7
Match: Sleeps
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Waterside with it All! Private Pier, Hot Tub and Pool., holiday rental in Chester

Waterside with it All! Private Pier, Hot Tub and Pool.

6 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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0198 Days Landing. Your Chesapeake Family Getaway! Lake, Pool, Hot Tub, Dock., holiday rental in Chester

0198 Days Landing. Your Chesapeake Family Getaway! Lake, Pool, Hot Tub, Dock.

6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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Overton Farm Cottage, holiday rental in Chester

Overton Farm Cottage

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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0025 Bella Chateau. SPECIAL Commissioning Week 2021 Discount! Ask!, holiday rental in Chester

0025 Bella Chateau. SPECIAL Commissioning Week 2021 Discount! Ask!

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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KI Golf House-A PAR for the Course & Mile to Beach, holiday rental in Chester

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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Upscale home in Eastport / Annapolis, holiday rental in Chester

Upscale home in Eastport / Annapolis

4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Retreat for Four in Eastport, Steps away from Restaurant Row & Downtown, holiday rental in Chester

Retreat for Four in Eastport, Steps away from Restaurant Row & Downtown

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beatiful Waterfront Home with Large Deck, Pool and Spa close to Bay Bridge, holiday rental in Chester

Beatiful Waterfront Home with Large Deck, Pool and Spa close to Bay Bridge

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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KENT ISLAND-OCEAN VIEW Home for rent  -4 bedrooms EASTERN SHORE sleeps 10-12, holiday rental in Chester

KENT ISLAND-OCEAN VIEW Home for rent -4 bedrooms EASTERN SHORE sleeps 10-12

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, holiday rental in Chester

BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Annapolis Waterfront home with incredible views, holiday rental in Chester

Annapolis Waterfront home with incredible views

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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UNFORGETTABLE FAMILY GETAWAY. This fully renovated home has it all.  3 sides of, holiday rental in Chester

UNFORGETTABLE FAMILY GETAWAY. This fully renovated home has it all. 3 sides of

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Clean & Spacious, holiday rental in Chester

Clean & Spacious

4 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina, holiday rental in Chester

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

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Serene Waterfront Apartment on Kent Island, holiday rental in Chester

Serene Waterfront Apartment on Kent Island

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Annapolis House w/ Patio in Bay Ridge Maryland!, holiday rental in Chester

Annapolis House w/ Patio in Bay Ridge Maryland!

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Annapolis Home w/ Deck & Whitehall Bay Access, holiday rental in Chester

Annapolis Home w/ Deck & Whitehall Bay Access

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Annapolis Waterview home, holiday rental in Chester

Charming Annapolis Waterview home

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Chesapeake Bay Waterfront ARTectural Home, holiday rental in Chester

Chesapeake Bay Waterfront ARTectural Home

3 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Bayfront Beach house overlooks Chesapeake Bay and Thomas Point Light House sleep, holiday rental in Chester

Bayfront Beach house overlooks Chesapeake Bay and Thomas Point Light House sleep

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Fully Furnished 4 Bedroom/3 Bathroom Single Family Home in Annapolis: This fully, holiday rental in Chester

Fully Furnished 4 Bedroom/3 Bathroom Single Family Home in Annapolis: This fully

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Annapolis Home: Fire Pit & Fishing Pier, holiday rental in Chester

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront Chesapeake Cottage in Oyster Bay - Dock, holiday rental in Chester

Waterfront Chesapeake Cottage in Oyster Bay - Dock

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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3BR 1BA Private Beach / Pool / Boat Launch / Pier / Golf Cart and much more!, holiday rental in Chester

3BR 1BA Private Beach / Pool / Boat Launch / Pier / Golf Cart and much more!

3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Newly Listed - Renovated Historical House in Eastport neighborhood of Annapolis, holiday rental in Chester

Newly Listed - Renovated Historical House in Eastport neighborhood of Annapolis

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Newly Listed - Charming Farmhouse in the heart of Stevensville Historic Village, holiday rental in Chester

Newly Listed - Charming Farmhouse in the heart of Stevensville Historic Village

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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