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Ridgely Holiday Rentals

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5 mi
48 rentals in Ridgely.
The following properties within 20 miles of Ridgely match all your filters:
Blake House Historic Estate with Private Inn, holiday rental in Ridgely
Blake House Historic Estate with Private Inn, holiday rental in Ridgely
Blake House Historic Estate with Private Inn, holiday rental in Ridgely

Blake House Historic Estate with Private Inn

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac, holiday rental in Ridgely
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac, holiday rental in Ridgely
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac, holiday rental in Ridgely

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Abay Palace of Kent Narrows in a King Bed, holiday rental in Ridgely
Abay Palace of Kent Narrows in a King Bed, holiday rental in Ridgely
Abay Palace of Kent Narrows in a King Bed, holiday rental in Ridgely

Abay Palace of Kent Narrows in a King Bed

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Affiliated with FlipKey
Seventh Haven - An oasis of peace and relaxation!, holiday rental in Ridgely
Seventh Haven - An oasis of peace and relaxation!, holiday rental in Ridgely
Seventh Haven - An oasis of peace and relaxation!, holiday rental in Ridgely

Seventh Haven - An oasis of peace and relaxation!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!, holiday rental in Ridgely
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!, holiday rental in Ridgely
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!, holiday rental in Ridgely

Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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EASTON Beautiful APT. 2bed2bathKitchinDining/living room-walk to all places, holiday rental in Ridgely
EASTON Beautiful APT. 2bed2bathKitchinDining/living room-walk to all places, holiday rental in Ridgely
EASTON Beautiful APT. 2bed2bathKitchinDining/living room-walk to all places, holiday rental in Ridgely

EASTON Beautiful APT. 2bed2bathKitchinDining/living room-walk to all places

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Relax and Refresh at Triple Creek Hobby Farm, holiday rental in Ridgely
Relax and Refresh at Triple Creek Hobby Farm, holiday rental in Ridgely
Relax and Refresh at Triple Creek Hobby Farm, holiday rental in Ridgely

Relax and Refresh at Triple Creek Hobby Farm

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Affiliated with FlipKey
Private setting, enjoy nature, kayaking and total relaxation, holiday rental in Ridgely
Private setting, enjoy nature, kayaking and total relaxation, holiday rental in Ridgely
Private setting, enjoy nature, kayaking and total relaxation, holiday rental in Ridgely

Private setting, enjoy nature, kayaking and total relaxation

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Affiliated with FlipKey
KENT ISLAND - Everything The Narrows has to offer you!, holiday rental in Ridgely
KENT ISLAND - Everything The Narrows has to offer you!, holiday rental in Ridgely
KENT ISLAND - Everything The Narrows has to offer you!, holiday rental in Ridgely

KENT ISLAND - Everything The Narrows has to offer you!

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Cozy, unique, historic registered cottage on the Corsica River!, holiday rental in Ridgely
Cozy, unique, historic registered cottage on the Corsica River!, holiday rental in Ridgely
Cozy, unique, historic registered cottage on the Corsica River!, holiday rental in Ridgely

Cozy, unique, historic registered cottage on the Corsica River!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Adorable two-bedroom retreat close to Easton, Denton, Centreville, holiday rental in Ridgely
Adorable two-bedroom retreat close to Easton, Denton, Centreville, holiday rental in Ridgely
Adorable two-bedroom retreat close to Easton, Denton, Centreville, holiday rental in Ridgely

Adorable two-bedroom retreat close to Easton, Denton, Centreville

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Relax on the Eastern Shore of Kent Narrows in a King Bed, holiday rental in Ridgely
Relax on the Eastern Shore of Kent Narrows in a King Bed, holiday rental in Ridgely
Relax on the Eastern Shore of Kent Narrows in a King Bed, holiday rental in Ridgely

Relax on the Eastern Shore of Kent Narrows in a King Bed

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Sudlersville -Very cute Newly renovated 3BR1BA rancher on 4.75 acres, holiday rental in Ridgely
Sudlersville -Very cute Newly renovated 3BR1BA rancher on 4.75 acres, holiday rental in Ridgely
Sudlersville -Very cute Newly renovated 3BR1BA rancher on 4.75 acres, holiday rental in Ridgely

Sudlersville -Very cute Newly renovated 3BR1BA rancher on 4.75 acres

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Amazing River House Waterfront Condo on the Choptank River on 18 Acre Farm, holiday rental in Ridgely
Amazing River House Waterfront Condo on the Choptank River on 18 Acre Farm, holiday rental in Ridgely
Amazing River House Waterfront Condo on the Choptank River on 18 Acre Farm, holiday rental in Ridgely

Amazing River House Waterfront Condo on the Choptank River on 18 Acre Farm

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Belle Blu of Kent Narrows Grasonville, Maryland, holiday rental in Ridgely
Belle Blu of Kent Narrows Grasonville, Maryland, holiday rental in Ridgely
Belle Blu of Kent Narrows Grasonville, Maryland, holiday rental in Ridgely

Belle Blu of Kent Narrows Grasonville, Maryland

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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family friendly nice quiet neighborhood close to most major cities, holiday rental in Ridgely
family friendly nice quiet neighborhood close to most major cities, holiday rental in Ridgely
family friendly nice quiet neighborhood close to most major cities, holiday rental in Ridgely

family friendly nice quiet neighborhood close to most major cities

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Little Creek Hideaway - Privacy and Perfect Family Getaway., holiday rental in Ridgely
Little Creek Hideaway - Privacy and Perfect Family Getaway., holiday rental in Ridgely
Little Creek Hideaway - Privacy and Perfect Family Getaway., holiday rental in Ridgely

Little Creek Hideaway - Privacy and Perfect Family Getaway.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Wye River Cape, holiday rental in Ridgely
Wye River Cape, holiday rental in Ridgely
Wye River Cape, holiday rental in Ridgely

Wye River Cape

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Stunning Waterfront Hideaway on Michener's Choptank River.  Special Rates*, holiday rental in Ridgely
Stunning Waterfront Hideaway on Michener's Choptank River.  Special Rates*, holiday rental in Ridgely
Stunning Waterfront Hideaway on Michener's Choptank River.  Special Rates*, holiday rental in Ridgely

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Grasonville Home w/ Private Pool on the Water, holiday rental in Ridgely
Grasonville Home w/ Private Pool on the Water, holiday rental in Ridgely
Grasonville Home w/ Private Pool on the Water, holiday rental in Ridgely

Grasonville Home w/ Private Pool on the Water

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Gorgeous, waterfront 3-bedroom cottage on Wye River - dog friendly, holiday rental in Ridgely
Gorgeous, waterfront 3-bedroom cottage on Wye River - dog friendly, holiday rental in Ridgely
Gorgeous, waterfront 3-bedroom cottage on Wye River - dog friendly, holiday rental in Ridgely

Gorgeous, waterfront 3-bedroom cottage on Wye River - dog friendly

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Get Away To The Beautiful Wye River, holiday rental in Ridgely
Get Away To The Beautiful Wye River, holiday rental in Ridgely
Get Away To The Beautiful Wye River, holiday rental in Ridgely

Get Away To The Beautiful Wye River

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
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Secluded Waterfront Cottage on 200 acre farm near Queenstown, holiday rental in Ridgely
Secluded Waterfront Cottage on 200 acre farm near Queenstown, holiday rental in Ridgely
Secluded Waterfront Cottage on 200 acre farm near Queenstown, holiday rental in Ridgely

Secluded Waterfront Cottage on 200 acre farm near Queenstown

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Livin' The Dream - There’s Nothing Like a Leeds Creek Sunset!, holiday rental in Ridgely
Livin' The Dream - There’s Nothing Like a Leeds Creek Sunset!, holiday rental in Ridgely
Livin' The Dream - There’s Nothing Like a Leeds Creek Sunset!, holiday rental in Ridgely

Livin' The Dream - There’s Nothing Like a Leeds Creek Sunset!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Ferry Bridge House, holiday rental in Ridgely
Ferry Bridge House, holiday rental in Ridgely
Ferry Bridge House, holiday rental in Ridgely

Ferry Bridge House

Holiday Rental House
3 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
More info
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Affiliated with FlipKey
Private Gated Country Home with Outdoor Pavilion, EV Charger - Dog-Friendly, holiday rental in Ridgely
Private Gated Country Home with Outdoor Pavilion, EV Charger - Dog-Friendly, holiday rental in Ridgely
Private Gated Country Home with Outdoor Pavilion, EV Charger - Dog-Friendly, holiday rental in Ridgely

Private Gated Country Home with Outdoor Pavilion, EV Charger - Dog-Friendly

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Great waterfront house in Grasonville, holiday rental in Ridgely
Great waterfront house in Grasonville, holiday rental in Ridgely
Great waterfront house in Grasonville, holiday rental in Ridgely

Great waterfront house in Grasonville

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Lansdowne Manor, holiday rental in Ridgely
Lansdowne Manor, holiday rental in Ridgely
Lansdowne Manor, holiday rental in Ridgely

Lansdowne Manor

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Windward Cove - Close to Annapolis, Waterfront, Kayaks, Bikes, Game Room, holiday rental in Ridgely
Windward Cove - Close to Annapolis, Waterfront, Kayaks, Bikes, Game Room, holiday rental in Ridgely
Windward Cove - Close to Annapolis, Waterfront, Kayaks, Bikes, Game Room, holiday rental in Ridgely

Windward Cove - Close to Annapolis, Waterfront, Kayaks, Bikes, Game Room

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Leeds Landing | A Perfect Single-Story Waterfront Retreat!, holiday rental in Ridgely
Leeds Landing | A Perfect Single-Story Waterfront Retreat!, holiday rental in Ridgely
Leeds Landing | A Perfect Single-Story Waterfront Retreat!, holiday rental in Ridgely

Leeds Landing | A Perfect Single-Story Waterfront Retreat!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Stylish Home on the Choptank River (with Tidal Beach), holiday rental in Ridgely
Stylish Home on the Choptank River (with Tidal Beach), holiday rental in Ridgely
Stylish Home on the Choptank River (with Tidal Beach), holiday rental in Ridgely

Stylish Home on the Choptank River (with Tidal Beach)

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Wye Topia - Ideal felicity and perfection!, holiday rental in Ridgely
Wye Topia - Ideal felicity and perfection!, holiday rental in Ridgely
Wye Topia - Ideal felicity and perfection!, holiday rental in Ridgely

Wye Topia - Ideal felicity and perfection!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Turnbridge Manor, holiday rental in Ridgely
Turnbridge Manor, holiday rental in Ridgely
Turnbridge Manor, holiday rental in Ridgely

Turnbridge Manor

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Eastern Shore Oasis!, holiday rental in Ridgely
Eastern Shore Oasis!, holiday rental in Ridgely
Eastern Shore Oasis!, holiday rental in Ridgely

Eastern Shore Oasis!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Bay Breeze - The Perfect Escape!, holiday rental in Ridgely
Bay Breeze - The Perfect Escape!, holiday rental in Ridgely
Bay Breeze - The Perfect Escape!, holiday rental in Ridgely

Bay Breeze - The Perfect Escape!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Creek Cottage at Reed Creek Farm - Idyllic, Pet-Friendly Waterfront Farm - Pool,, holiday rental in Ridgely
Creek Cottage at Reed Creek Farm - Idyllic, Pet-Friendly Waterfront Farm - Pool,, holiday rental in Ridgely
Creek Cottage at Reed Creek Farm - Idyllic, Pet-Friendly Waterfront Farm - Pool,, holiday rental in Ridgely

Creek Cottage at Reed Creek Farm - Idyllic, Pet-Friendly Waterfront Farm - Pool,

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Tuckaway Cove Private, relaxing waterfront property; close to everything!, holiday rental in Ridgely
Tuckaway Cove Private, relaxing waterfront property; close to everything!, holiday rental in Ridgely
Tuckaway Cove Private, relaxing waterfront property; close to everything!, holiday rental in Ridgely

Tuckaway Cove Private, relaxing waterfront property; close to everything!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sky View | Vacation With No Limits!, holiday rental in Ridgely
Sky View | Vacation With No Limits!, holiday rental in Ridgely
Sky View | Vacation With No Limits!, holiday rental in Ridgely

Sky View | Vacation With No Limits!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront 4 BR home with private pier and boat dock, holiday rental in Ridgely
Waterfront 4 BR home with private pier and boat dock, holiday rental in Ridgely
Waterfront 4 BR home with private pier and boat dock, holiday rental in Ridgely

Waterfront 4 BR home with private pier and boat dock

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Mill Creek - Cool Contemporary Waterfront - Pool, Grill, Dock!, holiday rental in Ridgely
Mill Creek - Cool Contemporary Waterfront - Pool, Grill, Dock!, holiday rental in Ridgely
Mill Creek - Cool Contemporary Waterfront - Pool, Grill, Dock!, holiday rental in Ridgely

Mill Creek - Cool Contemporary Waterfront - Pool, Grill, Dock!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Quailsar Farm | Toto, There’s No Place Like This Vacation Home!, holiday rental in Ridgely
Quailsar Farm | Toto, There’s No Place Like This Vacation Home!, holiday rental in Ridgely
Quailsar Farm | Toto, There’s No Place Like This Vacation Home!, holiday rental in Ridgely

Quailsar Farm | Toto, There’s No Place Like This Vacation Home!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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The Colonial Farmhouse, holiday rental in Ridgely
The Colonial Farmhouse, holiday rental in Ridgely
The Colonial Farmhouse, holiday rental in Ridgely

The Colonial Farmhouse

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Private, Luxury Family Retreat - Corsica River on Maryland's Eastern Shore, holiday rental in Ridgely
Private, Luxury Family Retreat - Corsica River on Maryland's Eastern Shore, holiday rental in Ridgely
Private, Luxury Family Retreat - Corsica River on Maryland's Eastern Shore, holiday rental in Ridgely

Private, Luxury Family Retreat - Corsica River on Maryland's Eastern Shore

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront family resort Lodge with private pier, game room and bar, holiday rental in Ridgely
Waterfront family resort Lodge with private pier, game room and bar, holiday rental in Ridgely
Waterfront family resort Lodge with private pier, game room and bar, holiday rental in Ridgely

Waterfront family resort Lodge with private pier, game room and bar

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Waterfront family resort Lodge with private pier, game room and bar, holiday rental in Ridgely
Waterfront family resort Lodge with private pier, game room and bar, holiday rental in Ridgely
Waterfront family resort Lodge with private pier, game room and bar, holiday rental in Ridgely

Waterfront family resort Lodge with private pier, game room and bar

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
More info
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Affiliated with FlipKey
Whitehall Acres - Lovely and serene-the perfect spot to nurture your soul!, holiday rental in Ridgely
Whitehall Acres - Lovely and serene-the perfect spot to nurture your soul!, holiday rental in Ridgely
Whitehall Acres - Lovely and serene-the perfect spot to nurture your soul!, holiday rental in Ridgely

Whitehall Acres - Lovely and serene-the perfect spot to nurture your soul!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront oasis, tranquil masterpiece for relaxing and recreating, holiday rental in Ridgely
Waterfront oasis, tranquil masterpiece for relaxing and recreating, holiday rental in Ridgely
Waterfront oasis, tranquil masterpiece for relaxing and recreating, holiday rental in Ridgely

Waterfront oasis, tranquil masterpiece for relaxing and recreating

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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Sprawling Waterfront Home, Dock & In-Home Theatre, holiday rental in Ridgely
Sprawling Waterfront Home, Dock & In-Home Theatre, holiday rental in Ridgely
Sprawling Waterfront Home, Dock & In-Home Theatre, holiday rental in Ridgely

Sprawling Waterfront Home, Dock & In-Home Theatre

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Frequently Asked Questions about Ridgely