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Preston Vacation Rentals

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Bedrooms

Bathrooms

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Distance from

5 mi
50 rentals in Preston.
Stylish Home on the Choptank River (with Tidal Beach), vacation rental in Preston
Stylish Home on the Choptank River (with Tidal Beach), vacation rental in Preston
Stylish Home on the Choptank River (with Tidal Beach), vacation rental in Preston

Stylish Home on the Choptank River (with Tidal Beach)

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The following properties within 20 miles of Preston match all your filters:
A little slice of heaven on the Choptank River, vacation rental in Preston
A little slice of heaven on the Choptank River, vacation rental in Preston
A little slice of heaven on the Choptank River, vacation rental in Preston

A little slice of heaven on the Choptank River

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels / Easton, vacation rental in Preston
Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels / Easton, vacation rental in Preston
Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels / Easton, vacation rental in Preston

Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels / Easton

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Cottage on Cabin Creek, vacation rental in Preston
Cottage on Cabin Creek, vacation rental in Preston
Cottage on Cabin Creek, vacation rental in Preston

Cottage on Cabin Creek

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Seventh Haven - An oasis of peace and relaxation!, vacation rental in Preston
Seventh Haven - An oasis of peace and relaxation!, vacation rental in Preston
Seventh Haven - An oasis of peace and relaxation!, vacation rental in Preston

Seventh Haven - An oasis of peace and relaxation!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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EASTON Beautiful APT. 2bed2bathKitchinDining/living room-walk to all places, vacation rental in Preston
EASTON Beautiful APT. 2bed2bathKitchinDining/living room-walk to all places, vacation rental in Preston
EASTON Beautiful APT. 2bed2bathKitchinDining/living room-walk to all places, vacation rental in Preston

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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5 bedroom Bed and Breakfast on the Choptank River, vacation rental in Preston
5 bedroom Bed and Breakfast on the Choptank River, vacation rental in Preston
5 bedroom Bed and Breakfast on the Choptank River, vacation rental in Preston

5 bedroom Bed and Breakfast on the Choptank River

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private setting, enjoy nature, kayaking and total relaxation, vacation rental in Preston
Private setting, enjoy nature, kayaking and total relaxation, vacation rental in Preston
Private setting, enjoy nature, kayaking and total relaxation, vacation rental in Preston

Private setting, enjoy nature, kayaking and total relaxation

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Affiliated with FlipKey
The B&B of Anchorage - Skipjack, vacation rental in Preston
The B&B of Anchorage - Skipjack, vacation rental in Preston
The B&B of Anchorage - Skipjack, vacation rental in Preston

The B&B of Anchorage - Skipjack

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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The Anchorage B&B - The Bounty, vacation rental in Preston
The Anchorage B&B - The Bounty, vacation rental in Preston
The Anchorage B&B - The Bounty, vacation rental in Preston

The Anchorage B&B - The Bounty

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Private Waterfront Cottage on Bolingbroke Creek, vacation rental in Preston
Private Waterfront Cottage on Bolingbroke Creek, vacation rental in Preston
Private Waterfront Cottage on Bolingbroke Creek, vacation rental in Preston

Private Waterfront Cottage on Bolingbroke Creek

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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High Water Guest House, vacation rental in Preston
High Water Guest House, vacation rental in Preston
High Water Guest House, vacation rental in Preston

High Water Guest House

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Relax or Play on the Choptank River!, vacation rental in Preston
Relax or Play on the Choptank River!, vacation rental in Preston
Relax or Play on the Choptank River!, vacation rental in Preston

Relax or Play on the Choptank River!

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Cheerful three-bedroom Cottage, vacation rental in Preston
Cheerful three-bedroom Cottage, vacation rental in Preston
Cheerful three-bedroom Cottage, vacation rental in Preston

Cheerful three-bedroom Cottage

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Charming Cottage on Bolingbroke Creek, vacation rental in Preston
Charming Cottage on Bolingbroke Creek, vacation rental in Preston
Charming Cottage on Bolingbroke Creek, vacation rental in Preston

Charming Cottage on Bolingbroke Creek

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Little Creek Hideaway - Privacy and Perfect Family Getaway., vacation rental in Preston
Little Creek Hideaway - Privacy and Perfect Family Getaway., vacation rental in Preston
Little Creek Hideaway - Privacy and Perfect Family Getaway., vacation rental in Preston

Little Creek Hideaway - Privacy and Perfect Family Getaway.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Cambridge Home w/ Private Dock ~ 4 Mi to Dtwn, vacation rental in Preston
Cambridge Home w/ Private Dock ~ 4 Mi to Dtwn, vacation rental in Preston
Cambridge Home w/ Private Dock ~ 4 Mi to Dtwn, vacation rental in Preston

Cambridge Home w/ Private Dock ~ 4 Mi to Dtwn

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Waterfront Home on the Choptank River in Cambridge MD 3 bed room 2 bath and pool, vacation rental in Preston
Waterfront Home on the Choptank River in Cambridge MD 3 bed room 2 bath and pool, vacation rental in Preston
Waterfront Home on the Choptank River in Cambridge MD 3 bed room 2 bath and pool, vacation rental in Preston

Waterfront Home on the Choptank River in Cambridge MD 3 bed room 2 bath and pool

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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New listing! Riverside Retreat on the Choptank River, vacation rental in Preston
New listing! Riverside Retreat on the Choptank River, vacation rental in Preston
New listing! Riverside Retreat on the Choptank River, vacation rental in Preston

New listing! Riverside Retreat on the Choptank River

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels, vacation rental in Preston
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels, vacation rental in Preston
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels, vacation rental in Preston

A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Cozy Home in Historic West End Perfect for Ironman, vacation rental in Preston
Cozy Home in Historic West End Perfect for Ironman, vacation rental in Preston
Cozy Home in Historic West End Perfect for Ironman, vacation rental in Preston

Cozy Home in Historic West End Perfect for Ironman

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful Colonial Home on the Choptank River, vacation rental in Preston
Beautiful Colonial Home on the Choptank River, vacation rental in Preston
Beautiful Colonial Home on the Choptank River, vacation rental in Preston

Beautiful Colonial Home on the Choptank River

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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American Pride at Sunset Point, vacation rental in Preston
American Pride at Sunset Point, vacation rental in Preston
American Pride at Sunset Point, vacation rental in Preston

American Pride at Sunset Point

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Attractive Waterfront Home over looking Choptank River with modern conviences!, vacation rental in Preston
Attractive Waterfront Home over looking Choptank River with modern conviences!, vacation rental in Preston
Attractive Waterfront Home over looking Choptank River with modern conviences!, vacation rental in Preston

Attractive Waterfront Home over looking Choptank River with modern conviences!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Judith's Garden - Quaint Waterfront Home Near Oxford - Pool, Grill, Kayaks!, vacation rental in Preston
Judith's Garden - Quaint Waterfront Home Near Oxford - Pool, Grill, Kayaks!, vacation rental in Preston
Judith's Garden - Quaint Waterfront Home Near Oxford - Pool, Grill, Kayaks!, vacation rental in Preston

Judith's Garden - Quaint Waterfront Home Near Oxford - Pool, Grill, Kayaks!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Waterfront Haven in Cambridge, Md - sleeps 10, 4 bedrooms, vacation rental in Preston
Waterfront Haven in Cambridge, Md - sleeps 10, 4 bedrooms, vacation rental in Preston
Waterfront Haven in Cambridge, Md - sleeps 10, 4 bedrooms, vacation rental in Preston

Waterfront Haven in Cambridge, Md - sleeps 10, 4 bedrooms

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Tranquil Easton Waterfront Property (Pool, Tennis court, Hot Tub, Fireplace), vacation rental in Preston
Tranquil Easton Waterfront Property (Pool, Tennis court, Hot Tub, Fireplace), vacation rental in Preston
Tranquil Easton Waterfront Property (Pool, Tennis court, Hot Tub, Fireplace), vacation rental in Preston

Tranquil Easton Waterfront Property (Pool, Tennis court, Hot Tub, Fireplace)

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Private Gated Country Home with Outdoor Pavilion, EV Charger - Dog-Friendly, vacation rental in Preston
Private Gated Country Home with Outdoor Pavilion, EV Charger - Dog-Friendly, vacation rental in Preston
Private Gated Country Home with Outdoor Pavilion, EV Charger - Dog-Friendly, vacation rental in Preston

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

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Spend fall at the Sunsets Edge., vacation rental in Preston
Spend fall at the Sunsets Edge., vacation rental in Preston
Spend fall at the Sunsets Edge., vacation rental in Preston

Spend fall at the Sunsets Edge.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Waterside 4-Bedroom Chesapeake Styled Townhome, vacation rental in Preston
Waterside 4-Bedroom Chesapeake Styled Townhome, vacation rental in Preston
Waterside 4-Bedroom Chesapeake Styled Townhome, vacation rental in Preston

Waterside 4-Bedroom Chesapeake Styled Townhome

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Tranquil Easton Waterfront Property, vacation rental in Preston
Tranquil Easton Waterfront Property, vacation rental in Preston
Tranquil Easton Waterfront Property, vacation rental in Preston

Tranquil Easton Waterfront Property

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Affiliated with FlipKey
Waterfront Retreat < 4 Mi to Dtwn Cambridge!, vacation rental in Preston
Waterfront Retreat < 4 Mi to Dtwn Cambridge!, vacation rental in Preston
Waterfront Retreat < 4 Mi to Dtwn Cambridge!, vacation rental in Preston

Waterfront Retreat < 4 Mi to Dtwn Cambridge!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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Large Luxury Townhouse with Elevator adjacent to the Chesapeake Hyatt, vacation rental in Preston
Large Luxury Townhouse with Elevator adjacent to the Chesapeake Hyatt, vacation rental in Preston
Large Luxury Townhouse with Elevator adjacent to the Chesapeake Hyatt, vacation rental in Preston

Large Luxury Townhouse with Elevator adjacent to the Chesapeake Hyatt

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Oak Hill at Snug Harbor, vacation rental in Preston
Oak Hill at Snug Harbor, vacation rental in Preston
Oak Hill at Snug Harbor, vacation rental in Preston

Oak Hill at Snug Harbor

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Blue Gates - Elegantly Appointed Estate with Fantastic Outdoor Areas, vacation rental in Preston
Blue Gates - Elegantly Appointed Estate with Fantastic Outdoor Areas, vacation rental in Preston
Blue Gates - Elegantly Appointed Estate with Fantastic Outdoor Areas, vacation rental in Preston

Blue Gates - Elegantly Appointed Estate with Fantastic Outdoor Areas

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Waterfront Vintage Eastern Shore Retreat, vacation rental in Preston
Waterfront Vintage Eastern Shore Retreat, vacation rental in Preston
Waterfront Vintage Eastern Shore Retreat, vacation rental in Preston

Waterfront Vintage Eastern Shore Retreat

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River, vacation rental in Preston
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River, vacation rental in Preston
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River, vacation rental in Preston

Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Delightful Cambridge Home on Choptank River!, vacation rental in Preston
Delightful Cambridge Home on Choptank River!, vacation rental in Preston
Delightful Cambridge Home on Choptank River!, vacation rental in Preston

Delightful Cambridge Home on Choptank River!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Turnbridge Manor, vacation rental in Preston
Turnbridge Manor, vacation rental in Preston
Turnbridge Manor, vacation rental in Preston

Turnbridge Manor

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Eastern Shore Oasis!, vacation rental in Preston
Eastern Shore Oasis!, vacation rental in Preston
Eastern Shore Oasis!, vacation rental in Preston

Eastern Shore Oasis!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Warwick River Retreat- Waterfront, Private Saltwater Pool & Dock, Sleeps 8, vacation rental in Preston
Warwick River Retreat- Waterfront, Private Saltwater Pool & Dock, Sleeps 8, vacation rental in Preston
Warwick River Retreat- Waterfront, Private Saltwater Pool & Dock, Sleeps 8, vacation rental in Preston

Warwick River Retreat- Waterfront, Private Saltwater Pool & Dock, Sleeps 8

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Pristine 5 Acre Home/Pool/Pool House, vacation rental in Preston
Pristine 5 Acre Home/Pool/Pool House, vacation rental in Preston
Pristine 5 Acre Home/Pool/Pool House, vacation rental in Preston

Pristine 5 Acre Home/Pool/Pool House

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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Tuckaway Cove Private, relaxing waterfront property; close to everything!, vacation rental in Preston
Tuckaway Cove Private, relaxing waterfront property; close to everything!, vacation rental in Preston
Tuckaway Cove Private, relaxing waterfront property; close to everything!, vacation rental in Preston

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Holly Harbor Court - Waterfront Perfection!, vacation rental in Preston
Holly Harbor Court - Waterfront Perfection!, vacation rental in Preston
Holly Harbor Court - Waterfront Perfection!, vacation rental in Preston

Holly Harbor Court - Waterfront Perfection!

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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Magnificent Historic Home by Water is Ready!, vacation rental in Preston
Magnificent Historic Home by Water is Ready!, vacation rental in Preston
Magnificent Historic Home by Water is Ready!, vacation rental in Preston

Magnificent Historic Home by Water is Ready!

Rental Home
5 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
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Quailsar Farm | Toto, There’s No Place Like This Vacation Home!, vacation rental in Preston
Quailsar Farm | Toto, There’s No Place Like This Vacation Home!, vacation rental in Preston
Quailsar Farm | Toto, There’s No Place Like This Vacation Home!, vacation rental in Preston

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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Competitive Rates! New Luxury Listing Surrounded By Water! Central Location., vacation rental in Preston
Competitive Rates! New Luxury Listing Surrounded By Water! Central Location., vacation rental in Preston
Competitive Rates! New Luxury Listing Surrounded By Water! Central Location., vacation rental in Preston

Competitive Rates! New Luxury Listing Surrounded By Water! Central Location.

Rental Home
5 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
More info
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Beautiful historic waterfront home on 30+ acres, vacation rental in Preston
Beautiful historic waterfront home on 30+ acres, vacation rental in Preston
Beautiful historic waterfront home on 30+ acres, vacation rental in Preston

Beautiful historic waterfront home on 30+ acres

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
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Belle Aire Landing - Choptank River Family Compound, vacation rental in Preston
Belle Aire Landing - Choptank River Family Compound, vacation rental in Preston
Belle Aire Landing - Choptank River Family Compound, vacation rental in Preston

Belle Aire Landing - Choptank River Family Compound

Rental Home
9 bedrooms
6 bathrooms
Sleeps 22
Match: Sleeps
More info
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Cozy & Spacious, The Calway Inn, vacation rental in Preston
Cozy & Spacious, The Calway Inn, vacation rental in Preston
Cozy & Spacious, The Calway Inn, vacation rental in Preston

Cozy & Spacious, The Calway Inn

Rental Home
11 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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