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Rose Haven Vacation Rentals

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50 rentals in Rose Haven.
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Play & relax at the Bungalow! Easily walk to beautiful Herrington Harbour South!, vacation rental in Rose Haven
Play & relax at the Bungalow! Easily walk to beautiful Herrington Harbour South!, vacation rental in Rose Haven
Play & relax at the Bungalow! Easily walk to beautiful Herrington Harbour South!, vacation rental in Rose Haven

Play & relax at the Bungalow! Easily walk to beautiful Herrington Harbour South!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, vacation rental in Rose Haven
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, vacation rental in Rose Haven
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, vacation rental in Rose Haven

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Rental Home
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Spacious house with great deck close to boardwalk, shops, and restaurants.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Chesapeake Bay Cottage, vacation rental in Rose Haven
Chesapeake Bay Cottage, vacation rental in Rose Haven
Chesapeake Bay Cottage, vacation rental in Rose Haven

Chesapeake Bay Cottage

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private Waterfront Home w/ Pier and 2+ Acres!, vacation rental in Rose Haven
Private Waterfront Home w/ Pier and 2+ Acres!, vacation rental in Rose Haven
Private Waterfront Home w/ Pier and 2+ Acres!, vacation rental in Rose Haven

Private Waterfront Home w/ Pier and 2+ Acres!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Million Dollar View on the Chesapeake Bay, vacation rental in Rose Haven
Million Dollar View on the Chesapeake Bay, vacation rental in Rose Haven
Million Dollar View on the Chesapeake Bay, vacation rental in Rose Haven

Million Dollar View on the Chesapeake Bay

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Fully remodel 2 bedroom country cottage., vacation rental in Rose Haven
Fully remodel 2 bedroom country cottage., vacation rental in Rose Haven
Fully remodel 2 bedroom country cottage., vacation rental in Rose Haven

Fully remodel 2 bedroom country cottage.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Looking to get away this September? Gorgeous waterfront property awaits., vacation rental in Rose Haven
Looking to get away this September? Gorgeous waterfront property awaits., vacation rental in Rose Haven
Looking to get away this September? Gorgeous waterfront property awaits., vacation rental in Rose Haven

Looking to get away this September? Gorgeous waterfront property awaits.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming 3 Bedroom 3 Bath Beach Front Property, vacation rental in Rose Haven
Charming 3 Bedroom 3 Bath Beach Front Property, vacation rental in Rose Haven
Charming 3 Bedroom 3 Bath Beach Front Property, vacation rental in Rose Haven

Charming 3 Bedroom 3 Bath Beach Front Property

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Perfect Relaxing, Fun, Dog-Friendly Get-Away for Families, Groups or Couples

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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BeachWalk Cottage  - Charm by the Chesapeake Bay., vacation rental in Rose Haven
BeachWalk Cottage  - Charm by the Chesapeake Bay., vacation rental in Rose Haven
BeachWalk Cottage  - Charm by the Chesapeake Bay., vacation rental in Rose Haven

BeachWalk Cottage - Charm by the Chesapeake Bay.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Simplicity Cottage - Renovated Waterman's Home Circa 1920, Relax in the Hammock!, vacation rental in Rose Haven
Simplicity Cottage - Renovated Waterman's Home Circa 1920, Relax in the Hammock!, vacation rental in Rose Haven
Simplicity Cottage - Renovated Waterman's Home Circa 1920, Relax in the Hammock!, vacation rental in Rose Haven

Simplicity Cottage - Renovated Waterman's Home Circa 1920, Relax in the Hammock!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Spacious Luxury 6 BR Home, Sleeps 20, Private Pool, In Nature, Convenient to DC, vacation rental in Rose Haven
Spacious Luxury 6 BR Home, Sleeps 20, Private Pool, In Nature, Convenient to DC, vacation rental in Rose Haven
Spacious Luxury 6 BR Home, Sleeps 20, Private Pool, In Nature, Convenient to DC, vacation rental in Rose Haven

Spacious Luxury 6 BR Home, Sleeps 20, Private Pool, In Nature, Convenient to DC

Rental Home
6 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
More info
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Relax in Tilghman Island, vacation rental in Rose Haven
Relax in Tilghman Island, vacation rental in Rose Haven
Relax in Tilghman Island, vacation rental in Rose Haven

Relax in Tilghman Island

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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WATERFRONT - DRIFTWOOD LODGE, vacation rental in Rose Haven
WATERFRONT - DRIFTWOOD LODGE, vacation rental in Rose Haven
WATERFRONT - DRIFTWOOD LODGE, vacation rental in Rose Haven

WATERFRONT - DRIFTWOOD LODGE

Rental Home
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Rockhold Creek Cottage, Water Front, Vacation Home, Docks, vacation rental in Rose Haven
Rockhold Creek Cottage, Water Front, Vacation Home, Docks, vacation rental in Rose Haven
Rockhold Creek Cottage, Water Front, Vacation Home, Docks, vacation rental in Rose Haven

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely 3 bedroom 2 bath fully renovated cottage Sleeps 6, vacation rental in Rose Haven
Lovely 3 bedroom 2 bath fully renovated cottage Sleeps 6, vacation rental in Rose Haven
Lovely 3 bedroom 2 bath fully renovated cottage Sleeps 6, vacation rental in Rose Haven

Lovely 3 bedroom 2 bath fully renovated cottage Sleeps 6

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Tilghman Island Cottage - Across from Marina and Knapps Narrows, vacation rental in Rose Haven
Tilghman Island Cottage - Across from Marina and Knapps Narrows, vacation rental in Rose Haven
Tilghman Island Cottage - Across from Marina and Knapps Narrows, vacation rental in Rose Haven

Tilghman Island Cottage - Across from Marina and Knapps Narrows

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Stunning Cottage Newly Renovated 2 Bed 2 Bath Sleeps 6 with an AMAZING Yard, vacation rental in Rose Haven
Stunning Cottage Newly Renovated 2 Bed 2 Bath Sleeps 6 with an AMAZING Yard, vacation rental in Rose Haven
Stunning Cottage Newly Renovated 2 Bed 2 Bath Sleeps 6 with an AMAZING Yard, vacation rental in Rose Haven

Stunning Cottage Newly Renovated 2 Bed 2 Bath Sleeps 6 with an AMAZING Yard

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Holidays at the Cove  - plenty of space to gather while making memories, vacation rental in Rose Haven
Holidays at the Cove  - plenty of space to gather while making memories, vacation rental in Rose Haven
Holidays at the Cove  - plenty of space to gather while making memories, vacation rental in Rose Haven

Holidays at the Cove - plenty of space to gather while making memories

Rental Home
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
More info
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Bayfront Home with Amazing Rooftop Deck!, vacation rental in Rose Haven
Bayfront Home with Amazing Rooftop Deck!, vacation rental in Rose Haven
Bayfront Home with Amazing Rooftop Deck!, vacation rental in Rose Haven

Bayfront Home with Amazing Rooftop Deck!

Rental Home
5 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
More info
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Waterfront, Water All Around, Peaceful Family Getaway, vacation rental in Rose Haven
Waterfront, Water All Around, Peaceful Family Getaway, vacation rental in Rose Haven
Waterfront, Water All Around, Peaceful Family Getaway, vacation rental in Rose Haven

Waterfront, Water All Around, Peaceful Family Getaway

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Unbelievable Home Newly Renovated Sleeps Up to 9, vacation rental in Rose Haven
Unbelievable Home Newly Renovated Sleeps Up to 9, vacation rental in Rose Haven
Unbelievable Home Newly Renovated Sleeps Up to 9, vacation rental in Rose Haven

Unbelievable Home Newly Renovated Sleeps Up to 9

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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Relax in our cottage within walking distance of Herrington on the Bay events.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Time to book your 2020 Sunset vacation!, vacation rental in Rose Haven
Time to book your 2020 Sunset vacation!, vacation rental in Rose Haven
Time to book your 2020 Sunset vacation!, vacation rental in Rose Haven

Time to book your 2020 Sunset vacation!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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407 Southwinds - Renovated with Direct Chesapeake Bay View near DC and Annapolis, vacation rental in Rose Haven
407 Southwinds - Renovated with Direct Chesapeake Bay View near DC and Annapolis, vacation rental in Rose Haven
407 Southwinds - Renovated with Direct Chesapeake Bay View near DC and Annapolis, vacation rental in Rose Haven

407 Southwinds - Renovated with Direct Chesapeake Bay View near DC and Annapolis

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!, vacation rental in Rose Haven
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!, vacation rental in Rose Haven
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!, vacation rental in Rose Haven

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Crystal Cove Retreat, vacation rental in Rose Haven
Crystal Cove Retreat, vacation rental in Rose Haven
Crystal Cove Retreat, vacation rental in Rose Haven

Crystal Cove Retreat

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Sweet Spot Cottage on the Bay, vacation rental in Rose Haven
Sweet Spot Cottage on the Bay, vacation rental in Rose Haven
Sweet Spot Cottage on the Bay, vacation rental in Rose Haven

Sweet Spot Cottage on the Bay

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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NEW! Secluded Farmhouse on 45 Acres w/ Fire Pit!, vacation rental in Rose Haven
NEW! Secluded Farmhouse on 45 Acres w/ Fire Pit!, vacation rental in Rose Haven
NEW! Secluded Farmhouse on 45 Acres w/ Fire Pit!, vacation rental in Rose Haven

NEW! Secluded Farmhouse on 45 Acres w/ Fire Pit!

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Not to early to think about joining us this Spring and Summer., vacation rental in Rose Haven
Not to early to think about joining us this Spring and Summer., vacation rental in Rose Haven
Not to early to think about joining us this Spring and Summer., vacation rental in Rose Haven

Not to early to think about joining us this Spring and Summer.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Sunrise * Chesapeake, vacation rental in Rose Haven
Sunrise * Chesapeake, vacation rental in Rose Haven
Sunrise * Chesapeake, vacation rental in Rose Haven

Sunrise * Chesapeake

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Adorable waterside cottage with pool Beach community, vacation rental in Rose Haven
Adorable waterside cottage with pool Beach community, vacation rental in Rose Haven
Adorable waterside cottage with pool Beach community, vacation rental in Rose Haven

Adorable waterside cottage with pool Beach community

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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3BR/3BA Waterfront Retreat With Private Pier, vacation rental in Rose Haven
3BR/3BA Waterfront Retreat With Private Pier, vacation rental in Rose Haven
3BR/3BA Waterfront Retreat With Private Pier, vacation rental in Rose Haven

3BR/3BA Waterfront Retreat With Private Pier

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, vacation rental in Rose Haven
BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, vacation rental in Rose Haven
BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, vacation rental in Rose Haven

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

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Clearview - Tilghman Island Cottage, Big Amenities: Pool, Hot Tub, Amazing Views, vacation rental in Rose Haven
Clearview - Tilghman Island Cottage, Big Amenities: Pool, Hot Tub, Amazing Views, vacation rental in Rose Haven
Clearview - Tilghman Island Cottage, Big Amenities: Pool, Hot Tub, Amazing Views, vacation rental in Rose Haven

Clearview - Tilghman Island Cottage, Big Amenities: Pool, Hot Tub, Amazing Views

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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CHESAPEAKE MANSION - HEATED POOL/ 12,000 SQFT/ 30 ACRES, vacation rental in Rose Haven
CHESAPEAKE MANSION - HEATED POOL/ 12,000 SQFT/ 30 ACRES, vacation rental in Rose Haven
CHESAPEAKE MANSION - HEATED POOL/ 12,000 SQFT/ 30 ACRES, vacation rental in Rose Haven

CHESAPEAKE MANSION - HEATED POOL/ 12,000 SQFT/ 30 ACRES

Rental Home
8 bedrooms
10 bathrooms
Sleeps 12
Match: Sleeps
More info
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Indoor pool and spa in contemporary French home secluded in surrounding woods, vacation rental in Rose Haven
Indoor pool and spa in contemporary French home secluded in surrounding woods, vacation rental in Rose Haven
Indoor pool and spa in contemporary French home secluded in surrounding woods, vacation rental in Rose Haven

Indoor pool and spa in contemporary French home secluded in surrounding woods

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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AMAZING WATERFRONT DESTINATION FOR ROMANTIC AND FAMILY VACATIONS., vacation rental in Rose Haven
AMAZING WATERFRONT DESTINATION FOR ROMANTIC AND FAMILY VACATIONS., vacation rental in Rose Haven
AMAZING WATERFRONT DESTINATION FOR ROMANTIC AND FAMILY VACATIONS., vacation rental in Rose Haven

AMAZING WATERFRONT DESTINATION FOR ROMANTIC AND FAMILY VACATIONS.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Lovely Chesapeake Waterfront Flat Just 26 Mi to DC, vacation rental in Rose Haven
Lovely Chesapeake Waterfront Flat Just 26 Mi to DC, vacation rental in Rose Haven
Lovely Chesapeake Waterfront Flat Just 26 Mi to DC, vacation rental in Rose Haven

Lovely Chesapeake Waterfront Flat Just 26 Mi to DC

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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NEW! Coastal Pet-Friendly Cottage <½ Mi to Beaches, vacation rental in Rose Haven
NEW! Coastal Pet-Friendly Cottage <½ Mi to Beaches, vacation rental in Rose Haven
NEW! Coastal Pet-Friendly Cottage <½ Mi to Beaches, vacation rental in Rose Haven

NEW! Coastal Pet-Friendly Cottage <½ Mi to Beaches

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Cozy cottage with expansive backyard and firepit! , vacation rental in Rose Haven
Cozy cottage with expansive backyard and firepit! , vacation rental in Rose Haven
Cozy cottage with expansive backyard and firepit! , vacation rental in Rose Haven

Cozy cottage with expansive backyard and firepit!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Chesapeake Beach Apt. Walk to Bay, Beach & Marina!, vacation rental in Rose Haven
Chesapeake Beach Apt. Walk to Bay, Beach & Marina!, vacation rental in Rose Haven
Chesapeake Beach Apt. Walk to Bay, Beach & Marina!, vacation rental in Rose Haven

Chesapeake Beach Apt. Walk to Bay, Beach & Marina!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Indoor pool and spa located in beautiful Southern Maryland woodlands, vacation rental in Rose Haven
Indoor pool and spa located in beautiful Southern Maryland woodlands, vacation rental in Rose Haven
Indoor pool and spa located in beautiful Southern Maryland woodlands, vacation rental in Rose Haven

Indoor pool and spa located in beautiful Southern Maryland woodlands

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Chesapeake Bay Getaway™ | Waterfront Experience with Pier!, vacation rental in Rose Haven
Chesapeake Bay Getaway™ | Waterfront Experience with Pier!, vacation rental in Rose Haven
Chesapeake Bay Getaway™ | Waterfront Experience with Pier!, vacation rental in Rose Haven

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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BYOB Bring Your Own Bikes!!, vacation rental in Rose Haven
BYOB Bring Your Own Bikes!!, vacation rental in Rose Haven
BYOB Bring Your Own Bikes!!, vacation rental in Rose Haven

BYOB Bring Your Own Bikes!!

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Delightful Pet Friendly Family Home In Great Location, vacation rental in Rose Haven
Delightful Pet Friendly Family Home In Great Location, vacation rental in Rose Haven
Delightful Pet Friendly Family Home In Great Location, vacation rental in Rose Haven

Delightful Pet Friendly Family Home In Great Location

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Chesapeake Spectacular Waterfront- Kayaks, Spa, Pier, vacation rental in Rose Haven
Chesapeake Spectacular Waterfront- Kayaks, Spa, Pier, vacation rental in Rose Haven
Chesapeake Spectacular Waterfront- Kayaks, Spa, Pier, vacation rental in Rose Haven

Chesapeake Spectacular Waterfront- Kayaks, Spa, Pier

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming Herrington Harbor & Bay Cottage, vacation rental in Rose Haven
Charming Herrington Harbor & Bay Cottage, vacation rental in Rose Haven
Charming Herrington Harbor & Bay Cottage, vacation rental in Rose Haven

Charming Herrington Harbor & Bay Cottage

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Spectacular Private Waterview Resort with 4 Master Suites, vacation rental in Rose Haven
Spectacular Private Waterview Resort with 4 Master Suites, vacation rental in Rose Haven
Spectacular Private Waterview Resort with 4 Master Suites, vacation rental in Rose Haven

Spectacular Private Waterview Resort with 4 Master Suites

Rental Home
6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
More info
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