Middletown, DE, USA Vacation Rentals

United States Maryland Chesapeake City vacation rental compare prices direct by owner 33342637

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Breathtaking views!

5.0 (59)

5 Bedrooms • 12 Guests

$521 avg/night

United States Maryland Galena vacation rental compare prices direct by owner 29475881

Countryside Cottage

4.9 (11)

4 Bedrooms • 8 Guests

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United States Maryland Earleville vacation rental compare prices direct by owner 616922

Historic Mansion - The Anchorage

4.9 (113)

10 Bedrooms • 16 Guests

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United States Maryland Chesapeake City vacation rental compare prices direct by owner 199953

Fall Season @ Old Lock View Chesapeake City MD

5.0 (188)

3 Bedrooms • 8 Guests

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United States Maryland Chesapeake City vacation rental compare prices direct by owner 2558470

Chesapeake City Charm at the Boho House!

5.0 (67)

3 Bedrooms • 6 Guests

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United States Maryland Chesapeake City vacation rental compare prices direct by owner 37150578

Canal views/Walk to Shops/Luxury 2Bed/1.5Bath

5.0 (38)

2 Bedrooms • 4 Guests

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United States Delaware Middletown vacation rental compare prices direct by owner 36129049

Luxury Townhome w/free parking

5.0 (72)

2 Bedrooms • 6 Guests

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United States Maryland Elkton vacation rental compare prices direct by owner 2416740

Short Term Water Oriented Furnished Apartment

5.0 (94)

1 Bedroom • 2 Guests

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United States Maryland Warwick vacation rental compare prices direct by owner 36281319

Saybrook Hall | Pickleball, Pool, and Hot Tub!

4.9 (42)

6 Bedrooms • 15 Guests

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United States Maryland Elkton vacation rental compare prices direct by owner 2394572

Waterfront Retreat for Weekends and More!

4.9 (105)

3 Bedrooms • 8 Guests

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United States Maryland Elkton vacation rental compare prices direct by owner 15383599

Sunset River Shack -amazing waterfront view

4.9 (115)

3 Bedrooms • 6 Guests

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United States Delaware Middletown vacation rental compare prices direct by owner 32959497

Spacious 3 bed/1.5 bath townhome with free parking

4.9 (109)

3 Bedrooms • 6 Guests

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United States Maryland Chesapeake City vacation rental compare prices direct by owner 9369154

HOOK WINE & SINKER sleeps 14 w/ Boat Slip and Inn

4.9 (61)

5 Bedrooms • 16 Guests

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United States Maryland Chesapeake City vacation rental compare prices direct by owner 38572209

Historic Victorian Walkability Chesapeake City

5.0 (26)

5 Bedrooms • 10 Guests

$999 avg/night

United States Maryland Galena vacation rental compare prices direct by owner 25146947

Quiet Country Relaxing Farm

4.8 (63)

3 Bedrooms • 6 Guests

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United States Maryland Elkton vacation rental compare prices direct by owner 28069037

Sunset River Cottage

4.8 (138)

2 Bedrooms • 4 Guests

$374 avg/night

United States Delaware Townsend vacation rental compare prices direct by owner 37036201

NBR Farms Guest House

4.7 (96)

3 Bedrooms • 8 Guests

$265 avg/night

United States Delaware Middletown vacation rental compare prices direct by owner 33543999

Spacious 4 BR Townhouse- Location, Location!

4.2 (10)

4 Bedrooms • 6 Guests

$188 avg/night

United States Delaware Middletown vacation rental compare prices direct by owner 38802190

Rustic Elegance Meets Outdoors

0.0 (0)

2 Bedrooms • 6 Guests

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United States Maryland Chesapeake City vacation rental compare prices direct by owner 1896898

Benson House on Bohemia Ave (Back Deck)

5.0 (129)

1 Bedroom • 2 Guests

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United States Maryland Chesapeake City vacation rental compare prices direct by owner 9824402

Wister Loft: Charm & History with Modern Love.

McReynolds-Woods House -Private 3 Bedroom Home

5.0 (70)

3 Bedrooms • 6 Guests

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United States Maryland Galena vacation rental compare prices direct by owner 33350610

STONE RIVERSIDE COTTAGE is just a few steps from the SASSAFRAS RIVERS edge

5.0 (114)

1 Bedroom • 4 Guests

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United States Maryland Chesapeake City vacation rental compare prices direct by owner 38224640

Modish Cottage - Walk to everything!

5.0 (32)

2 Bedrooms • 4 Guests

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