1+ Vacation Rentals Near Galena |
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Unplugged Weekend - Vacation Rentals in Galena

Come enjoy our luxurious 10,000 sq From US $4,257
         

New
Villa
Come enjoy our luxurious 10,000 sq
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  • Pet Friendly

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Luxury Places to Stay in Galena

Over 93+ Luxury Places to Stay in or Near Galena
Bay Cliff: Vacation on the Eastern Shore From US $5,003
         

10.0 (7 Reviews)
House
Bay Cliff: Vacation on the Eastern Shore
  • Air Conditioner
  • Parking
  • Pool

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12 Bedroom Waterfront Historic 1920 Mansion! Pool, hot tub and 400 acres! From US $3,689
         

10.0 (1 Review)
House
12 Bedroom Waterfront Historic 1920 Mansion! Pool, hot tub and 400 acres!
  • Air Conditioner
  • Parking
  • Pool

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Amazing 432-Acre Waterfront Estate ~ Dock ~ Kayaks ~ Beaches ~ Fire Pit From US $2,311
         

10.0 (14 Reviews)
House
Amazing 432-Acre Waterfront Estate ~ Dock ~ Kayaks ~ Beaches ~ Fire Pit
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  • TV

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Private Waterfront Estate with Pool, Private Beach and Dock From US $1,953
         

9.8 (11 Reviews)
House
Private Waterfront Estate with Pool, Private Beach and Dock
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  • Parking
  • Pool

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Thornton From US $1,758
         

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New
House
Thornton
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  • Pet Friendly
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Stunning waterfront villa with indoor pool and kids swing set and play area. From US $1,518
         

9.8 (20 Reviews)
Villa
Stunning waterfront villa with indoor pool and kids swing set and play area.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Guest Lodge | Private Pool | Outdoor Dining | Game Room From US $1,333
         

10.0 (2 Reviews)
House
Guest Lodge | Private Pool | Outdoor Dining | Game Room
  • Air Conditioner
  • Parking
  • Pool

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Historic Manor House on Beautiful Eastern Shore Estate From US $1,260
         

10.0 (27 Reviews)
House
Historic Manor House on Beautiful Eastern Shore Estate
  • Air Conditioner
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  • Pet Friendly

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Top-Rated Vacation Rentals with a Pool in Galena

Over 20+ Top-Rated Vacation Rentals with a Pool in or Near Galena
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock From US $1,025
         

10.0 (61 Reviews)
House
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
  • Air Conditioner
  • Parking
  • Pet Friendly

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BEACH WITHOUT THE BUSTLE From US $220
         

10.0 (36 Reviews)
Condo
BEACH WITHOUT THE BUSTLE
  • Air Conditioner
  • Parking
  • Pool

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Waterfront Lodge packed with Amenities From US $1,097
         

10.0 (3 Reviews)
House
Waterfront Lodge packed with Amenities
  • Air Conditioner
  • Parking
  • Pet Friendly

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A European styled retreat on Marylands Eastern Shore with Private pool From US $327
         

9.8 (79 Reviews)
House
A European styled retreat on Marylands Eastern Shore with Private pool
  • Air Conditioner
  • Parking
  • Pool

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Bella Vista Holiday Family Gatherings in Coastal Maryland! From US $896
         

9.8 (54 Reviews)
House
Bella Vista Holiday Family Gatherings in Coastal Maryland!
  • Air Conditioner
  • Parking
  • Pool

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Holiday Inn Express & Suites Middletown by IHG From US $100
         

9.2 (653 Reviews)
Hotel
Holiday Inn Express & Suites Middletown by IHG
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  • Parking
  • Pool

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Fairfield Inn & Suites by Marriott Middletown From US $117
         

9.2 (309 Reviews)
Hotel
Fairfield Inn & Suites by Marriott Middletown
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  • Pool
  • TV

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Holiday Inn Express & Suites - Middletown by IHG From US $152
         

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8.9 (208 Reviews)
Hotel
Holiday Inn Express & Suites - Middletown by IHG
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  • Pool

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Pet-Friendly Vacation Rentals in Galena

Over 18+ Pet-Friendly Vacation Rentals in or Near Galena
River Heights Retreat From US $1,162
         

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New
House
River Heights Retreat
  • Air Conditioner
  • Pet Friendly
  • View

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Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm! From US $221
         

10.0 (12 Reviews)
Cabin
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Baynnnnnnnn From US $200
         

9.8 (59 Reviews)
Cottage
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Baynnnnnnnn
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  • Pet Friendly

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Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach From US $374
         

9.8 (46 Reviews)
House
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
  • Air Conditioner
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  • Pet Friendly

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Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland. From US $170
         

8.6 (4 Reviews)
House
Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Saybrook Hall | Pickleball, Pool, and Hot Tub! From US $897
         

8.0 (1 Review)
House
Saybrook Hall | Pickleball, Pool, and Hot Tub!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Welcome to the secluded waterfront oasis From US $428
         

New
House
Welcome to the secluded waterfront oasis
  • Air Conditioner
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  • Pet Friendly

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Spacious 4 Bedroom Townhouse From US $182
         

New
House
Spacious 4 Bedroom Townhouse
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  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Galena

Over 14+ Large Vacation Homes & Villas in or Near Galena
Waterfront Millington Vacation Rental with Hot Tub! From US $537
         

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New
House
Waterfront Millington Vacation Rental with Hot Tub!
  • Parking
  • Accessibility
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Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows From US $833
         

10.0 (57 Reviews)
House
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
  • Air Conditioner
  • Parking
  • TV

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Waterfront Millington Vacation Rental w/Hot Tub! From US $528
         

10.0 (7 Reviews)
House
Waterfront Millington Vacation Rental w/Hot Tub!
  • Air Conditioner
  • Parking
  • Security/Safety

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Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful. From US $519
         

9.8 (24 Reviews)
House
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
  • Air Conditioner
  • Parking
  • TV

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8-bedroom house with AC and WiFi in Betterton. 7 minute walk to the beach. From US $595
         

10.0 (1 Review)
House
8-bedroom house with AC and WiFi in Betterton. 7 minute walk to the beach.
  • Air Conditioner
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5 bedroom Historic Victorian by Chester River From US $335
         

9.8 (53 Reviews)
House
5 bedroom Historic Victorian by Chester River
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Waterfront venue on secluded 60 acres with 2 homes great for a family retreat From US $451
         

10.0 (5 Reviews)
Other
Waterfront venue on secluded 60 acres with 2 homes great for a family retreat
  • Air Conditioner
  • Parking
  • TV

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Rambling Victorian Beach House on Maryland's Eastern Shore From US $595
         

10.0 (14 Reviews)
House
Rambling Victorian Beach House on Maryland's Eastern Shore
  • Air Conditioner
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  • TV

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Wheelchair Accessible Vacation Homes in Galena

Over 1+ Wheelchair Accessible Vacation Homes in or Near Galena
Hampton Inn Middletown From US $132
         

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8.5 (178 Reviews)
Hotel
Hampton Inn Middletown
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  • Pet Friendly

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Galena Varoom and Airbnb Places to Stay Under $200

Over 25+ Galena Varoom and Airbnb Places to Stay Under $200
Millington Manor From US $95
         

New
Bed & Breakfast
Millington Manor
  • Parking
  • View
  • Balcony/Terrace

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Peaceful country home away in the wilderness From US $194
         

10.0 (18 Reviews)
House
Peaceful country home away in the wilderness
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Pleasant Hill Motel From US $109
         

7.2 (169 Reviews)
Hotel
Pleasant Hill Motel
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  • Parking
  • TV

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3-bedroom house in charming Middletown with AC From US $88
         

10.0 (2 Reviews)
House
3-bedroom house in charming Middletown with AC
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD From US $142
         

9.8 (52 Reviews)
Apartment
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
  • Air Conditioner
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The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE From US $183
         

9.8 (9 Reviews)
Apartment
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
  • Air Conditioner
  • Parking
  • TV

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Guest Suite for up to 2 in a Victorian on the Chester River From US $78
         

9.6 (19 Reviews)
Apartment
Guest Suite for up to 2 in a Victorian on the Chester River
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  • Parking
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Luxurious and spacious townhome with all necessary amenities awaits your stay. From US $177
         

9.6 (11 Reviews)
House
Luxurious and spacious townhome with all necessary amenities awaits your stay.
  • Air Conditioner
  • Parking
  • TV

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Instantly Bookable Vacation Homes in Galena

Over 22+ Instantly Bookable Vacation Homes in or Near Galena
Your perfect Maryland escape awaits! From US $227
         

10.0 (4 Reviews)
House
Your perfect Maryland escape awaits!
  • Air Conditioner
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Patio & Water Views: Serene Bohemia River Escape! From US $322
         

New
House
Patio & Water Views: Serene Bohemia River Escape!
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Patio & Water Views: Serene Bohemia River Escape! From US $382
         

10.0 (3 Reviews)
House
Patio & Water Views: Serene Bohemia River Escape!
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JVA LUXURY HOUSING From US $589
         

10.0 (1 Review)
House
JVA LUXURY HOUSING
  • Air Conditioner
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Countryside Cottage in Sassafras From US $545
         

10.0 (1 Review)
House
Countryside Cottage in Sassafras
  • Air Conditioner
  • Parking
  • TV

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Amazing Modern house with a full kitchen and parking From US $357
         

9.8 (8 Reviews)
House
Amazing Modern house with a full kitchen and parking
  • Air Conditioner
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  • TV

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Be persuaded to experience this vintage cottage by the Sassa From US $348
         

9.2 (11 Reviews)
Cottage
Be persuaded to experience this vintage cottage by the Sassa
  • Air Conditioner
  • Parking
  • TV

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Heated Pool Private Backyard Home Theater
New
From US $525
         

New
House
Heated Pool Private Backyard Home Theater
  • Air Conditioner
  • Pool
  • TV

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About Galena Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Unpluggedweekend Galena, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Galena. Places to stay near Galena with prices averaging $4,257 a night.

Unpluggedweekend makes it easy and safe to find and compare vacation rentals in Galena with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Galena

Type Count
Villas 1

Use these Quick Filters to Find a Vacation Rental in Galena

★ Pro Tip: Unpluggedweekend makes it easy to compare the best listings on Unpluggedweekend homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Unpluggedweekend homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Galena.

Weather in Galena

View the weather forecast for Galena before booking your Galena Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Galena, MD

Unpluggedweekend offers a large selection of top attractions around Galena. Research things to do on your vacation before you visit Galena.


Dover International Speedway Dover Downs Casino Ripken Stadium Delaware State University Hollywood Casino Dover Mall Washington College Firefly Music Festival Woodland Beach Union Hospital Havre de Grace Promenade Elk Neck State Park Delaware State Visitor Center Delaware Agricultural Museum and Village Harford Memorial Hospital Wheel of Fortune Delaware State Capitol Havre de Grace Decoy Museum Cal Ripken Museum Silver Lake Park

Other Places to Stay Near Galena, MD


Massey 75 Properties