Gulf Blue Vacations - Vacation Rentals in Stonewood-Pentwood-Winston

Designer Fashion Loft 1 Bedroom Apartment -Royalty Homes From US $137
         

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5.0 (1 Review)
Apartment
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  • Internet
guesthouse by good neighbor From US $218
         

9.8 (45 Reviews)
Hotel
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  • Balcony/Terrace
  • Security/Safety
Welcome To Tigertown! 4 Bd House From US $468
         

10.0 (11 Reviews)
House
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  • Parking
  • Pet Friendly
1 Block to Penn Station-Baltimore! Urban Studio From US $171
         

Ruscincy’s Rest "minutes drive to Orioles stadium" From US $150
         

Luxury Places to Stay in Stonewood-Pentwood-Winston

Over 248+ Luxury Places to Stay in or Near Stonewood-Pentwood-Winston
Spacious house with finished basement From US $491
         

New
House
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Charmcity Residences- Unit 4 From US $479
         

New
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Charmcity Residences- Unit 3 From US $452
         

Top-Rated Vacation Rentals with a Pool in Stonewood-Pentwood-Winston

Over 3+ Top-Rated Vacation Rentals with a Pool in or Near Stonewood-Pentwood-Winston
Attic Apartment in Leafy Roland Park From US $137
         

9.0 (4 Reviews)
Apartment
  • Air Conditioner
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  • Pool
Luxury Stay on Woodbourne From US $370
         

New
House
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Pet-Friendly Vacation Rentals in Stonewood-Pentwood-Winston

Over 77+ Pet-Friendly Vacation Rentals in or Near Stonewood-Pentwood-Winston
Baltimore Vacation Rental - Near JHU & Art Museum! From US $202
         

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10.0 (2 Reviews)
House
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Oasis Properties WiFi & Parking Ok From US $184
         

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New
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Blue House in Hampden From US $261
         

9.4 (10 Reviews)
Apartment
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Cozy 1 bdrm/1 bath Charles Village/Hopkins Apartment From US $128
         

9.0 (2 Reviews)
Apartment
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  • Parking
  • Pet Friendly
Boho Oasis 2 Bed 1 Bath home in Baltimore City! From US $172
         

8.6 (7 Reviews)
House
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  • Pet Friendly
Historic Charm W/Modern Patio Escape From US $135
         

8.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

Large Vacation Homes & Villas in Stonewood-Pentwood-Winston

Over 23+ Large Vacation Homes & Villas in or Near Stonewood-Pentwood-Winston
Huge Downtown Baltimore home with parking From US $322
         

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9.5 (24 Reviews)
Apartment
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Charmcity Residences- Unit 1 From US $431
         

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Apartment
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Huge Upscale Downtown Penthouse 4Bedrm/3Bath - 5 mins from Penn Station From US $443
         

Spacious PennStation Downtown Penthouse W/Parking From US $304
         

10.0 (1 Review)
Apartment
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  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Stonewood-Pentwood-Winston

Over 11+ Wheelchair Accessible Vacation Homes in or Near Stonewood-Pentwood-Winston
Charming Baltimore Home with Deck and Fire Pit! From US $179
         

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New
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  • Wheelchair Accessible
The Blue Jay From US $107
         

New
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Delta Hotels by Marriott Baltimore North From US $147
         

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8.2 (1004 Reviews)
Hotel
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Delta Hotels by Marriott Baltimore North From US $143
         

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8.2 (161 Reviews)
Hotel
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  • Pet Friendly
The Raven From US $88
         

New
Apartment
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Inn at the Colonnade Baltimore - a DoubleTree by Hilton From US $153
         

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8.2 (1000 Reviews)
Hotel
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  • Designated Smoking Area
The Skyline From US $80
         

New
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The Oriole Nest From US $52
         

New
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Stonewood-Pentwood-Winston Vacation Rentals and Airbnb Places to Stay Under $200

Over 132+ Stonewood-Pentwood-Winston Vacation Rentals and Airbnb Places to Stay Under $200
Chic Baltimore Apartment: 2 Mi to Downtown! From US $133
         

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10.0 (1 Review)
Apartment
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Spacious Roland Park Apt near Hopkins From US $167
         

9.6 (4 Reviews)
Apartment
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  • Parking
  • TV
Motel 6 Baltimore, MD From US $67
         

5.2 (129 Reviews)
Hotel
  • Parking
  • Designated Smoking Area
  • Bedding/Linens
Charle's Village Cozy Studio, From US $143
         

9.0 (9 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Orioles, Ravens, Baltimore Inner Harbor, Towson From US $150
         

Spacious Charles Village unit From US $149
         

8.4 (20 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Royalty Homes - College Style 3 bedroom Apartment From US $150
         

7.6 (13 Reviews)
Apartment
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  • TV
  • Balcony/Terrace
Sol Skyloft w/Earth Lounge n From US $196
         

New
Condo
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area

Instantly Bookable Vacation Homes in Stonewood-Pentwood-Winston

Over 110+ Instantly Bookable Vacation Homes in or Near Stonewood-Pentwood-Winston
6 Mi to Inner Harbor - Family Home w/Fenced Yard! From US $290
         

Treehouse Suite King BR Spa bath Calm Energy From US $225
         

9.8 (6 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Minutes to Downtown & Waterfronts with rooftop deck! From US $274
         

6.0 (2 Reviews)
House
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  • Parking
  • Security/Safety
Baltimore Vacation Rental - Near JHU & Art Museum! From US $246
         

5.4 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

About Stonewood-Pentwood-Winston Vacation Rentals

With more than 257 Stonewood-Pentwood-Winston vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Gulfbluevacations and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Stonewood-Pentwood-Winston.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Gulfbluevacations Stonewood-Pentwood-Winston, 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 Stonewood-Pentwood-Winston. Places to stay near Stonewood-Pentwood-Winston are 495.13 ft² on average, with prices averaging US $254 a night.

Gulfbluevacations makes it easy and safe to find and compare vacation rentals in Stonewood-Pentwood-Winston 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 Stonewood-Pentwood-Winston

Type Count
Vacation Homes 135
Holiday Apartments 110
Hotels 10
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Stonewood-Pentwood-Winston

Pro Tip: Gulfbluevacations makes it easy to compare the best listings on Gulfbluevacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Gulfbluevacations 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 Stonewood-Pentwood-Winston.

Weather in Stonewood-Pentwood-Winston

View the weather forecast for Stonewood-Pentwood-Winston before booking your Stonewood-Pentwood-Winston 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

Stonewood-Pentwood-Winston Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Stonewood-Pentwood-Winston?
How many vacation rentals are available in Stonewood-Pentwood-Winston?

Currently, the total number of properties listed in 2026 is over 257 in the Stonewood-Pentwood-Winston area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Stonewood-Pentwood-Winston.