Virginia Beach Attractions - Vacation Rentals in Gwynn Oak

5 Mi to Inner Harbor Expansive Family Getaway From US $647
         

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10.0 (2 Reviews)
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Caton Manor Estate and Pool From US $2,657
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Hidden gem in quiet neighborhood with pool and hot tub From US $629
         

10.0 (1 Review)
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  • Balcony/Terrace
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Cozy Studio with Private Entrance. From US $219
         

10.0 (1 Review)
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  • Security/Safety
  • Bedding/Linens
Charm City Luxury 4 Bedroom Brick Home From US $326
         

9.4 (26 Reviews)
House
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  • TV
  • Balcony/Terrace
5 Mi to Inner Harbor: Expansive Family Getaway From US $846
         

9.4 (16 Reviews)
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  • TV

Luxury Places to Stay in Gwynn Oak

Over 106+ Luxury Places to Stay in or Near Gwynn Oak
Hilltop Retreat w/Pool, Games & Sunroom From US $978
         

7.8 (8 Reviews)
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  • Pet Friendly
Hilltop retreat - Large pool From US $836
         

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✨ Stunning ✨ 7BR Lux House in Baltimore From US $731
         

Massive 5 bedroom with a gameroom! From US $552
         

7.8 (8 Reviews)
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Hammock Hideaway From US $437
         

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Charming Baltimore Getaway - 5 Miles to Downtown! From US $426
         

King-Sized City Oasis From US $412
         

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Top-Rated Vacation Rentals with a Pool in Gwynn Oak

Over 7+ Top-Rated Vacation Rentals with a Pool in or Near Gwynn Oak
Hampton Inn & Suites Baltimore/Woodlawn From US $113
         

8.4 (1003 Reviews)
Hotel
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  • Pool
Holiday Inn Express Baltimore West - Catonsville by IHG From US $206
         

Hampton Inn & Suites Baltimore/Woodlawn From US $123
         

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7.9 (555 Reviews)
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Howard Johnson by Wyndham Pikesville From US $68
         

4.8 (1004 Reviews)
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Beautiful oasis From US $252
         

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Beautiful oasis From US $461
         

New
House
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  • Pool
  • Private Pool

Pet-Friendly Vacation Rentals in Gwynn Oak

Over 26+ Pet-Friendly Vacation Rentals in or Near Gwynn Oak
Comfy and Quaint 15m to Downtown From US $147
         

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9.5 (2 Reviews)
Apartment
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  • Pet Friendly
Red Roof Inn Baltimore From US $91
         

6.2 (572 Reviews)
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  • Pet Friendly
Cozy and quiet basement apartment pet friendly! From US $227
         

7.4 (6 Reviews)
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Johnnycake Junction Retreat-Family-Friendly 3BR From US $306
         

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2-bed, 1 bath Oasis in Gwynn Oak From US $94
         

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House on the Gwynns Falls From US $212
         

8.6 (33 Reviews)
House
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  • Parking
  • Pet Friendly
Neat and Discreet-my cul-da-sac is where it's at! From US $183
         

Charming BohonRetreat/BBQ/Pet Friendly/n10 ppl. From US $326
         

10.0 (3 Reviews)
House
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  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Gwynn Oak

Over 12+ Large Vacation Homes & Villas in or Near Gwynn Oak
Charming 4 Br 2Ba Duplex From US $203
         

8.8 (10 Reviews)
House
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House on the Gwynns Falls From US $178
         

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8.8 (22 Reviews)
Villa
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  • Pet Friendly
Great Area | 5 bedrooms | Large patio From US $309
         

MASSIVE BEAUTIFUL 5 BEDROOM ESTATE, With FREE PARKING From US $464
         

5.0 (2 Reviews)
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  • Child Friendly
Bliss place pet friendly From US $343
         

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Newly Renovated 5 Bedroom Home With Free Parking From US $410
         

8.0 (4 Reviews)
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  • Pet Friendly
68) 4 bedroom home with a Pool! From US $540
         

New
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  • Pet Friendly
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Wheelchair Accessible Vacation Homes in Gwynn Oak

Over 11+ Wheelchair Accessible Vacation Homes in or Near Gwynn Oak
Cozy Home in Baltimore From US $140
         

8.6 (8 Reviews)
House
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  • TV
Super 8 by Wyndham Baltimore Northwest From US $109
         

7.6 (659 Reviews)
Hotel
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  • Parking
  • Wheelchair Accessible
Super 8 By Wyndham Baltimore Northwest From US $82
         

8.2 (952 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Charm City Getaway! Workspace Available! Free Parking! From US $193
         

5.0 (4 Reviews)
Condo
  • Air Conditioner
  • Wheelchair Accessible
  • Bedding/Linens
Days-Inn by Wyndham Baltimore Northwest From US $90
         

7.6 (460 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Days Inn by Wyndham Baltimore Northwest From US $87
         

5.2 (686 Reviews)
Hotel
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  • Wheelchair Accessible
Red Roof Inn Baltimore From US $86
         

5.8 (229 Reviews)
Hotel
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  • Pet Friendly
B'more Inn From US $92
         

4.6 (319 Reviews)
Hotel
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  • TV

Gwynn Oak Vacation Rentals and Airbnb Places to Stay Under $200

Over 46+ Gwynn Oak Vacation Rentals and Airbnb Places to Stay Under $200
Royalty Homes - Family style, clean in a safe area. From US $160
         

Home Away From Home From US $59
         

8.3 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Rodeway Inn Baltimore West From US $70
         

6.4 (1001 Reviews)
Hotel
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  • TV
Quiet Escape From US $151
         

2.0 (2 Reviews)
Apartment
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Peaceful retreat in west Baltimore From US $172
         

2.0 (1 Review)
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Ideal Home Away From Home From US $110
         

New
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The Beatles Blue- Your Best Stay! From US $53
         

Instantly Bookable Vacation Homes in Gwynn Oak

Over 28+ Instantly Bookable Vacation Homes in or Near Gwynn Oak
Luxe Private Getaway in the Heart of Baltimore! From US $284
         

Lovely 2-bedroom house with AC in Baltimore From US $277
         

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Lovely 4 Bedrooms Family home, minutes from Downtown. From US $266
         

New!!! Luxury-2BR-Apt w/ Free Wifi, Parking & Breakfast From US $177
         

8.0 (1 Review)
Apartment
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  • Balcony/Terrace
  • Security/Safety
Cozy home away from home From US $164
         

7.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Gwynn Oak Vacation Rentals

With more than 115 Gwynn Oak vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Virginiabeachattractions 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 Gwynn Oak.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Virginiabeachattractions Gwynn Oak, 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 Gwynn Oak. Places to stay near Gwynn Oak are 739.22 ft² on average, with prices averaging $262 a night.

Virginiabeachattractions makes it easy and safe to find and compare vacation rentals in Gwynn Oak 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 Gwynn Oak

Type Count
Vacation Homes 64
Holiday Apartments 27
Hotels with Suites 19
Villas 2
Others 1

Use these Quick Filters to Find a Vacation Rental in Gwynn Oak

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

Weather in Gwynn Oak

View the weather forecast for Gwynn Oak before booking your Gwynn Oak 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

Gwynn Oak Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Gwynn Oak?
How many vacation rentals are available in Gwynn Oak?

Currently, the total number of properties listed in 2026 is over 115 in the Gwynn Oak area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Gwynn Oak.