Best Family Escapes - 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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Super 8 By Wyndham Baltimore Northwest From US $87
         

8.2 (1024 Reviews)
Hotel
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  • Parking
  • Wheelchair Accessible
Caton Manor Estate and Pool From US $3,374
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Hidden gem in quiet neighborhood with pool and hot tub From US $687
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Balcony/Terrace
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Lux Escape w/King Bed/Loft/Skyline Views near BLT From US $391
         

10.0 (1 Review)
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  • Pet Friendly
Charm City Luxury 4 Bedroom Brick Home From US $322
         

9.4 (30 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
5 Mi to Inner Harbor: Expansive Family Getaway From US $901
         

9.4 (16 Reviews)
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  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Gwynn Oak

Over 102+ Luxury Places to Stay in or Near Gwynn Oak
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 $462
         

8.0 (9 Reviews)
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Hammock Hideaway From US $437
         

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  • Designated Smoking Area
Charming Baltimore Getaway - 5 Miles to Downtown! From US $428
         

Global Staycation! Scenic Pikesville Family Home From US $332
         

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9.5 (2 Reviews)
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Charming Baltimore Getaway - 5 Miles to Downtown! From US $324
         

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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
Holiday Inn Express Baltimore West - Catonsville by IHG From US $206
         

Hampton Inn & Suites Baltimore/Woodlawn From US $113
         

8.2 (1002 Reviews)
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Hampton Inn & Suites Baltimore/Woodlawn From US $122
         

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7.9 (555 Reviews)
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  • Pet Friendly
Beautiful oasis From US $252
         

New
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Hilltop Retreat w/Pool, Games & Sunroom From US $1,045
         

8.0 (9 Reviews)
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  • Parking
  • Pet Friendly
Howard Johnson by Wyndham Pikesville From US $68
         

4.8 (1004 Reviews)
Hotel
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  • Parking
  • Pool
Beautiful oasis From US $461
         

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  • Air Conditioner
  • Pool
  • Private Pool

Pet-Friendly Vacation Rentals in Gwynn Oak

Over 23+ 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
Cozy and quiet basement apartment pet friendly! From US $227
         

7.4 (6 Reviews)
Apartment
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  • Parking
  • Pet Friendly
Red Roof Inn Baltimore From US $100
         

6.2 (585 Reviews)
Hotel
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  • Parking
  • Pet Friendly
Johnnycake Junction Retreat-Family-Friendly 3BR From US $319
         

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Global Staycation! Scenic Pikesville Family Home From US $275
         

House on the Gwynns Falls From US $216
         

8.6 (34 Reviews)
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  • Parking
  • Pet Friendly
Neat and Discreet-my cul-da-sac is where it's at! From US $183
         

Large Vacation Homes & Villas in Gwynn Oak

Over 14+ Large Vacation Homes & Villas in or Near Gwynn Oak
House on the Gwynns Falls From US $178
         

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9.2 (26 Reviews)
Villa
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  • Pet Friendly
Charming 4 Br 2Ba Duplex From US $203
         

8.8 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Great Area | 5 bedrooms | Large patio From US $298
         

Family and pet friendly house From US $515
         

9.6 (4 Reviews)
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  • Parking
  • Pet Friendly
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)
House
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  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Gwynn Oak

Over 9+ Wheelchair Accessible Vacation Homes in or Near Gwynn Oak
Super 8 by Wyndham Baltimore Northwest From US $109
         

7.6 (688 Reviews)
Hotel
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  • Wheelchair Accessible
Cozy Home in Baltimore From US $140
         

8.6 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Days Inn by Wyndham Baltimore Northwest From US $82
         

5.2 (703 Reviews)
Hotel
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  • Wheelchair Accessible
Days-Inn by Wyndham Baltimore Northwest From US $90
         

7.5 (861 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Charm City Getaway! Workspace Available! Free Parking! From US $193
         

5.0 (4 Reviews)
Condo
  • Air Conditioner
  • Wheelchair Accessible
  • Bedding/Linens
B'more Inn From US $106
         

4.6 (323 Reviews)
Hotel
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  • TV
Red Roof Inn Baltimore From US $86
         

5.8 (230 Reviews)
Hotel
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  • Pet Friendly
Quality Inn Near Pimlico Racetrack From US $87
         

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5.4 (46 Reviews)
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  • Pet Friendly

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

Over 41+ Gwynn Oak Vacation Rentals and Airbnb Places to Stay Under $200
Welcome From US $48
         

4.5 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Royalty Homes - Family style, clean in a safe area. From US $160
         

Quality Inn Windsor Mill - Baltimore From US $85
         

6.6 (1003 Reviews)
Hotel
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  • Parking
  • Designated Smoking Area
Quiet Escape From US $183
         

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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  • Parking
  • TV
Cozy Studio with Private Entrance. From US $181
         

10.0 (1 Review)
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  • Security/Safety
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Ideal Home Away From Home From US $110
         

New
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Instantly Bookable Vacation Homes in Gwynn Oak

Over 29+ Instantly Bookable Vacation Homes in or Near Gwynn Oak
Luxe Private Getaway in the Heart of Baltimore! From US $275
         

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 $267
         

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

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
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

About Gwynn Oak Vacation Rentals

With more than 111 Gwynn Oak vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bestfamilyescapes 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 Bestfamilyescapes 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 758.07 ft² on average, with prices averaging US $279 a night.

Bestfamilyescapes 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 15
Villas 2
Others 1

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

Pro Tip: Bestfamilyescapes makes it easy to compare the best listings on Bestfamilyescapes homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bestfamilyescapes 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 111 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.