Deep Hole

Blue Moon - Pet friendly and great location!

Deep Hole
Holiday home 8 people, 4 bedrooms, 3 bathrooms

0.1 km
from center

 

Crabby Pines - Pet friendly modern accommodations!

Deep Hole
Holiday home 8 people, 3 bedrooms, 2 bathrooms

0.2 km
from center

 

Southern Dream - Water views & screened porch!

Deep Hole
Holiday home 8 people, 3 bedrooms, 2 bathrooms

0.3 km
from center

 

An Unfettered View - ranch with boat dock!

Deep Hole
Holiday home 8 people, 2 bedrooms, 2 bathrooms

0.4 km
from center

 

Heron's Cove on Salt Meadow - Pet friendly, waterfront home!

Deep Hole
Holiday home 12 people, 4 bedrooms, 5 bathrooms

0.5 km
from center

 

Escape at Deep Hole Hideaway - Pet friendly duplex!

Deep Hole
Holiday home 6 people, 2 bedrooms, 1 bathroom

0.5 km
from center

 

Serenity at Deep Hole Hideaway - Pet friendly!

Deep Hole
Holiday home 6 people, 2 bedrooms, 1 bathroom

0.5 km
from center

 

Tranquility - Brand new House in quiet location!

Deep Hole
Holiday home 11 people, 4 bedrooms, 2 bathrooms

0.5 km
from center

 

Egret's Cove - Pet friendly with spa!

Deep Hole
Holiday home 11 people, 3 bedrooms, 3 bathrooms

0.5 km
from center

 

beach Bungalow - Pet friendly cottage with views!

Deep Hole
Holiday home 11 people, 3 bedrooms, 3 bathrooms

0.6 km
from center

 

Cedar Cove - Waterfront House with Fire pit!

Deep Hole
Holiday home 12 people, 3 bedrooms, 2 bathrooms

0.7 km
from center

 

Oyster Catcher - Pet friendly & deep water access!

Deep Hole
Holiday home 10 people, 4 bedrooms, 2 bathrooms

0.7 km
from center

 

Highlander - quiet vacation comfort!

Deep Hole
Holiday home 9 people, 3 bedrooms, 2 bathrooms

0.7 km
from center

 

Our Happy Place - Pet friendly & waterfront!

Deep Hole
Holiday home 7 people, 3 bedrooms, 2 bathrooms

0.7 km
from center

 

Star of the Sea - renovated House located in town & pet friendly!

Deep Hole
Holiday home, 195 m² 8 people, 2 bathrooms

0.8 km
from center

 

Sunshine Daydream - Pet friendly & waterfront view!

Deep Hole
Holiday home 8 people, 3 bedrooms, 2 bathrooms

0.8 km
from center

 

Joint Venture - Pet friendly & water views!

Deep Hole
Holiday home 6 people, 2 bathrooms

0.8 km
from center

 

Serenity at Oyster Bay, Water access & firepit!

Deep Hole
Holiday home 10 people, 3 bedrooms, 2 bathrooms

0.9 km
from center

 

Admiral Benbow - contemporary House with shared boat ramp

Deep Hole
Holiday home 8 people, 3 bedrooms, 2 bathrooms

0.9 km
from center

 

Osprey - Pet friendly, fireplace!

Deep Hole
Holiday home 6 people, 3 bedrooms, 2 bathrooms

0.9 km
from center

 

Sea Oats - Water front with boat dock!

Deep Hole
Holiday home 8 people, 2 bathrooms

0.9 km
from center

 

Avalon - waterfront House with fireplace and screened porch

Deep Hole
Holiday home 10 people, 4 bedrooms, 2 bathrooms

0.9 km
from center

 

Charlotte's Morning Sun - Unobstructed Water Views!

Deep Hole
Holiday home 8 people, 4 bedrooms, 4 bathrooms

0.9 km
from center

 

Langtree - Pet friendly, waterfront with boat dock!

Deep Hole
Holiday home 10 people, 3 bathrooms

0.9 km
from center

 

Ryokan - Water views, Shared Boat Launch!

Deep Hole
Holiday home 12 people, 4 bedrooms, 2 bathrooms

0.9 km
from center

 

Sunrise Shore - Waterfront with private swimming-pool & spa!

Deep Hole
Holiday home 16 people, 3 bathrooms

1 km
from center

 

Chincoteague Inn

Chincoteague Island

1.1 km
from Deep Hole

8.5/10
Very good

Chincoteague Charm Escape with Bikes and Yard Games!

Deep Hole
Holiday home, 149 m² 12 people, 4 bedrooms, 3 bathrooms

1.1 km
from center

 

Lavinder House - Waterfront, North Main!

Deep Hole
Holiday home 10 people, 5 bedrooms, 3 bathrooms

1.1 km
from center

 

Mainstay - Outdoor shower & multiple balconies!

Deep Hole
Holiday home 10 people, 3 bedrooms, 2 bathrooms

1.1 km
from center

 

Windshadow - Waterfront & pet friendly!

Deep Hole
Holiday home 8 people, 3 bedrooms, 2 bathrooms

1.1 km
from center

 

Atlantic Shores Inn and Suites

Chincoteague Island

1.2 km
from Deep Hole

7.7/10
Good

Blue Sea Star - Pet Friendly Home!

Deep Hole
Holiday home 12 people, 3 bedrooms, 2 bathrooms

1.2 km
from center

 

Poole's Cove - Waterfront; Main Street!

Deep Hole
Holiday home 6 people, 3 bedrooms, 3 bathrooms

1.2 km
from center

 

Channel Watch - Waterfront House with private Pier!

Deep Hole
Holiday home 7 people, 3 bedrooms, 2 bathrooms

1.2 km
from center

 

Homestead - Located on Main Street with outdoor shower!

Deep Hole
Holiday home 5 people, 3 bedrooms, 2 bathrooms

1.2 km
from center

 

Lazy Days - Pet friendly with screened gazebo!

Deep Hole
Holiday home 7 people, 3 bedrooms, 2 bathrooms

1.2 km
from center

 

Grey Heron - Pet friendly, waterfront House with boat dock!

Deep Hole
Holiday home 8 people, 2 bathrooms

1.2 km
from center

 

Island Sunrise - Pet friendly, waterfront duplex!

Deep Hole
Holiday home 8 people, 3 bedrooms, 2 bathrooms

1.2 km
from center

 

Coastal Cottage - beachy oasis in Oyster Bay!

Deep Hole
Holiday home 8 people, 3 bedrooms, 2 bathrooms

1.3 km
from center

 

Surfers Villa

Chincoteague Island

1.3 km
from Deep Hole

 

Wave Villa

Chincoteague Island

1.3 km
from Deep Hole

8.6/10
Very good

Sand Dollar Villa

Chincoteague Island

1.3 km
from Deep Hole

7.5/10
Good

Crush Villa

Chincoteague Island

1.3 km
from Deep Hole

9/10
Outstanding

Coral Villa @ The Reef

Chincoteague Island

1.3 km
from Deep Hole

9.3/10
Outstanding

Palm Villa @ The Reef

Chincoteague Island

1.3 km
from Deep Hole

7.3/10
Good

LightHouse Villa @ The Reef

Chincoteague Island

1.3 km
from Deep Hole

7.8/10
Good

Sunset Villa

Chincoteague Island

1.3 km
from Deep Hole

 

Sol Villa @ The Reef

Chincoteague Island

1.3 km
from Deep Hole

7/10
Good

Harbor House @ The Reef

Chincoteague Island
Holiday home 8 people, 2 bedrooms, 2 bathrooms

1.3 km
from Deep Hole

10/10
Perfect

beach House @ The Reef

Chincoteague Island
Holiday home 10 people, 3 bedrooms, 1 bathroom

1.3 km
from Deep Hole

10/10
Perfect

beach Haven - Modern Home; close to town!

Chincoteague Island
Holiday home 9 people, 3 bedrooms, 2 bathrooms

1.3 km
from Deep Hole

 

Days Inn by Wyndham Chincoteague Island

Chincoteague Island

1.3 km
from Deep Hole

7.3/10
Good

Trembling Bay - Waterfront & a private pier!

Deep Hole
Holiday home 6 people, 3 bedrooms, 2 bathrooms

1.3 km
from center

 

Jellystone Park Chincoteague Island

Chincoteague Island
2 holiday home 4 people (total 8 people)

1.3 km
from Deep Hole

7.9/10
Good

Tall Pines - Pet friendly with screened porch!

Deep Hole
Holiday home 6 people, 2 bedrooms, 1 bathroom

1.3 km
from center

 

Chincoteague Island Cottage about 2 Mi to beaches

Chincoteague Island
Holiday home, 111 m² 5 people, 2 bedrooms, 1 bathroom

1.3 km
from Deep Hole

8/10
Very good

Belle of the Bay - Custom Waterfront Home!

Deep Hole
Holiday home 8 people, 4 bedrooms, 2 bathrooms

1.4 km
from center

 

Hailey's Round- New & Unique House with Water Access!

Deep Hole
Holiday home 9 people, 3 bedrooms, 2 bathrooms

1.4 km
from center

 

Cozy Nest - Waterview, Pet Friendly, Screened Porch

Deep Hole
Holiday home 6 people, 2 bedrooms, 2 bathrooms

1.4 km
from center

 

Southern Exposure - Waterfront with boat dock!

Deep Hole
Holiday home 7 people, 4 bedrooms, 2 bathrooms

1.4 km
from center

 

Cockleshell Cottage - Pet friendly & Handicap Accessible!

Deep Hole
Holiday home 10 people, 3 bedrooms, 3 bathrooms

1.4 km
from center

 

Windsor House - In town historic charm

Chincoteague Island
Holiday home 8 people, 3 bedrooms, 2 bathrooms

1.4 km
from Deep Hole

 

Island Resort

Chincoteague Island

1.4 km
from Deep Hole

9/10
Outstanding

Bue Crab Bungalow - Charming in-town cottage!

Birch Town
Holiday home 5 people, 2 bedrooms, 1 bathroom

1.5 km
from Deep Hole

8.3/10
Very good

Blue Marlin - Pet friendly with Private Dock!

Chincoteague Island
Holiday home 8 people, 3 bedrooms, 2 bathrooms

1.5 km
from Deep Hole

 

Endless Summer - Pet friendly with screened porch!

Deep Hole
Holiday home 9 people, 4 bedrooms, 2 bathrooms

1.5 km
from center

 

Shady Side - Water access, screened porch!

Deep Hole
Holiday home 10 people, 4 bedrooms, 2 bathrooms

1.5 km
from center

 

Conch Shell - Waterfront villa with wrap around deck!

Deep Hole
Holiday home 6 people, 3 bedrooms, 1 bathroom

1.5 km
from center

 

Oasis on Main - Charming Victorian on Main Street!

Chincoteague Island
Holiday home 11 people, 3 bedrooms, 1 bathroom

1.5 km
from Deep Hole

 

Donovan's Reef - Pet friendly, In Town!

Chincoteague Island
Holiday home 8 people, 3 bedrooms, 2 bathrooms

1.6 km
from Deep Hole

 

Gone Coastal - Pet friendly with screened porch!

Birch Town
Holiday home 6 people, 2 bathrooms

1.6 km
from Deep Hole

 

2 Mi to Downtown Tranquil Abode in Chincoteague!

Chincoteague Island
Holiday home, 135 m² 8 people, 3 bedrooms, 2 bathrooms

1.6 km
from Deep Hole

 

My Island Escape - North Main & private dock!

Deep Hole
Holiday home 7 people, 3 bedrooms, 2 bathrooms

1.6 km
from center

 

Egret's Walk - Charming Cottage on North Main!

Deep Hole
Holiday home 5 people, 2 bedrooms, 1 bathroom

1.6 km
from center

 

Inn at Poplar Corner B & B on Chincoteague Island

Chincoteague Island

1.6 km
from Deep Hole

9.2/10
Outstanding

A 'Teague of Our Own - Pet friendly & In town!

Chincoteague Island
Holiday home 8 people, 3 bedrooms, 1 bathroom

1.6 km
from Deep Hole

 

Cottage w Private Creek, Sunroom, Fire Pit, & WiFi

Chincoteague Island
Holiday home, 131 m² 6 people, 3 bedrooms, 2 bathrooms

1.6 km
from Deep Hole

8.1/10
Very good

Dragonfly Point - Waterfront House w boat dock & deck!

Deep Hole
Holiday home 8 people, 4 bedrooms, 3 bathrooms

1.6 km
from center

 

Shady Grove - Water views, fireplace!

Deep Hole
Holiday home 8 people, 4 bedrooms, 2 bathrooms

1.6 km
from center

 

Key West Cottages

Chincoteague Island
8 villas, 34 to 57 m² 2 to 5 people (total 30 people)

1.7 km
from Deep Hole

9.6/10
Outstanding

Kellys Cottage

Chincoteague Island
Holiday home 7 people, 3 bedrooms, 1 bathroom

1.7 km
from Deep Hole

 

The Inn On Main

Chincoteague Island

1.7 km
from Deep Hole

8.6/10
Very good

Bayside Bliss - Waterfront home, views

Deep Hole
Holiday home 10 people, 3 bathrooms

1.7 km
from center

 

Shreiner's Tradition - In Town, Pet friendly!

Chincoteague Island
Holiday home 6 people, 2 bedrooms, 2 bathrooms

1.7 km
from Deep Hole

 

Blake's Purple Point - Waterfront splendor!

Deep Hole
Holiday home 12 people, 4 bedrooms, 3 bathrooms

1.7 km
from center

 

June's Retreat - Waterfront; Boat dock!

Deep Hole
Holiday home 10 people, 4 bedrooms, 5 bathrooms

1.7 km
from center

 

Hampton Inn & Suites Chincoteague-Waterfront, Va

Chincoteague Island

1.7 km
from Deep Hole

9.2/10
Outstanding

Lottie's Lookout - In town; Pet friendly; Fire pit!

Chincoteague Island
Holiday home 8 people, 3 bedrooms, 3 bathrooms

1.7 km
from Deep Hole

 

All Done - Pet Friendly; New for 2024!

Birch Town
Holiday home, 178 m² 8 people, 3 bedrooms, 3 bathrooms

1.7 km
from Deep Hole

 

Blue Pointe Bayside - Cozy, Waterfront home!

Deep Hole
Holiday home 8 people, 3 bedrooms, 3 bathrooms

1.8 km
from center

 

Casa del Mar - Pet friendly with spa!

Chincoteague Island
Holiday home 12 people, 5 bedrooms, 4 bathrooms

1.8 km
from Deep Hole

 

Waterman's Daughter - Pet friendly; Water access!

Birch Town
Holiday home 6 people, 3 bedrooms, 3 bathrooms

1.8 km
from Deep Hole

 

Comfort Suites Chincoteague Island Bayfront Resort

Chincoteague Island

1.8 km
from Deep Hole

9.2/10
Outstanding

Shore Thing on Oyster Bay - Waterfront, Boat Dock!

Deep Hole
Holiday home 8 people, 4 bedrooms, 3 bathrooms

1.8 km
from center

 

Chamallow - Waterfront House with Floating dock!

Deep Hole
Holiday home 12 people, 2 bathrooms

1.9 km
from center

 

Piney Island Paradise - Waterfront with pier & patio!

Birch Town
Holiday home 8 people, 3 bedrooms, 2 bathrooms

1.9 km
from Deep Hole

 

Off Belay - Creek View

Deep Hole
Holiday home 8 people, 4 bedrooms, 3 bathrooms

1.9 km
from center

 

Channel Bass Inn and Restaurant

Chincoteague Island
6 bedrooms (total 23 people)

1.9 km
from Deep Hole

8.2/10
Very good

Sea Charm - Downtown, Screened porch!

Chincoteague Island
Holiday home 8 people, 3 bedrooms, 2 bathrooms

2 km
from Deep Hole

 

Sea Shell Motel

Chincoteague Island

2 km
from Deep Hole

9.4/10
Outstanding

Cottage with Yard in Dtwn Chincoteague!

Chincoteague Island
Holiday home, 130 m² 6 people, 2 bedrooms, 1 bathroom

2 km
from Deep Hole

 

Utter East - great House with large screened porch and firepit next to the pond

Birch Town
Holiday home 10 people, 4 bedrooms, 2 bathrooms

2.1 km
from Deep Hole

 

Bay Daze - Waterfront townhome w private boat dock!

Chincoteague Island
Holiday home 6 people, 2 bedrooms, 2 bathrooms

2.1 km
from Deep Hole

 

Magic Moments - Waterfront on Marsh Island!

Chincoteague Island
Holiday home 6 people, 2 bedrooms, 1 bathroom

2.1 km
from Deep Hole

 

Sundance at Marsh Island - Waterfront townhome!

Chincoteague Island
Holiday home 4 people, 1 bathroom

2.1 km
from Deep Hole

 

Horseshoe Hideaway - Cozy House with screened porches!

Birch Town
Holiday home 8 people, 2 bathrooms

2.1 km
from Deep Hole

 

Horseshoe Haven

Chincoteague Island
Apartment, 93 m² 8 people, 3 bedrooms, 2 bathrooms

2.2 km
from Deep Hole

 

Chincoteague Apartment with Deck Walk to Waterfront

Chincoteague Island
Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom

2.2 km
from Deep Hole

 

Castlebar - Luxury waterfront House with Private dock!

Deep Hole
Holiday home 10 people, 5 bedrooms, 3 bathrooms

2.3 km
from center

 

Hidden Treasure - Waterfront House with boat dock!

Deep Hole
Holiday home 10 people, 4 bedrooms, 3 bathrooms

2.3 km
from center

 

Olive Ponies - Upper level with water Views!

Birch Town
Holiday home 9 people, 4 bedrooms, 1 bathroom

2.3 km
from Deep Hole

 

Shell Cottage - Pet friendly, spa, Fenced yard!

Birch Town
Holiday home 8 people, 4 bedrooms, 2 bathrooms

2.3 km
from Deep Hole

 

Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

Chincoteague Island

2.3 km
from Deep Hole

8.9/10
Very good

Hill House - Pet friendly, In town with water views!

Chincoteague Island
Holiday home 9 people, 4 bedrooms, 2 bathrooms

2.4 km
from Deep Hole

 

LightHouse View - Water views & shared swimming-pool !

Birch Town
Holiday home 8 people, 3 bedrooms, 2 bathrooms

2.4 km
from Deep Hole

 

Morning Memories - Pet friendly, shared swimming-pool & dock!

Birch Town
Holiday home 6 people, 2 bedrooms, 2 bathrooms

2.4 km
from Deep Hole

 

Vast Views - Pet friendly & a shared swimming-pool !

Birch Town
Holiday home 8 people, 2 bedrooms, 2 bathrooms

2.4 km
from Deep Hole

 

LightHouse Estates 8 - Water views & shared swimming-pool !

Birch Town
Holiday home 6 people, 2 bedrooms, 2 bathrooms

2.4 km
from Deep Hole

 

Sunset Bay Villa 206 - Waterfront & shared swimming-pool !

Chincoteague Island
Holiday home 8 people, 3 bedrooms, 2 bathrooms

2.5 km
from Deep Hole

 

Sunset Bay Villa 208 - Pet friendly & includes a boat slip!

Chincoteague Island
Holiday home 8 people, 3 bedrooms, 2 bathrooms

2.5 km
from Deep Hole

 

Sunset Bay Villa 212 - Pet friendly & waterfront view!

Chincoteague Island
Holiday home 6 people, 3 bedrooms, 2 bathrooms

2.5 km
from Deep Hole

 

Sundance - In town with screened porch!

Birch Town
Holiday home 9 people, 4 bedrooms, 3 bathrooms

2.5 km
from Deep Hole

 

Wildcat Haven - Waterfront & phenomenal views!

Deep Hole
Holiday home 10 people, 4 bedrooms, 4 bathrooms

2.5 km
from center

 

Sunset Bay Villa 116 - Waterfront with shared swimming-pool !

Chincoteague Island
Holiday home 8 people, 3 bedrooms, 2 bathrooms

2.5 km
from Deep Hole

 

Sunset Bay Villa 119 - Waterfront & shared swimming-pool !

Chincoteague Island
Holiday home 8 people, 3 bedrooms, 2 bathrooms

2.5 km
from Deep Hole

 

Sunset Bay Villa 312 - Waterfront & includes a boat slip!

Chincoteague Island
Holiday home 8 people, 3 bedrooms, 2 bathrooms

2.5 km
from Deep Hole

 

Sunset Bay Villa 221 - Waterfront, swimming-pool , Gym!

Chincoteague Island
Holiday home 8 people, 3 bedrooms, 2 bathrooms

2.5 km
from Deep Hole

 

3 Mi to beach Waterfront Condo in Chincoteague!

Chincoteague Island
Apartment, 82 m² 6 people, 2 bedrooms, 2 bathrooms

2.6 km
from Deep Hole

10/10
Perfect

Sunset Bay Villa 118 - Waterfront, Deep-water boat slip!

Chincoteague Island
Holiday home 7 people, 3 bedrooms, 2 bathrooms

2.6 km
from Deep Hole

 

beach Bay Pony Place with Ponies 1 Mi to Water!

Chincoteague Island
Holiday home, 149 m² 5 people, 2 bedrooms, 2 bathrooms

2.6 km
from Deep Hole

10/10
Perfect

Marina Bay Hotel & Suites, Ascend Hotel Collection

Chincoteague Island

2.6 km
from Deep Hole

8.3/10
Very good

Serendipity - On main Street with screened porch!

Chincoteague Island
Holiday home 6 people, 1 bathroom

2.6 km
from Deep Hole

 

Stingray - Waterfront & waterside balcony!

Birch Town
Holiday home 6 people, 2 bedrooms, 2 bathrooms

2.6 km
from Deep Hole

 

Anchor Inn

Chincoteague Island

2.7 km
from Deep Hole

8/10
Very good

Charlie's Bayside Retreat - Pet friendly, In town!

Chincoteague Island
Holiday home 8 people, 3 bedrooms, 2 bathrooms

2.7 km
from Deep Hole

 

Waterside Inn

Chincoteague Island

2.7 km
from Deep Hole

8.5/10
Very good

Wildcat Retreat - Waterfront & phenomenal Views!

Deep Hole
Holiday home 10 people, 4 bedrooms, 4 bathrooms

2.8 km
from center

 

Dockside - Waterfront Condo with boat Dock!

Birch Town
Holiday home 8 people, 3 bathrooms

2.8 km
from Deep Hole

 

Island Thyme - spa & carnival location!

Chincoteague Island
Holiday home 8 people, 3 bedrooms, 2 bathrooms

2.8 km
from Deep Hole

 

Pony View - Pet friendly, waterfront with boat slip!

Birch Town
Holiday home 8 people, 3 bedrooms, 3 bathrooms

2.8 km
from Deep Hole

 

The Haven - Waterfront with private dock!

Birch Town
Holiday home 8 people, 3 bathrooms

2.9 km
from Deep Hole

 

Heron Landing - In town, coastal cottage!

Birch Town
Holiday home 6 people, 2 bedrooms, 1 bathroom

3 km
from Deep Hole

 

Dancing Waters at Sea Tag - Waterfront Condo!

Birch Town
Holiday home 6 people, 2 bedrooms, 1 bathroom

3 km
from Deep Hole

 

Sea La Vie - Duplex, Shared swimming-pool !

Chincoteague Island
Holiday home 8 people, 2 bathrooms

3 km
from Deep Hole

 

La Dolce Vita - Waterfront with boat dock!

Deep Hole
Holiday home 10 people, 4 bedrooms, 4 bathrooms

3 km
from center

 

Seas the Day - Water views, Shared swimming-pool !

Chincoteague Island
Holiday home 8 people, 2 bathrooms

3 km
from Deep Hole

 

La Vie - Waterfront, boat dock & swimming-pool !

Chincoteague Island
Holiday home 6 people, 3 bedrooms, 2 bathrooms

3 km
from Deep Hole