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2026-08-06
2026-08-07
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Pet-friendly hotels in Deep Hole

'Chincoteague Charm' Escape W/ Bikes & Yard Games!

Deep Hole, United States Show map

The family 'Chincoteague Charm' Escape W/ Bikes & Yard Games! Villa Deep Hole hosts up to 12 guests and provides proximity to the Captain Timothy Hill House, situated only 8 minutes' walk away. More

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Tranquility - Brand New Home In Quiet Location!

5423 Deep Hole Road, Deep Hole, United States Show map

Located merely 1.8 km from the Chincoteague Pony Centre, the 4-bedroom Tranquility - Brand New Home In Quiet Location! Deep Hole provides access to various tourist attractions in the vicinity. This… More

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Cockleshell Cottage - Pet Friendly & Handicap Accessible!

5146 Deep Fern Court, Deep Hole, United States Show map

The 3-bedroom Cockleshell Cottage - Pet Friendly & Handicap Accessible! Deep Hole hosts up to 10 guests and provides proximity to the Captain Timothy Hill House, situated a mere 0.6 km away. More

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Tall Pines - Pet Friendly With Screened Porch!

5328 Oak Drive, Deep Hole, United States Show map

Tall Pines - Pet Friendly With Screened Porch! Deep Hole villa offers proximity to nearby tourist spots, such as Assateague Beach, situated 4.2 km away. More

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Beachgrass Bungalow

5480 Main Street, Deep Hole, United States Show map

Nestled 4.7 km from the 142 - foot - tall Assateague Lighthouse, Beachgrass Bungalow Deep Hole is boasting an indoor water park and a private garden for guests' enjoyment. This accommodation features… More

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Oyster Bay Oasis

5609 Hibiscus Drive, Deep Hole, United States Show map

Oyster Bay Oasis Villa Deep Hole is located 9 minutes' walk from Little Oyster Bay and offers guests to enjoy cycling. Located 4 km from the Veteran's Memorial Park, this holiday home provides Wi-Fi… More

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Sunset Bay Cottage - Main Street Charm With Water Views!

4496 Main Street, Deep Hole, United States Show map

During the stay at Sunset Bay Cottage - Main Street Charm With Water Views! Deep Hole, guests can indulge in mini golf or visit the Captain Timothy Hill House, located a 14-minute walk away. More

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Escape At Deep Hole Hideaway - Pet Friendly Duplex!

5421 Deep Hole Road A, Deep Hole, United States Show map

Situated 9 minutes' walk from Little Oyster Bay, Escape At Deep Hole Hideaway - Pet Friendly Duplex! Villa is ideal for up to 6 guests. More

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Serenity At Deep Hole Hideaway - Pet Friendly!

5421 Deep Hole Road B, Deep Hole, United States Show map

Situated only 0.7 km from Little Oyster Bay, the 2-bedroom Serenity At Deep Hole Hideaway - Pet Friendly! villa is ideal for up to 6 guests. More

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Slack Tide

5379 Cedar Drive, Deep Hole, United States Show map

Slack Tide Deep Hole villa is located about a 25-minute walk from Chincoteague Veteran's Memorial Park and invites guests to join cycling. More

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Wildcat Retreat - Waterfront & Phenomenal Views!

5004 Wildcat Lane, Deep Hole, United States Show map

Situated about 25 minutes' walk from the Chincoteague National Wildlife Refuge, the 4-bedroom Wildcat Retreat - Waterfront & Phenomenal Views! Villa Deep Hole provides access to numerous tourist… More

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Sunshine Daydream - Pet Friendly & Waterfront View!

5412 Coral Court, Deep Hole, United States Show map

Situated 2.3 km from the Chincoteague Pony Centre, the 3-bedroom Sunshine Daydream - Pet Friendly & Waterfront View! Villa Deep Hole entices guests to explore various tourist attractions in the area.… More

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Carriage House

5216 Pine Tree Way, Deep Hole, United States Show map

At Carriage House Villa Deep Hole, guests can enjoy cycling as well as a location a mere 8 minutes' walk from the Captain Timothy Hill House. Located 4.7 km from Oyster Bay, the property provides Wi… More

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Coastal Retreat

6056 Tim Hill Lane, Deep Hole, United States Show map

Providing guests with an indoor water park and a private garden to ensure a memorable stay, Coastal Retreat Villa Deep Hole is 750 m from Little Oyster Bay. The property features opportunities for… More

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The Robinson Family Beach House

4456 Main St, Deep Hole, United States Show map

Staying at The Robinson Family Beach House Deep Hole villa, guests can visit the Museum of Chincoteague, which is nearly a 25-minute walk away. Guests can enjoy cycling at the Deep Hole holiday home,… More

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Grey Heron - Pet Friendly, Waterfront Home With Boat Dock!

5123 Main Street, Deep Hole, United States Show map

Situated within 25 minutes' walk of the Chincoteague Island Library, Grey Heron - Pet Friendly, Waterfront Home With Boat Dock! Deep Hole invites guests to relax at a sun deck. More

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Blue Sea Star - Beautiful Pet Friendly Home!

5199 Pine Tree Way, Deep Hole, United States Show map

Situated just 5 minutes' walk from the Captain Timothy Hill House, the 3-bedroom Blue Sea Star - Beautiful Pet Friendly Home! Deep Hole is ideal for up to 12 guests. More

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Heron'S Cove On Salt Meadow - Pet Friendly, Waterfront Home!

6289 Hancock Lane, Deep Hole, United States Show map

Situated around 25 minutes' walk from the Museum of Chincoteague, the 4-bedroom Heron'S Cove On Salt Meadow - Pet Friendly, Waterfront Home! Deep Hole provides access to numerous tourist attractions… More

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Oyster Catcher - Pet Friendly & Deep Water Access!

5460 Deep Hole Road, Deep Hole, United States Show map

Staying at the 4-bedroom Oyster Catcher - Pet Friendly & Deep Water Access! Deep Hole villa, guests can visit the Deep Hole Creek, which is only 0.7 km away. The Deep Hole holiday home is suitable… More

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Egret'S Walk - Charming Cottage On North Main!

5368 Main Street, Deep Hole, United States Show map

Along with proximity to the Captain Timothy Hill House, only an 8-minute walk away, the 2-bedroom Egret'S Walk - Charming Cottage On North Main! Deep Hole offers opportunities for mini golf in the… More

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Lazy Days - Pet Friendly With Screened Gazebo!

5168 Main Street, Deep Hole, United States Show map

Situated just a few steps from the Captain Timothy Hill House, Lazy Days - Pet Friendly With Screened Gazebo! Deep Hole villa is ideal for up to 7 guests. More

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Grandview - Pet Friendly, Waterfront Home With Dock!

5064 Wildcat Lane, Deep Hole, United States Show map

The 4-bedroom Grandview - Pet Friendly, Waterfront Home With Dock! Deep Hole offers proximity to nearby tourist spots, such as the Chincoteague National Wildlife Refuge, situated nearly 25 minutes'… More

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Langtree - Pet Friendly, Waterfront With Boat Dock!

5388 Sunrise Shore Drive, Deep Hole, United States Show map

Langtree - Pet Friendly, Waterfront With Boat Dock! Villa Deep Hole hosts up to 10 guests and is nestled within 25 minutes' walk of natural sites such as the Maui Jack's Waterpark. Located 2.9 km… More

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Wildcat Haven - Waterfront & Phenomenal Views!

5008 Wildcat Lane, Deep Hole, United States Show map

The 4-bedroom Wildcat Haven - Waterfront & Phenomenal Views! Villa Deep Hole is located 4 km from the Museum of Chincoteague and provides mini golf for active guests. Located 15 minutes by car from… More

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Endless Summer - Pet Friendly With Screened Porch!

7172 Pine Drive, Deep Hole, United States Show map

Up to 9 guests can stay at Endless Summer - Pet Friendly With Screened Porch! Deep Hole villa and enjoy the Piney Island, located a 6-minute walk away. More

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The Blue Crab

6313 Chester Park Drive, Deep Hole, United States Show map

Along with proximity to the Chincoteague Pony Centre, just 5 minutes' walk away, The Blue Crab Villa Deep Hole offers opportunities for cycling in the area. More

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Island Sunrise - Pet Friendly, Waterfront Duplex!

6423 Pine Drive, Deep Hole, United States Show map

Located only a 14-minute walk from the Museum of Chincoteague, the 3-bedroom Island Sunrise - Pet Friendly, Waterfront Duplex! Villa Deep Hole gives access to various tourist sites in the vicinity. More

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Bayside Haven

6112 Hopkins Lane, Deep Hole, United States Show map

Providing guests with an indoor water park and a private garden to ensure a memorable stay, Bayside Haven Villa Deep Hole is just 9 minutes' walk from Little Oyster Bay. This Deep Hole villa features… More

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Our Happy Place - Pet Friendly & Waterfront!

5475 Hibiscus Drive, Deep Hole, United States Show map

With the capacity to host 7 guests, the 3-bedroom Our Happy Place - Pet Friendly & Waterfront! Deep Hole villa is located about 25 minutes on foot from such significant cultural landmarks as the… More

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Star Of The Sea - Renovated Home Located In Town & Pet Friendly!

6318 Chester Park Drive, Deep Hole, United States Show map

Along with proximity to the Chincoteague Pony Centre, only a 5-minute walk away, Star Of The Sea - Renovated Home Located In Town & Pet Friendly! Deep Hole offers opportunities for mini golf in the… More

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Blue Heron

5228 Green Glade Court, Deep Hole, United States Show map

Blue Heron Deep Hole villa is nestled a mere 7 minutes' walk from the Captain Timothy Hill House and can accommodate up to 12 guests. Boasting an indoor water park and a play area, the property is… More

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Cozy Nest - Waterview, Pet Friendly, Screened Porch

5052 N. Main Street, Deep Hole, United States Show map

Situated merely a 5-minute walk from the Captain Timothy Hill House, Cozy Nest - Waterview, Pet Friendly, Screened Porch Deep Hole villa is ideal for up to 6 guests. Located 2.1 km from the… More

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Joint Venture - Pet Friendly & Water Views!

6388 Teal Lane #9, Deep Hole, United States Show map

Joint Venture - Pet Friendly & Water Views! Villa Deep Hole accommodates up to 6 guests and offers proximity to the Chincoteague Pony Centre, located just a 5-minute walk away. More

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Osprey - Pet Friendly, Fireplace!

5497 Hibiscus Drive, Deep Hole, United States Show map

The 3-bedroom Osprey - Pet Friendly, Fireplace! Deep Hole villa can host up to 6 guests, boasting a convenient location approximately 10 minutes' drive from iconic cultural attractions such as the… More

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Windshadow - Waterfront & Pet Friendly!

4635 Main Street, Deep Hole, United States Show map

Windshadow - Waterfront & Pet Friendly! Villa Deep Hole is nestled 9 minutes' walk from the Captain Timothy Hill House and can accommodate up to 8 guests. More

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Egret'S Cove - Pet Friendly W/ Hot Tub!

6272 Hancock Lane, Deep Hole, United States Show map

Egret'S Cove - Pet Friendly W/ Hot Tub! Villa Deep Hole offers proximity to nearby tourist spots, such as the Chincoteague National Wildlife Refuge, situated 2.7 km away. More

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Blue Moon - Pet Friendly And Great Location!

5266 Deep Hole Road, Deep Hole, United States Show map

Situated 750 metres from Little Oyster Bay, Blue Moon - Pet Friendly And Great Location! Villa Deep Hole is ideal for up to 8 guests. Located 25 minutes on foot from the Chincoteague Pony Centre, the… More

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Trembling Bay - Waterfront & A Private Pier!

5181 Sturgis Lane, Deep Hole, United States Show map

Situated only 150 metres from the Captain Timothy Hill House, the 3-bedroom Trembling Bay - Waterfront & A Private Pier! Villa Deep Hole ensures a great leisure experience by offering fishing. More

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Crabby Pines - Pet Friendly Modern Accommodations!

5317 Deep Hole Road, Deep Hole, United States Show map

Up to 8 guests can stay at Crabby Pines - Pet Friendly Modern Accommodations! Deep Hole villa and enjoy the Deep Hole Creek, located about 5 minutes' walk away. More

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