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2026-11-06
2026-11-07
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Pet-friendly hotels in Deep Hole

Serenity At Deep Hole Hideaway - Pet Friendly!

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

The 2-bedroom Serenity At Deep Hole Hideaway - Pet Friendly! villa is nestled only a 9-minute walk from Little Oyster Bay and can accommodate up to 6 guests. Located in the vicinity of Oyster Bay… More

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

Deep Hole, United States Show map

The family-friendly 'Chincoteague Charm' Escape W/ Bikes & Yard Games! Villa Deep Hole hosts up to 12 guests a mere 8 minutes' walk from Captain Timothy Hill House and offers rental hire. More

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Tranquility - Brand New Home In Quiet Location!

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

The 4-bedroom Tranquility - Brand New Home In Quiet Location! Deep Hole hosts up to 11 guests and provides proximity to Little Oyster Bay, situated merely 0.7 km away. Providing guests with Wi-Fi and… More

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Cockleshell Cottage - Pet Friendly & Handicap Accessible!

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

The 2-bedroom Cockleshell Cottage - Pet Friendly & Handicap Accessible! Deep Hole hosts up to 10 guests and provides proximity to Captain Timothy Hill House, situated a mere 0.6 km away. Providing… More

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Tall Pines - Pet Friendly With Screened Porch!

5328 Oak Drive, Deep Hole, United States Show map

Offering a location 4.2 km from Assateague Beach, the 2-bedroom Tall Pines - Pet Friendly With Screened Porch! Deep Hole villa gives access to various tourist spots in the area. With a maximum… More

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Beachgrass Bungalow

5480 Main Street, Deep Hole, United States Show map

Nestled 4.7 km from the historic red-&-white Assateague Lighthouse, the 2-bedroom Beachgrass Bungalow Deep Hole is boasting an aqua park and a golf course for guests' enjoyment. Located approximately… More

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Blue Sea Star - Beautiful Pet Friendly Home!

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

The 3-bedroom Blue Sea Star - Beautiful Pet Friendly Home! Deep Hole is nestled about a 5-minute walk from Captain Timothy Hill House and can accommodate up to 12 guests. Located 4.2 km from… 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 Captain Timothy Hill House, located a 14-minute walk away. The 3… More

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Escape At Deep Hole Hideaway - Pet Friendly Duplex!

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

Featuring island tours to make your visit more entertaining, Escape At Deep Hole Hideaway - Pet Friendly Duplex! Villa is a 9-minute walk from Deep Hole Creek. The 2-bedroom holiday home hosts up to… More

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Slack Tide

5379 Cedar Drive, Deep Hole, United States Show map

Offering an aqua park and a golf course for guests' leisure, the 3-bedroom Slack Tide Deep Hole villa is situated about a 25-minute walk from Chincoteague Veteran's Memorial Park. Offering island… More

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Wildcat Retreat - Waterfront & Phenomenal Views!

5004 Wildcat Lane, Deep Hole, United States Show map

Offering a location about 25 minutes' walk from Chincoteague National Wildlife Refuge, the 4-bedroom Wildcat Retreat - Waterfront & Phenomenal Views! Villa Deep Hole gives access to various tourist… More

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Sunshine Daydream - Pet Friendly & Waterfront View!

5412 Coral Court, Deep Hole, United States Show map

Nestled 2.3 km from Chincoteague Pony Centre, the 3-bedroom Sunshine Daydream - Pet Friendly & Waterfront View! Villa Deep Hole entices guests to explore various tourist destinations nearby. Offering… More

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Carriage House

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

Situated nearly a 25-minute walk from Chincoteague Pony Centre, the 4-bedroom Carriage House Villa Deep Hole offers guests to enjoy an aqua park and a golf course. The holiday home features… More

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Coastal Retreat

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

The 3-bedroom Coastal Retreat Villa Deep Hole is nestled merely 9 minutes' walk from Little Oyster Bay and can accommodate up to 8 guests. Located 3.8 km from Veteran's Memorial Park, the villa comes… More

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The Robinson Family Beach House

4456 Main St, Deep Hole, United States Show map

Staying at the 3-bedroom The Robinson Family Beach House Deep Hole villa, guests can visit Museum of Chincoteague, which is nearly a 25-minute walk away. Offering island tours, the Deep Hole holiday… More

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

5123 Main Street, Deep Hole, United States Show map

Staying at Grey Heron - Pet Friendly, Waterfront Home With Boat Dock! Deep Hole, guests can easily reach Chincoteague Island Library, located nearly a 25-minute walk away. Offering island tours, this… More

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Heron'S Cove On Salt Meadow | Bayfront Views, Dock, King Suites, Fireplace + Pet Friendly

6289 Hancock Lane, Deep Hole, United States Show map

The 4-bedroom Heron'S Cove On Salt Meadow | Bayfront Views, Dock, King Suites, Fireplace + Pet Friendly Deep Hole villa is located around 25 minutes' walk from Museum of Chincoteague, giving access… 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 Deep Hole Creek, which is only 0.7 km away. Offering island tours, the Deep Hole holiday… More

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Egret'S Walk | Peaceful Marsh & Creek View Cottage North Of Town W/ Wildlife Views & Pet Friendly

5368 Main Street, Deep Hole, United States Show map

The 2-bedroom Egret'S Walk | Peaceful Marsh & Creek View Cottage North Of Town W/ Wildlife Views & Pet Friendly Deep Hole hosts up to 5 guests and provides proximity to Captain Timothy Hill House… More

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Lazy Days - Pet Friendly With Screened Gazebo!

5168 Main Street, Deep Hole, United States Show map

Featuring island tours to make your visit more entertaining, Lazy Days - Pet Friendly With Screened Gazebo! Deep Hole villa is 25 minutes' walk from Maui Jack's Waterpark. The 3-bedroom holiday home… 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 is located around 25 minutes' walk from Chincoteague National Wildlife Refuge, giving access to various tourist spots… More

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Langtree - Pet Friendly, Waterfront With Boat Dock!

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

The 3-bedroom 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 Maui Jack's Waterpark. Located… More

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Wildcat Haven - Waterfront & Phenomenal Views!

5008 Wildcat Lane, Deep Hole, United States Show map

Featuring island tours to make your visit more entertaining, the 4-bedroom Wildcat Haven - Waterfront & Phenomenal Views! Villa Deep Hole is about 6 km from the 142 - foot - tall Assateague… 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 Piney Island, located a 6-minute walk away. Located 1.8 km from Chincoteague National Wildlife… More

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The Blue Crab

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

The 3-bedroom The Blue Crab Villa Deep Hole, located approximately 5 minutes' walk from The Brant Gift Shop, can host up to 9 guests. The property boasts an aqua park and a golf course, while Museum… More

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Island Sunrise - Pet Friendly, Waterfront Duplex!

6423 Pine Drive, Deep Hole, United States Show map

Nestled just a 14-minute walk from Museum of Chincoteague, the 3-bedroom Island Sunrise - Pet Friendly, Waterfront Duplex! Villa Deep Hole entices guests to explore various tourist destinations… More

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Bayside Haven

6112 Hopkins Lane, Deep Hole, United States Show map

The 2-bedroom Bayside Haven Villa Deep Hole is located approximately 25 minutes' walk from Chincoteague Island Library and welcomes its guests to enjoy cycling. Offering island tours, the property… 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 around 25 minutes on foot from such significant cultural landmarks as Museum… 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 Chincoteague Pony Centre, only a 5-minute walk away, the 3-bedroom Star Of The Sea - Renovated Home Located In Town & Pet Friendly! Deep Hole offers opportunities for mini… More

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Blue Heron

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

The 3-bedroom Blue Heron Deep Hole villa is located just 7 minutes' walk from Captain Timothy Hill House and invites guests to enjoy island tours. The property features opportunities for mini golf… More

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Cozy Nest - Waterview, Pet Friendly, Screened Porch

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

Featuring island tours to make your visit more entertaining, Cozy Nest - Waterview, Pet Friendly, Screened Porch Deep Hole villa is 25 minutes' walk from Chincoteague Pony Centre. The 2-bedroom… 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, located nearly 5 minutes' walk from The Brant Gift Shop, can host up to 6 guests. Providing guests with Wi-Fi and parking, this Deep Hole… More

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Osprey - Pet Friendly, Fireplace!

5497 Hibiscus Drive, Deep Hole, United States Show map

Staying at the 3-bedroom Osprey - Pet Friendly, Fireplace! Deep Hole villa, guests can visit Chincoteague Pony Centre, which is nearly 10 minutes' drive away. Offering island tours, this Deep Hole… More

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Windshadow - Waterfront & Pet Friendly!

4635 Main Street, Deep Hole, United States Show map

Featuring island tours to make your visit more entertaining, Windshadow - Waterfront & Pet Friendly! Villa Deep Hole is 25 minutes' walk from Maui Jack's Waterpark. The 3-bedroom holiday home hosts… More

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Egret'S Cove | Bayfront Oyster Bay Retreat W/ Hot Tub, Screened Porch, Dock & Fenced Yard For Pets

6272 Hancock Lane, Deep Hole, United States Show map

Situated 10 minutes' drive from Chincoteague National Wildlife Refuge, Egret'S Cove | Bayfront Oyster Bay Retreat W/ Hot Tub, Screened Porch, Dock & Fenced Yard For Pets Deep Hole villa provides… More

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Blue Moon - Pet Friendly And Great Location!

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

Blue Moon - Pet Friendly And Great Location! Villa Deep Hole is nestled 750 metres from Little Oyster Bay and can accommodate up to 8 guests. Located 25 minutes' stroll from Chincoteague Pony Centre,… More

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Trembling Bay - Waterfront & A Private Pier!

5181 Sturgis Lane, Deep Hole, United States Show map

The 2-bedroom Trembling Bay - Waterfront & A Private Pier! Villa Deep Hole hosts up to 6 guests and provides proximity to Captain Timothy Hill House, situated merely 150 metres away. Providing guests… 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 Deep Hole Creek, located about 5 minutes' walk away. Located 2.3 km from Captain Timothy Hill… More

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