Marthas Vineyard Cottages - Vacation Rentals in Deep Hole

One Peace Cottage in Deep Hole From US $203
         

New
House
  • Air Conditioner
  • Parking
  • View
Cozy cottage in a quiet neighborhood close to town, shops, and beach. in Chincoteague From US $88
         

Luxury Places to Stay in Deep Hole

Over 140+ Luxury Places to Stay in or Near Deep Hole

Top-Rated Vacation Rentals with a Pool in Deep Hole

Over 3+ Top-Rated Vacation Rentals with a Pool in or Near Deep Hole

Pet-Friendly Vacation Rentals in Deep Hole

Over 42+ Pet-Friendly Vacation Rentals in or Near Deep Hole
Central Location~Walk 2 Dining! Beach Pass & Gear! in Chincoteague From US $477
         

10.0 (9 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Deep Hole

Over 23+ Large Vacation Homes & Villas in or Near Deep Hole
Gray Pearl in Deep Hole From US $634
         

New
House
  • Air Conditioner
  • Parking
  • View
Island Bay Dreams by Seaside Vacations & Sales in Chincoteague Island From US $317
         

Wheelchair Accessible Vacation Homes in Deep Hole

Over 1+ Wheelchair Accessible Vacation Homes in or Near Deep Hole

Deep Hole Vacation Rentals and Airbnb Places to Stay Under $200

Over 14+ Deep Hole Vacation Rentals and Airbnb Places to Stay Under $200
Ryokan - Water views, Shared Boat Launch! in Deep Hole From US $192
         

New
House
  • Air Conditioner
  • Parking
  • Security/Safety
Pearl in the Pines in Chincoteague From US $122
         

10.0 (58 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Oyster Bay Hideaway on Chincoteague Island! in Chincoteague Island From US $176
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Sunkissed Bliss - 2BR Townhouse - Close to Beach, NO LINENS in Chincoteague From US $186
         

9.6 (21 Reviews)
House
  • Balcony/Terrace
  • Security/Safety
  • Barbecue/Outdoor Cooking

Instantly Bookable Vacation Homes in Deep Hole

Over 69+ Instantly Bookable Vacation Homes in or Near Deep Hole
One Peace Cottage by Seaside Vacations & Sales in Chincoteague Island From US $212
         

10.0 (10 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Cozy 2-bedroom house in Chincoteague in Chincoteague From US $367
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Catch of the Day by Seaside Vacations & Sales in Chincoteague Island From US $279
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety
Heron Point | Kayaks, Bikes & Boat Launch in Chincoteague From US $456
         

About Deep Hole Vacation Rentals

With more than 3 Deep Hole vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Marthasvineyardcottages 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 Deep Hole.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Marthasvineyardcottages Deep Hole, 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 Deep Hole. Places to stay near Deep Hole are 233.33 ft² on average, with prices averaging US $180 a night.

Marthasvineyardcottages makes it easy and safe to find and compare vacation rentals in Deep Hole 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 Deep Hole

Type Count
Cottages 2
Vacation Homes 1

Use these Quick Filters to Find a Vacation Rental in Deep Hole

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

Weather in Deep Hole

View the weather forecast for Deep Hole before booking your Deep Hole 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

Deep Hole Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Deep Hole?

Currently, the total number of properties listed in 2026 is over 3 in the Deep Hole area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Deep Hole.