Deep Hole Vacation Rentals

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Browse Select Deep Hole Vacation Homes

Our top choices for Deep Hole vacation homes

Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!

9.4 out of 10, Exceptional, (12)
"Went for a guys trip and enjoyed it "
The price is CA $207
CA $546 total
includes taxes & fees
Sep 4 - Sep 5
Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!

Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great stay. Great host. Very clean place. Couldn’t of asked for a better host and house ! "
The price is CA $179
CA $395 total
includes taxes & fees
Sep 22 - Sep 23
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Heron's Roost-Waterfront, Oyster Bay

6.0 out of 10, (1)
"After we cleaned some areas we could manage,we were a little surprised that it didnt say on the website that there is a spiral stairs. Also some of the furniture is outdated and noticed a chair was ziptied so that wasnt quite comfortable knowing.."
The price is CA $620
CA $1,017 total
includes taxes & fees
Sep 16 - Sep 17
Heron's Roost-Waterfront, Oyster Bay

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (169)
"excellent place to stay on the water"
The price is CA $309
CA $347 total
includes taxes & fees
Sep 7 - Sep 8
Blufin Bungalows & Marina

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

9.6 out of 10, Exceptional, (42)
"We enjoyed our stay at Waterside. Location was perfect and host was very responsive to questions. A great rental for a few friends and/or family."
The price is CA $145
CA $554 total
includes taxes & fees
Sep 1 - Sep 2
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Stunning waterfront panoramic view getaway house

10.0 out of 10, Exceptional, (53)
"The roundhouse was amazing on many levels, figuratively and literally. There are many creature, comforts throughout this sprawling home and the views were serene and relaxing, and the couches and beds were comfy! And the host was very helpful and accommodating. Highly recommend would definitely stay here again."
The price is CA $164
CA $684 total
includes taxes & fees
Sep 1 - Sep 2
Stunning waterfront panoramic view getaway house

Blue Heron-Closest Neighborhood to Beach w/shared community water access!

10.0 out of 10, Exceptional, (1)
"The cottage was perfect for us! Clean and cute and plenty of room to move around. The porch was excellent for having cousins visit and host a game night. The bedrooms were cosy and inviting."
The price is CA $414
CA $726 total
includes taxes & fees
Sep 13 - Sep 14
Blue Heron-Closest Neighborhood to Beach w/shared community water access!

The purple door at the bay.

9.2 out of 10, Wonderful, (51)
"Property was slightly run down and had no driveway (just grass). It was in a great neighborhood with a beautiful view. We had to take the trash 15 minutes south when leaving (in the opposite direction of home for us). It was good enough for us to relax and cook but a slight bit expensive for its outdated condition though."
The price is CA $241
CA $640 total
includes taxes & fees
Sep 25 - Sep 26
The purple door at the bay.

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

10.0 out of 10, Exceptional, (55)
"Thank you so much for letting us stay at your house. The location was perfect for walking to restaurants and shops. Did a day at the wildlife refuge and spent some time on the beach. Plan to come back and enjoy another stay. "
The price is CA $158
CA $386 total
includes taxes & fees
Sep 29 - Sep 30
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

Waterfront Bungalow 2 on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

9.6 out of 10, Exceptional, (10)
"A perfect little get away with my husband and dogs! "
The price is CA $343
CA $438 total
includes taxes & fees
Sep 4 - Sep 5
Waterfront Bungalow 2 on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Cozy Barn Loft: Country Views & Central to Beaches

10.0 out of 10, Exceptional, (18)
"Loft was spotless, and had everything we needed. "
The price is CA $184
CA $363 total
includes taxes & fees
Sep 3 - Sep 4
Cozy Barn Loft: Country Views & Central to Beaches

The Neigh-Neigh - Location! Location! Location!

10.0 out of 10, Exceptional, (3)
"House was clean, cozy and convenient for our weekend stay on the island. We will be there for the same event next year and will consider booking The Neigh Neigh again depending on who comes next time! Cheers"
The price is CA $248
CA $695 total
includes taxes & fees
Sep 21 - Sep 22
The Neigh-Neigh - Location! Location! Location!

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

9.8 out of 10, Exceptional, (17)
"We stayed three nights and they were all delightful. The cabins are super clean, well equipped, comfortable beds, screened in front porch.- in other words anything you could wish! My only critique is that I don’t think the smoke alarm in the CO2 detectors were listed in the ad and they should be because they definitely are there!We will gladly come again someday."
The price is CA $343
CA $438 total
includes taxes & fees
Sep 4 - Sep 5
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Sweet cottage with outdoor shower

9.8 out of 10, Exceptional, (39)
"We enjoyed our week here. It was a perfect cottage for us. We enjoyed the screened in gazebo in the evenings and the convenient location."
The price is CA $248
CA $663 total
includes taxes & fees
Sep 3 - Sep 4
Sweet cottage with outdoor shower

The Blue Heron-Close to Beach & Large Screened Porch!

The price is CA $551
CA $964 total
includes taxes & fees
Sep 1 - Sep 2
The Blue Heron-Close to Beach & Large Screened Porch!

Nature's Retreat - Marsh & Wetland Views

The price is CA $482
CA $974 total
includes taxes & fees
Sep 22 - Sep 23
Nature's Retreat - Marsh & Wetland Views

Beechnut Villa-Waterfront-Cozy

8.0 out of 10, Very good, (1)
"House was lovely with fabulous views, but AC didn't work. The fans in the hallway told us that the owner knew they have an issue. Upstairs bedrooms were unbearable. Rental agency offered to move us, but the other properties didn't border the water or have of the lighthouse. Requested a discount and never heard back from them. "
The price is CA $551
CA $946 total
includes taxes & fees
Sep 13 - Sep 14
Beechnut Villa-Waterfront-Cozy

Sailor's Rest-Great In-Town Location!

9.0 out of 10, Wonderful, (2)
"I and my friends had a great stay at Sailor's Rest in Chincoteague, VA. It was the perfect place to relax, cook, and enjoy a long weekend. The house is within a short driving distance from everything (and you can walk too) and the beach is just 3 miles away. I would recommend for anyone wanting a weekend away in Chincoteague."
The price is CA $551
CA $1,053 total
includes taxes & fees
Sep 5 - Sep 6
Sailor's Rest-Great In-Town Location!

AlloWaves-Luxury Townhome w/ POOL & FISHING PIER

10.0 out of 10, Exceptional, (1)
"The house is spacious and beautiful. Perfect for a mini-getaway with a friend. We liked the open layout of the kitchen/living area. Bedrooms and bathrooms are spacious. Lovely sunset views within walking distance"
The price is CA $689
CA $1,150 total
includes taxes & fees
Aug 30 - Aug 31
AlloWaves-Luxury Townhome w/ POOL & FISHING PIER

Driftwood- Close to Beach!!

The price is CA $551
CA $884 total
includes taxes & fees
Sep 13 - Sep 14
Driftwood- Close to Beach!!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Deep Hole Hotel Reviews

Find out more about Deep Hole

Find out more about Deep Hole

Deep Hole Vacation Homes information

Number of reviews
168
Accommodation
632 Vacation Homes
Lowest Price
CA $158
Highest Price
CA $343

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