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1950's NAGS HEAD BEACH COTTAGE , IN EXCELLENT CONDITION840 sq ft 3 occp max

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Welcome to the Caddy Shack & the Beach! One of the best locations in Nags Head.
Property video
Living room w/ open floor plan into kitchen area ..
Retro lighting over sink area w/ dimmer switch .coffee maker .filters provided
Virtual fire “ looks real , sounds real “ Amazing ! Avail October- March

Reviews

10 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 378.0 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Rooms & beds

2 bedrooms (sleeps 3)

Bedroom 1

1 Queen Bed

Bedroom 2/ A Full Size Memory foam mattress

1 Double Bed

1 bathroom

Bathroom 1

Soap · Bathtub or shower · Toilet · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden
Dining area

About this property

1950's NAGS HEAD BEACH COTTAGE , IN EXCELLENT CONDITION840 sq ft 3 occp max

We are located in the heart of Nags Head, one of the best locations on the Outer Banks of North Carolina. Jim and I welcome guests who will enjoy a cottage that is in pristine condition. The cottage is in walking distance to the Bladen Street Beach Access (less then a (10 )ten minute walk or a two minute bike ride), we are between the highways which means you never have to cross the busy bypass to get to the beach! Take a stroll to the Nags Head Pier, Tortugas' Lie, and Lucky 12 Tavern or a bike ride to multiple art galleries, coffee shops, ice cream shops, and even Jockey's Ridge State Park (the largest dunes on the east coast which promise incredible sunsets). Kids and adults will enjoy a game of Putt Putt at Galaxy Golf. We pride ourselves in making sure the cottage is clean and well decorated. Adjoining the outdoor dining deck is a lounging deck which is a great place to lay out or read a book. We are less then nine miles to the town of Maneto and many Public Golf Courses.

Please feel free to call or email me. I am happy to guide you to all the cool local spots. Whether you are a couple, seniors, or a small family (3 occp max ) I can help you create a great vacation! Thank you for considering our cottage...Jim & Lisa Winn
PLEASE Note:: rates on vrbo are for 2 occp , cottage has a max occp of 3 .. extra rate will occur ..
IF YOU SEE THIS LISTING ON CRAIGSLIST, IT'S A SCAM. WE ONLY DEAL WITH VRBO AND HOMEAWAY.
* This cottage has 5 G wifi and provides a Streaming TV service…some buffering may occur *Ceiling height in all rooms are 6’8” with (1) door jam 5’11” … thats how most of the old nags head cottages where built in the 1950’s..We do allow pets (2 max ) 20.00per night (1 pet ) 25.00 per night (2 pet max ) ..
*PLEASE NOTE - TRAVEL INSURANCE IS HIGHLY RECOMMENDED.

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Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 23
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 2 total)
Fee of 20.00 nightly1pet,25.00 nightly 2 pet max
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Smoking

Smoking is not permitted
Not inside cottage
A 100.00 refundable security /damaged deposit will need to be paid at signing of rental/ pet agreement. Refund mailed 15 days after checkout...
pets are allowed sept 15 -may 25 ....please advise before requesting to book.. pet fee 20.00 per night (1 pet ) 30.00 per night (2 pet max )
There is no cleaning fee , but guest are required to leave cottage in very good order . If acceptable condition , security deposit will be refunded

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Nags Head

Located in Nags Head, this cottage is near theme parks and on the beach. Wright Brothers National Memorial and Monument to a Century of Flight are local landmarks, and some of the area's activities can be experienced at OBX Laser Tag and Destination Fun. Stop-N-Shop Beach Shop and Full Throttle Speedway are also worth visiting. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with hunting and hiking/biking trails nearby.
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Map
NAGS HEAD, NC

What's nearby

  • Jockey's Ridge State Park - 3 min walk - 0.3 km
  • Dowdy Park - 6 min walk - 0.5 km
  • beach - 9 min walk - 0.8 km
  • Tracks in the Sand - 17 min walk - 1.4 km
  • OBX Laser Tag - 3 min drive - 1.7 km

Getting around

  • Manteo, NC (MEO-Dare County Regional) - 18 min drive

Restaurants

  • ‪Biscuits N’ P*rn - ‬2 min drive
  • ‪Blue Moon Beach Grill - ‬3 min drive
  • ‪Poke Box - ‬2 min drive
  • ‪Mama Kwan's Tiki Bar & Grill - ‬3 min drive
  • ‪Single Fin Thai-Sushi Restaurant - ‬18 min walk

Frequently asked questions

Is 1950's NAGS HEAD BEACH COTTAGE , IN EXCELLENT CONDITION840 sq ft 3 occp max pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much does it cost to stay at 1950's NAGS HEAD BEACH COTTAGE , IN EXCELLENT CONDITION840 sq ft 3 occp max?

As of 1 Apr 2026, prices found for a 1-night stay for 2 adults at 1950's NAGS HEAD BEACH COTTAGE , IN EXCELLENT CONDITION840 sq ft 3 occp max on 7 June 2026 start from AU$358, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at 1950's NAGS HEAD BEACH COTTAGE , IN EXCELLENT CONDITION840 sq ft 3 occp max?

On-site parking is available at the property.

What time is check-in at 1950's NAGS HEAD BEACH COTTAGE , IN EXCELLENT CONDITION840 sq ft 3 occp max?

Check-in begins at 4:00 PM.

What time is check-out at 1950's NAGS HEAD BEACH COTTAGE , IN EXCELLENT CONDITION840 sq ft 3 occp max?

Checkout is at 10:00 AM.

Where is 1950's NAGS HEAD BEACH COTTAGE , IN EXCELLENT CONDITION840 sq ft 3 occp max located?

Situated on the beach, this cottage is within a 10-minute walk of Dowdy Park and Outer Banks Beaches. Nags Head Fishing Pier and Jockey's Ridge State Park are also within 15 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 182 out of 198 reviews
Rating 8 - Good. 13 out of 198 reviews
Rating 6 - Okay. 3 out of 198 reviews
Rating 4 - Poor. 0 out of 198 reviews
Rating 2 - Terrible. 0 out of 198 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.4/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Cindy S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We absolutely loved the property. It was cozy and quaint and very beautifully done as far as furnishings and amenities.
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Greg&Carey U.

Liked: Cleanliness, check-in, communication, location, listing accuracy
My wife and I had a wonderful stay in this 1950s cottage. Spectacular host, perfect for pets and fully equipped for your in home experiences.
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Charlene A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Caddy Shack had everything we needed and was definitely pet friendly. Many “little touches” added to its charm. Would certainly return.
Stayed 6 nights in Mar 2026
Verified

10/10 Excellent

edward a.

Liked: Cleanliness, check-in, communication, location, listing accuracy
EVERYTHING WAS GOOD WE REALLY ENJOYED THE BEACH HOUSE IT WAS CLEAN AND VERY NICE DECOUR JIM WAS GREAT WE WOULD DEFFINENTLY BOOK THIS HOUSE AGAIN
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Elissa W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was welcoming and offered tips and recommendations on things to do, place to eat, etc. The accommodations were lovely, it’s a very relaxing and enjoyable spot with the cutest back yard for you and your family/fur baby.
Fireplace Lights
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Megan B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Exactly as described…cute little cottage with a little fenced yard that’s a short walk from the beach. It was the perfect launch point for us to visit all areas of the Outer Banks.
Stayed 6 nights in Aug 2025
Verified

10/10 Excellent

Tammy D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Jim was very welcoming. Listing was exactly as described.
Stayed 2 nights in Dec 2025
Verified

10/10 Excellent

laurel b.

Liked: Cleanliness, check-in, communication, listing accuracy
Excellent dog area. Private patio. Adorable cottage. Clean. Awesome host.
Stayed 8 nights in Sep 2025
Verified

10/10 Excellent

Marilyn S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cozy and very comfortable. The perfect little beach house!
Stayed 6 nights in Jun 2025
Verified

10/10 Excellent

Douglas C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was in good shape. It is on a busy highway, but the noise lessened in the evening. Kitchen appliances worked well. Host was readily available with questions.
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Diane H.

Liked: Cleanliness, check-in, communication, listing accuracy

Cottage for short people

Cute little comfy cottage
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Christie C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house is very clean and has everything you need. It is in a great location that is central to everything you might want to do. Jim is great at communicating and is very helpful with suggestions on places to eat and things to do. We would definitely rent this house again!
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

Kevin B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Good Time in Nags Head

Very pleasant cottage and owner
Stayed 3 nights in Mar 2024
Verified

10/10 Excellent

Jen P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cute, clean and comfortable place to stay. Walk to the beach in only 9 minutes by taking the "secret route" ! Outdoor shower great place to rinse the sand off after a day at the beach Convenient location to explore the rest of OBX.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

LILLIAN B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Anniversary stay

Impressive, clean & cozy cottage with good rates and excellent host. Will definitely be back@
Stayed 2 nights in Nov 2024
Verified

10/10 Excellent

Linda D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent place

Great place and the host was very hospitable and when we had a problem he was right on it. Looking forward to book the house again .
Stayed 3 nights in Mar 2025
Verified

10/10 Excellent

Parker M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful cottage!!

We had a great stay. The cottage was so nice, clean, clutter free and had everything we needed. The yard for the dogs was great. Thanks for a wonderful stay!
Stayed 5 nights in Jun 2024
Verified

10/10 Excellent

Tina G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Home Away From Home

Such a cozy little 1950's style home in just the right location. Just a few minutes drive and you are at the shops, restaurants and so much more. We will definitely stay here again.
Stayed 3 nights in Apr 2024
Verified

10/10 Excellent

laura c.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beach Cottage

We really enjoyed staying at the Caddyshack! It was cozy, comfortable, and very clean. A short walk from the beach and the perfect getaway!
Stayed 2 nights in Feb 2023
Verified

10/10 Excellent

Ronald B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Stay

Awesome quaint cottage
Stayed 2 nights in Jan 2025
Verified

10/10 Excellent

deanna r m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Rainy

Very cute, comfortable beachy cottage. Good location from shops, restaurants, beaches and other sites.
Stayed 2 nights in Apr 2024
Verified

10/10 Excellent

Ashley M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Stay in Nags Head

Loved staying at the Caddy Shack in Nags Head! Jim was incredibly attentive. The cottage is in a great condition and in a great location-- close to beach access and restaurants. Would love to stay here again!
Stayed 3 nights in Nov 2023
Verified

10/10 Excellent

Frank O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent! Definitely Coming Back Again!

The first day we arrived, the owner greeted us and made sure we had evening we needed for our stay. He even told us about local events. The house, even though directly on the road, isn't far from the beach nor far from local restaurants, shops, and other activities. I'll definitely be going back here again!
Stayed 6 nights in Jun 2025
Verified

10/10 Excellent

kitty b.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great time in Nags Head

Our stay was terrific. The place was exactly as advertised. Our host was amenable and easy to communicate with. He met us onsite for checkin and offered places nearby for meals. We couldn’t have asked for more.
Stayed 4 nights in Oct 2024
Verified

10/10 Excellent

Michele C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing trip!

Thank you Jim for a fabulous week at Caddyshack. We had the best time and enjoyed the accommodations and recommendations. Highly recommend!!!!
Stayed 6 nights in Aug 2023

About the host

Hosted by James Winn

Host profile image
Welcome to our piece of paradise, we take great pride in providing our guests with comfortable & clean accommodations. We are detailed oriented, always reflecting on how we can make the cottage a unique experience for our guests. We care about making sure it is clean and comfortable.

Why they chose this property

Pet Friendly( pet rate 25.00 per night 1 pet & 30.00 per night 2 pet max . Has a beautiful fenced in back yard with plants, shrubs and flowers. Bose surround sound system, linked to the DVD for movie goers. One of the coolest outside showers in the OBX. Centrally located making it easy to visit many landmark places without driving long distances. Easy access to multiple top Grocery Store's if you choose to dine in. We also do a monthly barrier mosquito spraying that greatly reduces the biting pest ... so you can enjoy the outside ... it works

What makes this property unique

Owners of Sky Blue, a new 2.5bedroom cottage. Check us out at #4176009 if this property is not available. We also do a monthly barrier MOSQUITO spraying to greatly reduce those biting pest ...IT WORKS ... now you can enjoy the deck / yard and grilling

Languages:

English

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They consistently provide great experiences for their guests
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