Entire home

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

Beachfront cottage with kitchen and patio

Welcome to the Caddy Shack & the Beach! One of the best locations in Nags Head.

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

You will be comfortable in our living room /streaming TV/movies/surround sound)

Overview
Amenities
Policies
Location

Exceptional

2 bedrooms1 bathroomSleeps 3840 sq ft

Popular amenities

Dryer
Washer
Fireplace
Kitchen

Explore the area

NAGS HEAD, NC

Place, Jockey's Ridge State Park
‪7 min walk‬
Place, Nags Head Fishing Pier
‪1 min drive‬
Place, Jennette's Pier
‪10 min drive‬
Airport, Manteo, NC (MEO-Dare County Regional)
‪23 min drive‬

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.

Add dates for prices

Amenities

Kitchen

Washing machine

Dryer

Pet-friendly

Free WiFi

Air conditioning

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Kitchen
Washer
Dryer
Pet-friendly

House Rules

Check in after 4:00 PM

Minimum age to rent: 23

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed: dogs (limit 2 total)

Fee of 20.00 nightly1pet,25.00 nightly 2 pet max

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. Seaside Art Gallery and Wright Brothers National Memorial are cultural highlights, and travellers looking to shop may want to visit Outer Banks Mall and Outlets Nags Head. Travelling with kids? Consider Destination Fun and Stop-N-Shop Beach Shop. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with cycling and hunting.

View more Cottages in Nags Head

NAGS HEAD, NC

What's nearby

Jockey's Ridge State Park - 7 min walk - 0.7 km
Nags Head Fishing Pier - 1 min drive - 0.4 km
OBX Laser Tag - 2 min drive - 2.0 km
Nags Head Woods Preserve - 6 min drive - 5.0 km
Jennette's Pier - 10 min drive - 10.6 km

Getting around

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

Restaurants

‪Biscuits N’ P*rn - ‬2 min drive
‪Dirty Dick's Crab House - ‬2 min drive
‪The Kill Devil Grill - ‬3 min drive
‪Mulligan's Grille in Historic Cottage Row - ‬13 min walk
‪Morning View Coffee Company - ‬13 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).

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?

This family-friendly Nags Head cottage is located on the beach, within a 10-minute walk of Dowdy Park and Outer Banks Beaches. Jockey's Ridge State Park and Tracks in the Sand are also within 15 minutes.

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.4/10

Location

9.8/10

Listing accuracy

10/10 Excellent

Christie C.

6 Sept, 2025

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

10/10 Excellent

Diane H.

21 Jun, 2025

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

Cottage for short people

Cute little comfy cottage

Stayed 7 nights in Jun 2025

10/10 Excellent

Kevin B.

9 Apr, 2024

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

Good Time in Nags Head

Very pleasant cottage and owner

Stayed 3 nights in Mar 2024

10/10 Excellent

Linda D.

9 Mar, 2025

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

10/10 Excellent

LILLIAN B.

25 Nov, 2024

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

10/10 Excellent

Parker M.

1 Jul, 2024

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

10/10 Excellent

Ronald B.

9 Jan, 2025

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

Stay

Awesome quaint cottage

Stayed 2 nights in Jan 2025

10/10 Excellent

David N.

1 May, 2024

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

Just Perfect

I can't say enough about the place we booked the Owner was super nice the cottage was just perfect and it was just walking distance to the Beach if we decide to vacation at Nags Head again this will be the place we will book.

Stayed 4 nights in Apr 2024

10/10 Excellent

Bryan G., Goochland, VA

17 Feb, 2024

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

Valentines Getaway 2024

We absolutely loved your adorable cottage. It was just perfect in every way. Great spot to stay in Nags Head, and the weather was great. The decor was so perfect for the cottage. Hopefully, you will allow us to stay again when we return to Nags Head.

Stayed 2 nights in Feb 2024

10/10 Excellent

Mark L., Burnsville

21 Oct, 2023

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

Great stay

Our host Jim was very accommodating and helpful. Cottage was perfect size for my wife and my little Frankie(rat terrier) and was centrally located to KDH, Kitty Hawk and Corolla were easy to get to . Great place to relax or visit nearby attractions. We will be back

Stayed 7 nights in Oct 2023

10/10 Excellent

Patrick M.

25 Jun, 2023

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

Great place to stay

Great location to enjoy the beach, shopping and restaurants. Quick walk to the beach. The deck was a great place to hang in the evenings to relax. The yard was a great size for our dogs. Jim, the owner, was great in communicating with us before getting there as well as during out trip. Would highly recommend this place!

Stayed 5 nights in Jun 2023

10/10 Excellent

Jane D.

3 Jun, 2024

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

Beach Cottage

The cottage meet all our needs. Short walk to the beach, fenced in lawn for our dog. It was decorated beautiful and very comfortable. Very clean.

Stayed 7 nights in May 2024

10/10 Excellent

Angela M.

24 Jan, 2019

Perfect!

This was a perfect vacation rental! House was clean and well stocked with essentials. The location was close to the beach and near many attractions and restaurants. The host was very friendly and accommodating. I would not hesitate to stay again!!!

Stayed 2 nights in Jan 2019

10/10 Excellent

Lona G.

9 Oct, 2023

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

Charming, Cozy Cottage

This little cottage was perfect for our weekend down to Nags Head for a wedding. Super cute and cozy cottage with a nice little vibe. Very quiet, clean as a whistle, with an adorable fenced backyard which our little Papillon enjoyed. The owner met us for check in and was very friendly and personable. We very much enjoyed our stay and would absolutely stay in this beautiful little cottage again!

Stayed 2 nights in Oct 2023

10/10 Excellent

Jeff M.

5 Oct, 2023

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

Great central location and host

Nice clean cottage within walking distance of beach access. Location was also central to the outer banks offering driving access to many great sights, restaurants, and activities. Jim was great from the start and everything was as advertised. We were greeted at check in to the cottage and had personalized service uncommon to many rentals. Would definitely recommend for a future stay.

Stayed 5 nights in Sep 2023

10/10 Excellent

Amanda P.

13 Aug, 2023

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

Convenient location, clean cosy cottage

Jim’s cottage is conveniently located, a short 5mins walk to the beach, few mins drive to nearby food lion and the Jockey Ridge’s Park. The cottage is clean and well-equipped. A nice outdoor area with bbq. Jim is very helpful and great in communication. Great place for small group.

Stayed 5 nights in Aug 2023

10/10 Excellent

Dawn T., Stafford, VA

31 May, 2023

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

Loved the Caddy Shack

Cute home with all the amenities you'd need for a get away. Very clean, nice deck for eating or hanging out. Jim was an excellent host, very nice, easy to contact. He left us a list of recommendations for restaurants and golfing.

Stayed 4 nights in May 2023

10/10 Excellent

Marianne J.

6 Mar, 2023

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

Winter getaway

The time spent at this property gave us and my pups a much-needed time away from our home up North. The cottage is adorable and well-kept and Jim, our host, was just a phone call away for anything we might need. The pups and us spent hours enjoying the deck and fenced-in yard. I wholeheartedly give this listing a five-star rating.

Stayed 11 nights in Feb 2023

10/10 Excellent

Alecia Diane S.

17 Sept, 2024

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

The Caddy Shack

My friends, dog and I enjoyed the cottage very much. It was so relaxing and you knew you were at the beach by how nicely the place was decorated. My favorite thing was showering under the stars, my dog’s was, of course, the nice back yard, and my friends loved how quaint the place was. The owners could not have been any nicer and accommodating. Despite the busy location of the cottage, I would still book again next year.

Stayed 4 nights in Sep 2024

10/10 Excellent

maria c.

8 Jan, 2024

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

OBX Gem

We loved our stay at the cottage. Perfect location. Very clean. Beautifully decorated. Had everything we needed. Nice short walk to beach. Felt like a private spot. Owners really take care of the cottage. Took our pup. Fenced in back yard a bonus. Great correspondence with owners. We would most certainly stay again.

Stayed 2 nights in Jan 2024

10/10 Excellent

Susan c.

28 Mar, 2024

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

Comfy Cottage

The cottage was exactly as described. Cozy, clean, well equipped and maintained, convenient location, with a short walk to the beach. The fenced in backyard was perfect for our two small dogs.The owner was very attentive and helpful in orienting us to the area. We did not experience the best weather conditions so it was wonderful to have a comfortable home away from home to return to in the evening. I would consider returning in the future.

Stayed 3 nights in Mar 2024

10/10 Excellent

Elissa W.

30 Oct, 2025

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.

Stayed 4 nights in Oct 2025

10/10 Excellent

Mark Y.

28 Oct, 2025

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

Very clean property. We truly enjoyed our stay even though the weather was not very cooperative. Jasper (our golden) enjoyed the back yard and his walks on the beach when it wasn’t raining. Definitely will be back. Proximity to great restaurants was also a plus. Jim thank you for allowing us to stay in your home!!!

Stayed 5 nights in Oct 2025

10/10 Excellent

laurel b.

4 Oct, 2025

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

Excellent dog area. Private patio. Adorable cottage. Clean. Awesome host.

Stayed 8 nights in Sep 2025

10/10 Excellent

Megan B.

18 Sept, 2025

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

About the host

Hosted by James Winn

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