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Happy Pines by Seaside Vacations & Sales

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Located on a quiet street, you`ll love feeling as if you`re the only ones there.
Beautiful Happy Pines is the perfect home for your Chincoteague Island Vacation.
Happy Pines is the place to be on Chincoteague Island.
You`ll never want to leave the Screened-in Porch.
You`ll love the fabulous Backyard with Rooftop Deck and Screened-in Porch.

Reviews

9.8 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 8130.1 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Air-conditioning
  • Outdoor space
  • Fireplace

Explore the area

View map
Chincoteague Island, VA
  • Place, Robert N. Reed Downtown Waterfront Park
    ‪2 min drive‬
  • Place, Maui Jack's Waterpark
    ‪4 min drive‬
  • Place, Chincoteague National Wildlife Refuge
    ‪6 min drive‬
  • Airport, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
    ‪70 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Bedroom 1

2 Single Beds

Bedroom 2

1 Queen Bed

Bedroom 2

1 Queen Bed

Common Area

1 Queen Bed

2 bathrooms

Bathroom 1

Towels provided · Bathtub or shower

Bathroom 2

Towels provided · Bathtub or shower

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden
Dining area

About this property

Happy Pines by Seaside Vacations & Sales

Happy Pines - Refresh, Renew, & Reconnect

As you turn onto Pine Creek Drive, you will feel the hustle & bustle of the busy world melt away. Happy Pines is located near the end of this quiet street, nestled in a Pine Grove, and surrounded by beautiful trees and Beach Grasses. This lovely 3 Bedroom, 2 Bath Vacation Home is in THE perfect place - walking distance to the famous Carnival Grounds and everywhere you want to be, yet you will feel a million miles away. It is a wonderful combination of convenience and serenity. With a layout suitable for one family or two small families, this awesome home is definitely the place to be for your Chincoteague Island Vacation.

The warm and inviting Living Area with Gleaming Floors, Cozy Fireplace, Free WiFi, and huge Flat Screen Cable HDTV is a wonderful place to relax after a day of exploring the Beach and Assateague Island. Sink into the oversized, comfy furniture and share stories of the day's adventures and Wild Ponies. A wall of windows lets in glorious Natural Light and adds to the beauty of this Classic Home. Decorated with a Coastal Theme throughout, you will love the Local Art and pictures taken by the Owners themselves of their many beautiful Chincoteague Island memories.

Just around the corner, you will find Happy Pines has a large Dining Area that opens to the equally large Kitchen. There is seating for 6 at the Dining Table and 3 at the super-handy Breakfast Bar. The Kitchen is very well-stocked with all you need to make family meals a bay breeze. With rich Wood Cabinets, tons of Counter space, and every gadget you could possibly need, the Chef in your family will love cooking up some fresh Chincoteague Seafood here - or grilling some burgers on the Charcoal Grill! Not one to cook on vacation? No worries, you are a hop, skip, and jump away from many of our fabulous Local Restaurants. Just off the Dining Area is a spacious Screened-in Porch with comfortable furniture and Ceiling Fan overlooking the secluded Backyard. Just imagine relaxing here with your morning coffee and taking in that salty, sweet air. Wander upstairs to the Rooftop Deck and you will wonder why you never noticed how many stars really are in the sky.

Happy Pines has 3 Roomy Bedrooms and 2 Full Baths. The Master Bedroom, adorned in Nautical Navy and Sandy tones, has a Queen Bed and Flat Screen Cable TV. The Master Bath is delightful with Beachy Blue Walls, a large Walk-in Shower, and a window to let in those sea breezes and natural light. Bedroom 2 has a Queen Bed and is accented with colors of Fresh Lime and Navy Blue. Bedroom 3 features 2 Twins - a great room for the kids! A 2nd Full Bathroom with a Tub/Shower Combo is shared between these rooms. There is also a Queen Sleeper Sofa in the Living Area!

At Happy Pines, the Outdoor Living is as wonderful as the Indoor Living. The spacious and private Backyard is a great place to throw a Frisbee with the kids, play some Bocce Ball, or just chase Lightning Bugs. That is what this time is about, right? Relaxing, reconnecting, discovering, playing......ahhhh, the simple pleasures that are Chincoteague Island and Happy Pines.

Happy Pines - Relax. Unwind. Get in a Flip Flop state of mind.

Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. LINENS INCLUDED, NO SMOKING, NO VAPING, NO PETS. FAMILIES ONLY AND MUST BE AT LEAST 25.

Add dates for prices

Amenities

Kitchen
Washing machine
Air conditioning
Outdoor space
Fireplace

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
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

No pets allowed
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Smoking

Smoking is not permitted

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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property

About the area

Chincoteague

Chincoteague is home to this holiday home. The area's natural beauty can be seen at Chincoteague National Wildlife Refuge and Chesapeake Forest - Dunn Swamp Complex, while Museum of Chincoteague and Captain Timothy Hill House are cultural highlights. Maui Jack's Waterpark and Wallops Flight Facility are also worth visiting. Power boating, fishing and swimming offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
Map
Chincoteague Island, VA

What's nearby

  • Robert N. Reed Downtown Waterfront Park - 2 min drive - 1.4 km
  • Maui Jack's Waterpark - 4 min drive - 3.5 km
  • Chincoteague National Wildlife Refuge - 6 min drive - 4.8 km
  • Assateague Lighthouse - 9 min drive - 6.5 km
  • University of Maryland Eastern Shore - 55 min drive - 68.4 km

Getting around

  • Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional) - 66 min drive

Restaurants

  • ‪Island Creamery - ‬4 min drive
  • ‪Steamers - ‬3 min drive
  • ‪McDonald's - ‬6 min drive
  • ‪Teaguers - ‬4 min drive
  • ‪Famous Pizza & Sub Shoppe - ‬5 min drive

Frequently asked questions

Is Happy Pines is a delightful Chincoteague Island Vacation Rental in a private, se pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Happy Pines by Seaside Vacations & Sales?

As of 23 April 2026, prices found for a 1-night stay for 2 adults at Happy Pines by Seaside Vacations & Sales on 20 May 2026 start from NZ$317, 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.

What time is check-in at Happy Pines is a delightful Chincoteague Island Vacation Rental in a private, se?

Check-in begins at 4:00 PM.

What time is check-out at Happy Pines is a delightful Chincoteague Island Vacation Rental in a private, se?

Checkout is at 10:00 AM.

Where is Happy Pines is a delightful Chincoteague Island Vacation Rental in a private, se located?

Situated in Chincoteague, this holiday home is within 1 mile (2 km) of Robert N. Reed Downtown Waterfront Park and Chincoteague Channel. Maui Jack's Waterpark and Museum of Chincoteague are also within 3 miles (5 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 28 out of 33 reviews
Rating 8 - Good. 4 out of 33 reviews
Rating 6 - Okay. 1 out of 33 reviews
Rating 4 - Poor. 0 out of 33 reviews
Rating 2 - Terrible. 0 out of 33 reviews

9.6/10

Cleanliness

10/10

Check-in

9.8/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Gerta B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was nice and comfortable with all linens provided. The location is great - quiet spot, but you could walk to main street.
Stayed 2 nights in Aug 2025
Response from VrboOwner on 16 August 2025
Hi Gerta – thank you for your review! We’re so glad you enjoyed the comfort of Happy Pines and its quiet yet convenient location close to Main Street. We’d love to host you again anytime! – Julia
Verified

10/10 Excellent

Joelle M.

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

Wonderful vacation home!

Our family had a great time at Happy Pines! The house was spacious, clean, and comfortable with two incredible decks.
Stayed 7 nights in Aug 2023
Response from VrboOwner on 28 August 2023
So glad to hear your family enjoyed its stay, Joelle! We hope to have you all back soon!
Verified

10/10 Excellent

Pablo T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The place was very pleasant—quiet and free from any noise. I even had the chance to photograph a rocket launch from NASA Wallops. The house was wonderful, and everything worked out perfectly
Rocket from NASA Wallops from the backyard of the house
The moon from the backyard of the house
Deer in Wildlife Loop (very close)
Stayed 11 nights in Aug 2025
Response from VrboOwner on 25 August 2025
Thanks so much for choosing to stay with Seaside Vacations, Pablo! We're so glad you enjoyed your time at Happy Pines, and hope to have you back soon! Best, Tim
Verified

10/10 Excellent

Liz L.

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

Nice n private!!! Perfect location!

This is a lovely place to stay with family! Very nice n private! We will definitely come back again! It has a lovely screened in back porch!!
Stayed 3 nights in Sep 2022
Response from VrboOwner on 14 September 2022
Liz, WOW, thank you for the 5 Star review. We are happy you enjoyed the home and location. Yes, the screened porch is perfect. We hope you do come back and soon! Best, Lynn with Seaside Vacations
Verified

10/10 Excellent

Wanda T.

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

Super close

Our stay was absolutely wonderful. The property was clean, the check in process super easy and we were even notified that the property was ready and we could check in early. Communication from management was awesome. I definitely will book and stay with these guys again. Thanks for an awesome time away.
Stayed 2 nights in Jun 2025
Response from VrboOwner on 23 June 2025
We're so glad to hear you enjoyed your experience staying with Seaside Vacations, Wanda! Thanks for allowing us to be a small part of your island getaway. We hope to have you back soon! Best, Tim
Verified

10/10 Excellent

Kody M.

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

Family stay at Chincoteague

The house was perfect, tucked away on a small side street. Ideal for the children and super close to eveything we wanted to do. Would highly recommend to others and would galdly book again!]
Stayed 5 nights in Jul 2023
Response from VrboOwner on 8 August 2023
Thanks so much for choosing to stay with us, Kody! We hope to have you back soon!
Verified

10/10 Excellent

Traci J.

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

Fantastic house in a great location

Happy Pines is a nice home on a beautiful, quiet cul de sac. It is close to downtown and Chincoteague National Wildlife Refuge.
Stayed 2 nights in May 2022
Response from VrboOwner on 26 May 2022
Traci, So appreciate the 5 star review! We are glad you enjoyed the home and locations. Please visit us again! Best, Lynn with Seaside Vacations
Verified

10/10 Excellent

Patricia S.

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

Chincoteague for a few days

Stayed here with a friend for a few days. Quiet and peaceful neighborhood - just what was needed. House was just as advertised and rental company was great to work with. I would stay here again and again!
Stayed 3 nights in Jan 2023
Response from VrboOwner on 19 February 2023
Thanks so much for choosing to stay with us, Patricia! We're so glad you both enjoyed your stay, and hope to have you back soon! :)
Verified

10/10 Excellent

Stephen F.

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

Happy Pines lives up to its name

We loved our stay at the Happy Pines. It is tucked away at the end of a gravel road and provides solitude and opportunity to observe wildlife. There IS a microwave, even though it's not listed. We would definitely stay there again!
Stayed 7 nights in Aug 2023
Response from VrboOwner on 25 September 2023
Thanks so much for choosing to stay with us, Stephen! We're so glad you enjoyed your stay, and hope to have you back soon! :)
Verified

10/10 Excellent

Mike S.

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

Family trip

Everything went well. Easy to deal with. Great location. Great trip. Would return.
Stayed 4 nights in Jun 2019
Response from VrboOwner on 24 March 2020
Hi Mike! So happy to hear y'all will be returning! Repeat guests of Seaside Vacations get a discount! :)
Verified

10/10 Excellent

verna s.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was absolutely wonderful. Everyone enjoyed our trip and had a great time. It is definitely family friendly. We saw the deer out back. The screened porch was great and we used it all the time. The only thing I found to be not so good was the master bed. It needs a better mattress. But all in all we loved it and will be back some day. Thank you
Stayed 3 nights in Sep 2025
Response from VrboOwner on 10 September 2025
Thanks so much for choosing to stay with us, Verna. We're so glad to hear you enjoyed your time at Happy Pines! Mattresses can be pretty subjective, but we'll be sure to have our inspectors check it out to ensure that all is well with it. We can't wait to have you back! Best, Tim
Verified

10/10 Excellent

Scott G.

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

Great place to stay

This was the first time I have ever rented a house for a vacation and the experience was very positive. If I knew there were kayaks in the garage I would have stayed longer and enjoyed them too. It was a very positive experience.
Stayed 2 nights in Oct 2022
Response from VrboOwner on 10 October 2022
Thanks so much for choosing to stay with us, Scott! We're so glad to hear you enjoyed your visit, and hope to have you back soon! The kayaks will be waiting for you! :)
Verified

10/10 Excellent

Avi W.

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

Beach getaway

We needed to tread water for a week while moving across country. We enjoyed beach life, cycling and kick scooters around Chincoteague. Toms cove is a great sandy beach for boogie boarding.
Stayed 7 nights in Jul 2024
Response from VrboOwner on 10 August 2024
Thanks so much for choosing to stay with Seaside, Avi! We're so glad you enjoyed your stay at Happy Pines and hope to have you back soon!
Verified

10/10 Excellent

Stephen F.

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

These Pines are Indeed Happy

We can’t say enough good things about the Happy Pines. This is our second stay and it is clear that the owners are invested in the quality of the property. We only had to go out to the screened in porch to enjoy endless opportunities to observe wildlife. We will be back!
Stayed 7 nights in Jul 2024
Response from VrboOwner on 12 August 2024
We're so glad to hear you enjoyed your return to Happy Pines, Stephen! We're so glad you enjoyed your stay, and can't wait to have you back next year! :)
Verified

10/10 Excellent

Sue s.

Liked: Check-in, communication, location, listing accuracy

Nice place

very good location the only think it really wasnt very clean. But we left it clean. The house is nice my husband said he would like to buy it.
Stayed 7 nights in Jul 2023
Response from VrboOwner on 28 July 2023
We're so glad you enjoyed your stay, Sue and truly apologize for any cleaning concerns. We take great pride in that aspect of your process, and certainly wouldn't have minded sending someone back to touch up the home!
Verified

10/10 Excellent

W L.

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

Perfect island getaway

The house is located on a very quiet street, with lots of nature around. The screened-in porch and the deck above above make you want to spend more time at the property, but there is so much to do on the island and nearby - biking, hiking, kayaking. or just hanging out on the beach. And at the end of October, it feels like you get the island to yourself, while the weather is still nice.
Stayed 4 nights in Oct 2022
Response from VrboOwner on 11 November 2022
W L, Thank you so much for the 5 star review. We agree, we could hang out there 24/7. October is a great time here! Please visit us again and soon! Best, Lynn with Seaside Vacations!
Verified

10/10 Excellent

Erin W.

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

Perfect!

It was the perfect size for our party of 6. We loved the screened in porch and spent a lot of time in the evenings enjoying it. Nice, secluded, quiet location - a deer visited the yard! Very nice and clean
Stayed 3 nights in Oct 2018
Response from VrboOwner on 24 March 2020
Hi Erin! So happy you had a great time! :) Keep us in mind when planning your next beach vacation-- repeat guests at Seaside Vacations get a discount! :)
Verified

8/10 Good

Jeremy A.

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

Quick and Simple

The check in and checkout process was very easy and simple. No more waiting in line. Allows for more time with the family.
Stayed 7 nights in Jun 2022
Response from VrboOwner on 2 July 2022
Thanks so much for choosing to stay with us, Jeremy! We're so glad you enjoyed our express check in process, and hope to have you back soon!
Verified

10/10 Excellent

Lisa L.

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

Great Chincoteague beach house!

We were really happy with our short stay at Happy Pines. Great communication from the property manager and easy online check-in/check out. The house was pretty clean aside from a bit of sand on the floors and in the beds/sofas which seems to be par for the course for beach houses. Appliances seemed to all work though we didn't make use of all of them since it was a short stay. We really enjoyed the screened in porch and there was a double rainbow we were able to enjoy viewing from the rooftop deck the evening we checked in. We would definitely consider returning to Happy Pines in the future!
Stayed 2 nights in Aug 2024
Response from VrboOwner on 9 August 2024
Thanks so much for choosing to stay with Seaside Vacations, Lisa! We're so glad your family enjoyed its stay at Happy Pines, and hope to have you back soon! :)
Verified

8/10 Good

Michael S.

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

Happy Pine Stay

The house is very spacious and comfortable with a very nice screened in deck and the wildlife was entertaining in the yard. The house is in a very quiet section of town with no traffic. The only drawback was the bathroom which we thought the commode was very low and the type of shower door was a little inconvenient. Otherwise everything was great and we'll be back in the future.
Stayed 6 nights in May 2023
Response from VrboOwner on 24 June 2023
Michael, thank you so much, and hope to have y'all again!
Verified

8/10 Good

Dan & Laurie D.

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

Short vacay with Family

Property was as described., not fancy but comfortable. House is located on a private quiet street, but a little off the beaten path. You need to drive to get to stores and restaurants. Nice rooftop deck and screened patio. There was a slight mildew smell upon entering the property but seemed to go away once we aired it out. Ants traps were visible and accessible to our 2 year old (put them up high and out of his reach). Kitchen pans need to be replaced. Enjoyed our 2 night stay.
Stayed 2 nights in Apr 2023
Response from VrboOwner on 24 June 2023
I am glad you enjoyed your stay! I am happy to report that we have updated the cookware! So sorry about the ant traps - we would not leave those there, but it's possible a guest did. Thank you for staying with us.
Verified

6/10 Okay

abbey b.

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

Garage parking!

Check in & out was easy, property is semi private and very quiet. A much appreciated perk was parking in the attached garage to avoid loading and unloading the car in a cloud of mosquitoes each day! This rental is nice and clean but basic. It would benefit from upgrades such as more comfortable beds and couches. Bring your own pillows and blankets to make yourself at home! Overall, it’s a nice space and location, and the roof deck is great for star gazing on clear nights. We enjoyed the screened in porch even though it wasn’t totally mosquito proof :) The porch ceiling fan did not work during our stay, no big deal. Upon checkout, I relayed this to the management company and they said they’d resolve this. They were very responsive and communicative. We had no issues.
Stayed 7 nights in Aug 2022
Response from VrboOwner on 30 September 2022
Abbey, so glad you enjoyed the house! So sorry for the issue with the fan! Hope to have y'all again! Best, Elaine
Verified

10/10 Excellent

Jennifer B.

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

Star gazing deck!

A lovely week! Don't forget kitchen towels if you aren't renting linens.
Stayed 7 nights in Aug 2020
Response from VrboOwner on 21 August 2020
Hi Jennifer! So happy you enjoyed Happy Pines - and the location is great - close enough to everything but far enough away to enjoy quiet time! :) We hope to see you guys next year! Best, Lea Anna ~ Seaside Vacations
Verified

10/10 Excellent

Tim H.

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

Good place

Place was clean and little off the main road witch offered a little bit of a relaxed environment. Would stay again
Stayed 7 nights in Aug 2020
Response from VrboOwner on 18 August 2020
Hi Tim! We are so happy you enjoyed Happy Pines! It is off the beaten path which makes for a quiet vacation! :) We hope to see you and your family again next summer! Best, Lea Anna ~ Seaside Vacations
Verified

10/10 Excellent

Neeltje H.

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

Comfortable home in quiet neighborhood

This house is exactly as advertised -- comfortable, well-stocked, and in a very quiet neighborhood within an easy drive to every place we wanted to go. We enjoyed the big yard for outdoors and the ample air conditioning for indoors (it was a hot week when we were there)! All of my questions were answered very quickly and helpfully. And the Chincoteague wildlife refuge is just lovely!
Response from VrboOwner on 21 August 2020
Hi there! So very happy to hear you loved your stay at Happy Pines! It is a hidden gem! :) We hope to have y'all next year! Best, Lea Anna ~ Seaside Vacations

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