Cottage vacation rentals in Chincoteague

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Popular amenities for Chincoteague cottage rentals

Cottage rentals with free parking

Guest favorite
Cottage in Onancock
5 out of 5 average rating, 44 reviews

Sea Glass Cottage - The best relaxation vacation.

CherylRating, 5 stars3 months ago
Sea Glass Cottage was a delight! The house was very clean, bright and totally charming! Doris has everything you could need for a couple nights or extended stay. I would suggest everyone who stays read her "Welcome" book. She has great suggestions for dining, sightseeing, art galleries, etc. Beds are comfortable and the bathroom is VERY large. Onancock is a fun, charming town to visit. We will definitely return and, if Doris will have us, we'll be staying at Sea Glass Cottage. Thanks Doris for a great visit! Cheryl and Jerry
Guest favorite
Cottage in Berlin
4.93 out of 5 average rating, 92 reviews

Quiet Retreat near Assateague Island

DeniseRating, 5 stars8 months ago
This was our second trip to Catherine's retreat and we loved our stay this time even more than our first. Both Catherine and her husband assisted us when we had questions and provided suggestions for local events. The property is such a restful delight; from the pool, the views of the marshes, the quiet, and the plethora of wildlife to see. The home is comfy and we had everything we needed to make ourselves great meals and just soothe the soul. Between spending time on Assateague by day and returning to this special place at night, we came home restored. Thanks again!
Top guest favorite
Cottage in Onancock
5 out of 5 average rating, 52 reviews

Waterfront Victorian home in downtown Onancock

NazaninRating, 5 stars2 weeks ago
We enjoyed our stay. The house had all the comforts of home with a well stocked kitchen. The bed was comfortable. We are looking forward to coming back.
Top guest favorite
Cottage in Smith Island
5 out of 5 average rating, 51 reviews

IDLEHOUR, 3 BEDROOMS 2 BATHS W/ DOCK

MelissaRating, 5 stars7 months ago
This was our 2nd stay on the island , but first time at Mary Kim's. Great hospitality including home cooked egg rolls that made the long journey even more worth it. The only downfall would be the dock and kayak spot is a couple doors down, but Mary Kim was very communicative. lastly, I highly recommend the golf cart service on the island, gives you more of an ability to explore the island.
Top guest favorite
Cottage in East New Market
4.95 out of 5 average rating, 64 reviews

Cottage on Cabin Creek

MicheleRating, 5 stars1 month ago
It was a great stay. Host was responsive and home was calm and clean. Loved seeing the osprey from bed! Those windows highlighted the beautiful view. The weather was a bit dumpy but the space provided everything we needed.
Guest favorite
Cottage in Reedville
4.89 out of 5 average rating, 46 reviews

Waterfront Bay Cottage w/ Your Own Private Beach

BrandonRating, 5 stars2 weeks ago
We had a fantastic stay at this charming cottage on a private beach! The peaceful setting and direct access to the water made for a truly relaxing getaway. We especially loved the Adirondack chairs and firepit overlooking the Chesapeake Bay—perfect for amazing views and cozy evenings. The master bedroom and living spaces offered beautiful water views that made every moment feel serene and special. The owner was incredibly accommodating with check-in and shared thoughtful, personal tips that made our stay even more enjoyable. Highly recommend this spot for anyone looking to unwind by the bay!
Guest favorite
Cottage in Gwynn's Island
4.91 out of 5 average rating, 34 reviews

Little Gray Beach House

CorrineRating, 5 stars1 week ago
We loved our short stay at the Little Gray House. The view alone was worth the stay. The beaches are both easy walks and the area is lovely. Everything was clean and cozy and Bronwyn and Kat gave lots of information ahead of time, including some great recommendations. Would definitely recommend checking out The Hatchery and the Gwynn’s Island Museum on the island and spending some time exploring Mathews. We will be staying here again and hopefully soon!
Guest favorite
Cottage in Topping
4.97 out of 5 average rating, 62 reviews

The Little Blue Cottage - Topping : Waterfront!

MaryRating, 5 stars1 month ago
Perfect vacation getaway! I was so impressed with TLBCT! Forrest and Mariah provided total transparency in their advertising of The Little Blue Cottage at Topping. Everything was just as they listed and ALL on one floor. But it was the little extra touches that did it for me, the noise machines at each bedside, (which I now have to get one since returning home), the caring way that they communicated with me before, during and after the trip, and the endless supply of conveniences in case you forgot something! With elderly parents, we cooked all meals at the home, and the kitchen was well stocked to make that happen! I think I have found my home away from home. I can’t wait to return to the peaceful TLBCT. Thank you for sharing your beautiful and amazing home with me, my husband, my grown son, two grandmothers and our fur babies. We will be back!!❤️

Cottage rentals with a hot tub

Guest favorite
Cottage in Bethany Beach
4.94 out of 5 average rating, 17 reviews

Bethany Beach Sea Colony Canalside Sleeps 7

JosephRating, 5 stars3 months ago
We enjoyed Kristen’s home it was so he perfect location for our itinerary on this adventure. Blessings - joe and Jen
Top guest favorite
Cottage in Dewey Beach
4.89 out of 5 average rating, 80 reviews

Uncle Buck's

BreezyRating, 5 stars3 weeks ago
My friend and I loved staying at this little house. It was so close to the beach, the hot tub was amazing in the evenings and the house was comfortable and welcoming. It was clean, organized and well stocked with the towels. Great little getaway spot at a wonderful price.
Top guest favorite
Cottage in Woolford
5 out of 5 average rating, 64 reviews

Waterfront Cottage, Pier, Sunsets, Hot Tub,Kayaks

TheresaRating, 5 stars1 day ago
Natalie was a wonderful host - the cottage was clean and welcoming and looked just like the photos. Natalie was very responsive, flexible and friendly. The river was peaceful and we enjoyed kayaking and fishing off the dock. We are very thankful we found such a perfect spot for our weekend trip to Maryland.
Guest favorite
Cottage in Marion Station
4.7 out of 5 average rating, 37 reviews

Year Round Playground - Rare Rustic-Modern Getaway

JaniceRating, 5 stars9 months ago
The house was very clean and very fresh smelling. Being in the woods surrounded by trees you can sometimes expect a musty smell, but that was not the case at all. The house was immaculate, and the rooms were very comfortable. The house was very quiet and private and the room was a nice touch. We all enjoyed the pool table. My husband did a lot of fishing at the dock and we also enjoyed the pool and the hot tub. We will definitely come back and stay at this house. Nadia was a great host. She mentioned that they are just starting out being a airbnb host, but you wouldn’t know it. The house had everything we needed.
Guest favorite
Cottage in Rehoboth Beach
4.95 out of 5 average rating, 172 reviews

Dog friendly *HOT TUB* Close to outlets, Sleeps 7

BeatriceRating, 5 starstoday
This was our second time staying at JoJo’s cottage and it was another amazing experience! The house really makes you feel like you’re right at home. The kitchen is well stocked, so we were able to do a lot of cooking at the house. But you’re also so close to so many restaurants for when you’re feeling something easier! It really is a perfect spot, especially if you have dogs and/or kiddos. We would totally book again next summer 😊
Guest favorite
Cottage in Reedville
4.9 out of 5 average rating, 205 reviews

Bay cottage 🏖on the beach. Stunning views🏝

PaulRating, 5 stars1 week ago
We LOVED our stay! The screened porch overlooking the beach was so peaceful and our favorite place to be in the evening. The house was lovely, well cared for, very clean, and very tastefully decorated. The welcome book provided everything you needed to know about the house and surrounding area. We will be back again!
Guest favorite
Cottage in Lusby
4.91 out of 5 average rating, 43 reviews

Hot Tub Hideaway by Shark Tooth Shores

RebeccaRating, 5 stars3 weeks ago
Surrounded by trees and the sound of waves- perfect place to relax & unwind. Quick but steep hike to the secret beach. Cool spot and more shell than I expected. Kyli was a responsive host, answered all my questions. Also, recommended Island Hideaway for dinner and it was amazing. Homemade pasta and desserts made in house daily. Great views and delicious foods & drinks.
Superhost
Cottage in Scotland
4.85 out of 5 average rating, 20 reviews

Hays Beach House - Hot Tub - Private Beach

DelaneyRating, 5 stars3 months ago
Hays Beach House was the perfect home base for my group of 10 sailors. We were able to comfortably sleep, relax in the hot tub, and cook enough to feed a small army. The beds are comfy, the kitchen is well stocked, and the sunrises here are stunning. Tim is a friendly and helpful host and overall the experience was nothing but pleasant.

Pet-friendly cottage rentals

Guest favorite
Cottage in Melfa
5 out of 5 average rating, 15 reviews

Whitsapenny Cottage at Vaux Hall Farm

WalterRating, 5 stars2 weeks ago
Would return and recommend to others. Beautiful pristine space with numerous areas for guest to spread out and experience the beauty of the area and learn about the history and renovation of that particular farm and community. Very interesting restoration of existing structures and addition of many more places and ways to learn about and enjoy the natural surroundings.
Superhost
Cottage in Chincoteague
4.72 out of 5 average rating, 99 reviews

SNUG HARBOR waterfront cottage with a grand view!

AlexandraRating, 5 stars1 week ago
We ABSOLUTELY loved our visit, and plan to return and stay with Basia! Our weekend consisted of rainy weather and she offered us a covered porch which was well worth it!! Each morning we had a peaceful water view with the horses in the distance. I don’t think it could get any better. The boat tour was SO much fun. Basia stayed in contact with us about when would be the better time to go. She really looked out for us when the weather would be at its peak. Her recommendations never failed to impress. Thank you SO much for having us!! We plan to be back.
Guest favorite
Cottage in Deltaville
4.83 out of 5 average rating, 180 reviews

The Little House at Waveland

AshleyRating, 5 stars3 days ago
We had a great time at Diana’s place. The water access was awesome and we had lots of fun with the kayaks. We were able to walk through a wooded trail to a nearby restaurant which was so nice. The location felt private and naturally beautiful while being not far from grocery stores and restaurants. Diana’s neighborhood is beautiful and the space is charming and comfortable. Such a fun way to see the Chesapeake, we would love to come back!
Top guest favorite
Cottage in Frankford
4.99 out of 5 average rating, 160 reviews

19th Century Coastal Cottage with Modern Amenities

AllyRating, 5 stars1 week ago
Such a cute place to stay! It’s very quaint and super well decorated. Is as shown in pictures! Great location for beaches!
Superhost
Cottage in Painter
4.89 out of 5 average rating, 93 reviews

Cottage by the bay (private peaceful surroundings)

JorgeRating, 5 stars5 days ago
Very secluded but I don't mind that all. The home is beautiful and the host is very attentive.
Superhost
Cottage in Dewey Beach
4.89 out of 5 average rating, 203 reviews

Quaint Beach Block Cottage, 100 steps to the beach

MariaRating, 5 stars1 month ago
We loved staying at 14 Carolina Street! The house was great and was a very short walk to the ocean! Kelly and Thomas were very responsive and friendly! This home was a great location, would definitely come back again!
Top guest favorite
Cottage in Lusby
4.98 out of 5 average rating, 276 reviews

Gettin to the point. ( Cove Point Beach)

AlisRating, 5 stars3 weeks ago
Lisa was very responsive to all my texts as I had several personal hiccups trying to get on my trip. Her cottage is absolutely adorable and I am eager to come for a second visit. The cottage is very comfortable with a variety of indoor and outdoor space to gather in. In addition, it is in a great location with the beach just across the street. The neighborhood was peaceful and a sweet beach community. The fenced in yard was a gem as I was traveling with a dog.
Guest favorite
Cottage in Exmore
4.95 out of 5 average rating, 41 reviews

Waterfront Sunsets | Pet-Friendly Escape | No Fees

NeethiRating, 5 stars1 month ago
There is no better place for a relaxing time away with family (including dogs!). The hosts have taken such care to ensure that every need is taken care of and even added little touches to make the experience extra special. We had originally planned to explore more of the eastern shore, but we could barely get ourselves to leave the awesome property. Nothing prepared me to see such a great sunset on the western horizon from the east coast! What a delight! Most of all, and most importantly for us, the home was truly dog inclusive. We brought our two large dogs with us and the hosts had prepared for it all - covers on furniture, dog bowls at the ready, even dog towels and shampoo! We had an absolute blast at the little beach area and on the dock, but definitely do watch out and follow the host’s instructions to stay safe from the sharp rocks and steep dock stairs. The home is easy to care for with no unreasonable expectations from the host (like in some airbnbs). Check in and relax!

Quick stats about cottage rentals in Chincoteague

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    2.3K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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