Holiday houses in Chincoteague Bay

4.99 out of 5 average rating, 265 reviews

Farm stay in Onancock

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

4.97 out of 5 average rating, 583 reviews

Apartment in Greenwood

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

Superhost

Houseboat in Snow Hill

4.87 out of 5 average rating, 130 reviews

"Jolly"- Houseboat Getaway

#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

4.92 out of 5 average rating, 230 reviews

Sun, Sand & Sea | Your Cozy Oceanfront Hideaway

**2025 guests: Our pool and hot tub are in the process of being renovated and will be closed during your stay. This does not impact our condo, but you will not be able to use these amenities.** -Oceanfront -Indoor pool & Hot tub -Walk to local dining and shopping -Elevator accessible plus luggage carts -Full kitchen for cooking meals -Fast Wifi and Streaming TVs -Fully Stocked Home: Clean linens, towels, toilet paper, paper towels & more!

5 out of 5 average rating, 103 reviews

Loft in Hebron

Waterfront Barn Loft with Modern Cabin Vibe

Relax in nature for a while in our beautiful and cozy barn loft. The loft is located next to our primary residence on 7 private acres along scenic Rewastico Creek, offering year round beauty. Kayak on, or relax by, the tidal marsh creek which is fed by the Nanticoke River and Chesapeake Bay. Centrally located between popular Eastern Shore destinations such as Atlantic beaches and historic small towns. A serene oasis with abundant wildlife.

Guest suite in Chincoteague

4.94 out of 5 average rating, 316 reviews

Baywatch North-Waterfront & Roaming Ponies

Lovely space! 2 queen bdrm unit decorated with coastal charm, each with a door to the outside. Make-shift kitchen with microwave, small fridge, stoked Keuring coffee and tea bar, shared patio cooking area, bbq grill, fantastic view, beach items, plenty of parking, very quiet, out of the way of everything, super laid back host living in the other portion of the house. There is no living room. Labradors and cats on premises, ponies too!

Apartment in Chincoteague

4.86 out of 5 average rating, 189 reviews

Sunset Haven Downtown

Broadband WIFI newly installed and dependable! This special place is located in the heart of historic downtown Chincoteague above a wine shop/jewelry boutique. Your backyard is a waterfront park with our famous Love Chairs! Watch the sunset from your waterfront window or deck. Walk to shopping, restaurants, and more! An apartment with old time charm and new polished adds to feel as modern as needed! Onsite Laundry- Linens provided

4.98 out of 5 average rating, 281 reviews

Tiny home in Selbyville

Destination Location! Farm Animals, Tours, Beaches

✨Scratch tiny house living off your bucket list!✨ Wake up to the cheerful sounds of barnyard animals that surround this unique tiny house escape! The "Garden Hideaway" is thoughtfully curated to inspire joy and help you reconnect with the simpler things in life. Just a few minutes from the beach, this tiny home comfortably sleeps two (2) guests, with an option to add a third (3) for a small fee.

4.93 out of 5 average rating, 114 reviews

Oceanfront 2 Bedroom-Sleeps 6-Indoor/Outdoor Pool

Kick back and relax in this beautiful and modern newly remodeled condo in Golden Sands! This rare 2 bedroom, 1.5 bathroom unit has an amazing Master Suite with full-length windows providing panoramic views down the coastline, and direct access to the private patio. Renowned building amenities include outdoor pool, top floor indoor pool, gym, tiki bar, sun deck & more. Linens & towels included!

Guest suite in Machipongo

5 out of 5 average rating, 107 reviews

Peaceful Suite in Machipongo

Welcome to our soul-nourishing space perfect for your getaway! A magical place where time seems to stand still in the peace and tranquility. Nature beckons as birds fly back and forth, chimes sing in the breeze, stars glisten in the sky. Welcome to Feather Tree Retreat, a refreshing haven on the Eastern Shore of Virginia!

4.92 out of 5 average rating, 429 reviews

Apartment in Ocean City

Private suite .5 mile from beach/no shared spaces

This spacious, private master suite is perfectly located on 116th street, half a mile from the beach and within walking distance to tons of shops and restaurants! Complete with a full bathroom, mini fridge, microwave, outdoor shower, and patio area, this cozy room is perfect for a relaxing beach getaway.

4.98 out of 5 average rating, 101 reviews

Jamaica Couples Getaway

Newly renovated downtown studio unit perfect for a couple (or single traveler). Located right next to jolly rogers water park and within walking distance to several bars and restaurants. Condo is an efficiency so a smaller space than a one bedroom condo but very cute and cozy.

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Other great holiday rentals in Chincoteague Bay

5 out of 5 average rating, 19 reviews

Home in Snow Hill

The Puskar’s Landing

CandaceRating, 5 stars2 weeks ago

Such a beautiful home! It also was very cozy and peaceful. The beach and pier is a nice walk away and the hot tub was perfect for relaxing. Host was very friendly and responsive if we needed anything. I will most definitely be staying here again!

4.94 out of 5 average rating, 85 reviews

Guest suite in Berlin

The Burley Bungalow

KristinRating, 5 stars5 months ago

Wanted a quick getaway over New Year's and this was absolutely perfect! Location was easy walking distance to downtown Berlin and the accommodations were exactly as described! Five-star recommendation for sure! Thank you Ben an Kelsey!

4.88 out of 5 average rating, 76 reviews

Cottage in Westover

Martha’s Cottage•at Old Beauchamp Homestead•

EliezerRating, 5 stars5 days ago

We had a great time at Martha's place. Love the Christian theme and attention to detail. My kids enjoyed the backyard, swing and water fountain. Looking forward to going back soon. It's the perfect retreat for some quiet and peace

5 out of 5 average rating, 44 reviews

Cabin in Westover

Chalet Style Home, private country setting

AprilRating, 5 stars4 months ago

I recently stayed at Crooked Elm and was thoroughly impressed. The place was impeccably clean, and the attention to detail was evident in every corner. The host's responsiveness was top-notch! One feature that stood out was the guest binder. It was incredibly detailed, providing clear instructions on everything from using the fireplaces to local attractions and dining recommendations. This made it easy to settle in and feel at home. It had everything we needed for a cozy stay! Overall, my stay at Crooked Elm was delightful, and I highly recommend it to anyone looking for a cozy, well-managed retreat.

Campervan/RV in Salisbury

4.93 out of 5 average rating, 46 reviews

There is no place like GNOME! Camping on a farm!

JoshuaRating, 5 stars2 weeks ago

A super fun, and unique location! We had a great time exploring the local area; restaurants and shopping. And, we all slept so well! Very peaceful surroundings. The wake up call from the peacock was FANTASTIC!

4.92 out of 5 average rating, 36 reviews

Apartment in Salisbury

Studio Apt. Close to the Beach

LeeRating, 5 stars4 days ago

I would book again with Tasha, she was quick to respond with answers to questions. We felt comfortable in our surroundings. It was a very nice place to stay and very welcoming.

4.96 out of 5 average rating, 54 reviews

Guesthouse in Onancock

Holly Cove’s “Tiny” Guesthouse

TedRating, 5 stars3 days ago

An absolutely wonderful space. Cozy, as described, but it was the absolutely perfect base for my wife's and my weekend adventure in the nearby town of Onancock. The waterfront location is quiet and perfect for unwinding after a day or biking enjoying the shore. Martha could not have been more welcoming. This in addition to great communications and little touches like a goodie bag with snacks. Highly recommend a stay here for anyone visiting the area.