Holiday rentals in Chincoteague

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Top-rated holiday rentals in Chincoteague

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Guest favourite

Cottage in Chincoteague

4.92 out of 5 average rating, 129 reviews

Maggie’s Cottage on Poplar - Our Happy Place!

Step back in time and enjoy the simplicity of this 2 bedroom, 1 bath vintage Chincoteague cottage located in the heart of town. Quaint, quiet and cozy - Maggie’s Cottage is the perfect retreat to slow down, relax, and enjoy an island get away... anytime of the year! Maggie’s Cottage is just right for a couples get away, girls trip, a solo retreat, or a small family vacation. Well stocked and comfortable- you will feel right at home. Walking distance to local dining, shopping and waterfront!🐴🦪🌅

24–31 Jan

€ 202 per night

Guest favourite

Cottage in Chincoteague

4.94 out of 5 average rating, 112 reviews

Pony Pines!Your Waterfront Getaway Cottage Awaits!

Imagine a quiet retreat on the water where the sunsets are magnificent, and wildlife such as geese, raccoons, deer, owls, and egrits are to be experience in the backyard. Pony Pines offers a firepit, a master bedroom with a jacuzzi tub, and a clawfoot tub on the main floor. We have 2 Kayaks for your use on the canal, and a storage shed with some of the beach accessories you may need for your days at the Ocean. Linens are provided! Relax with your whole family at this peaceful, Happy Place.

2–9 Oct

€ 332 per night

Guest favourite

Tiny home in Accomac

4.93 out of 5 average rating, 439 reviews

Little Red House on a Farm - Quiet Rural Waterview

The Little Red House VA is a tiny house with big charm. This rural cottage on a 50 acre farm is nestled between peaceful fields, woods, marsh and creek. Curated with hygge comfort and efficiency in mind, you'll love the natural light and serene decor. • Epic stargazing • Heavenly private outdoor shower • Firepit with wood provided • Ample open spaces • Peace and quiet for sleeping • Comfy patio seating for chilling, coffee, and cocktails • Fast Starlink WIFI. • Proud Superhost for 10+ years!

16–23 Sep

€ 138 per night

Guest favourite

Farm stay in Onancock

4.99 out of 5 average rating, 172 reviews

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!

29 Aug – 5 Sep

€ 185 per night

Guest favourite

Tiny home in Snow Hill

4.89 out of 5 average rating, 225 reviews

Private cottage and gardens/comfortable queen bed.

Private cottage and gardens, comfortable Queen bed, full bath and kitchenette, within walking distance to historic Snow Hill. 30 min. drive to Ocean city and Assateague Island National park. This cottage was once a old school woodworking shop which is now on display at the old iron furnace town museum nearby. This beautiful three hundred year old town sits on the beautiful Pocomoke river with canoe, kayak, and bike rentals. Museums, art galleries, speciality shops, food and entertainment.

5–12 May

€ 132 per night

Guest favourite

Home in Accomac

4.98 out of 5 average rating, 217 reviews

Heartsong Farmhouse , a nature lover's retreat.

Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

15–22 Oct

€ 176 per night

Guest favourite

Home in Chincoteague

4.96 out of 5 average rating, 126 reviews

Charming Island Home "Sandy Pines"

Come and enjoy a nice, relaxing vacation at this charming island home. "Sandy Pines" lies just a half a block from the water and a block and a half from the bridge to Assateague (where the beach is. The downstairs features a living room and dining room, 2 bedrooms (equipped with two twin beds each), a lovely kitchen, full bathroom and screened porch. On the second level you'll find the master bedroom with a private full bathroom, movie/game/yoga room, and a 2nd fully screened porch.

9–16 Sep

€ 316 per night

Guest favourite

Home in Chincoteague

4.98 out of 5 average rating, 191 reviews

★ Pearl in the Pines: Kayaks-Fire Pit-Bikes-Beach-Pet Friendly

Fully equipped 1200 sf home-3 Bdrm residence-with fire pit, 2 kayaks, 4 bikes, towels & linens. Pearl in the Pines is literally at nature's front door within a few miles from Assateague National Seashore (the beach), home of the world famous Chincoteague Ponies. Enjoy: Swimming in the bay and ocean Bicycling Fishing, crabbing, clamming Kayaking, paddle boarding; boating Hiking Bird Watching Nature photography Hunting Nature Trails Great Restaurants & Brew Pub Boat Tours Ponies

25 Nov – 2 Dec

€ 196 per night

Guest favourite

Guest suite in Chincoteague

4.98 out of 5 average rating, 231 reviews

Baywatch Upper-Waterfront & Roaming Ponies!

Absolutely beautiful space in and out! Situated right on the bay with views of Assateague across the way, Chincoteague ponies are on premises and sometimes come right down in front of the house. Coastal charm at its finest, there are 2 queen bedrooms and one twin bed in a center, extra hang-out breakfast room, all with a view. No full kitchen. Microwave, toaster, small fridge, stocked Keurig coffee and tea station and shared outdoor cooking area included in this upstairs unit.

3–10 Nov

€ 202 per night

Guest favourite

Cottage in Onancock

4.97 out of 5 average rating, 194 reviews

Waterfront romantic getaway Eastern Shore w dock

A waterfront getaway at the newly renovated Westview Cottage on Onancock Creek just off the Chesapeake Bay. Wake up to beautiful water views through floor-to-ceiling glass doors. A private, peaceful escape in the country conveniently surrounded by fields and wildlife complete with a dock for crabbing and fishing (seasonal) 4 MI to Downtown Onancock & Restaurants 4.5 MI to Walmart 25 Mi to Camp Silver Beach 35 MI to Chincoteague Island 39 MI to Cape Charles

7–14 Dec

€ 195 per night

Guest favourite

Flat in Chincoteague

4.83 out of 5 average rating, 110 reviews

Island Sunset Downtown Haven

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 and Wifi - Linens provided

14–21 Aug

€ 249 per night

Guest favourite

Tiny home in Machipongo

4.98 out of 5 average rating, 252 reviews

Machipongo Glamper

Close your eyes. Imagine a salty breeze and a view of a vineyard from your spot tucked into the back of our rural 5 acre spot. The stars are brighter, the clams are saltier, and the pace is slower. At night, the stars go on forever and in morning a perfect view of the sun rising over the neighbor’s field.

6–13 Jan

€ 79 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Chincoteague holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Chincoteague's top sights

Island Creamery35 locals recommend

Ropewalk Restaurant - Chincoteague24 locals recommend

Bill's PRIME Seafood & Steaks30 locals recommend

Don's Seafood Restaurant27 locals recommend

Pico Taqueria34 locals recommend

Veterans Memorial Park4 locals recommend

Other great holiday rentals in Chincoteague

Guest favourite

Cottage in Chincoteague

4.98 out of 5 average rating, 128 reviews

Waterfront-CI Bay sunsets-Amazing views

30 Jan – 6 Feb

€ 337 per night

Guest favourite

Tiny home in Cambridge

4.99 out of 5 average rating, 154 reviews

Blackwater Refuge House on The Farm, water access

2–9 Aug

€ 111 per night

Guest favourite

Guest house in Chincoteague

4.94 out of 5 average rating, 54 reviews

Cozy Beach Cottage

8–15 Jan

€ 113 per night

Guest favourite

Home in Chincoteague

4.96 out of 5 average rating, 73 reviews

Breeze on Inn

18–25 Dec

€ 114 per night

Superhost

Home in Chincoteague

4.87 out of 5 average rating, 75 reviews

"3 Sisters" Ivy's Cottage-Lovely downtown cottage

4–11 Oct

€ 166 per night

Guest favourite

Home in Chincoteague

4.95 out of 5 average rating, 94 reviews

Adorable Beach Cottage Just Steps From Town & Bay

22–29 Dec

€ 203 per night

Guest favourite

Loft in Pocomoke City

4.98 out of 5 average rating, 56 reviews

Cozy Barn Loft: Country Views & Central to Beaches

18–25 Sep

€ 162 per night

Guest favourite

Treehouse in Machipongo

4.95 out of 5 average rating, 20 reviews

Treehouse Couple's Retreat

25 Feb – 4 Mar

€ 184 per night

Show all

Quick stats about holiday rentals in Chincoteague

Total rentals	600 properties
Rentals with a pool	150 properties have a pool
Pet-friendly rentals	160 properties allow pets
Family-friendly rentals	540 properties are a good fit for families
Total number of reviews	12K reviews
Nightly prices starting at	€ 38 before taxes and fees

Holiday rentals in Chincoteague

Top-rated holiday rentals in Chincoteague

Cottage in Chincoteague

Cottage in Chincoteague

Tiny home in Accomac

Farm stay in Onancock

Tiny home in Snow Hill

Home in Accomac

Home in Chincoteague

Home in Chincoteague

Guest suite in Chincoteague

Cottage in Onancock

Flat in Chincoteague

Tiny home in Machipongo

Holiday rentals for every style

Houses

Cabins

Cottages

Popular amenities for Chincoteague holiday rentals

Stay near Chincoteague's top sights

Other great holiday rentals in Chincoteague

Cottage in Chincoteague

Tiny home in Cambridge

Guest house in Chincoteague

Home in Chincoteague

Home in Chincoteague

Home in Chincoteague

Loft in Pocomoke City

Treehouse in Machipongo

Quick stats about holiday rentals in Chincoteague

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore