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Holiday rentals in Delmarva Peninsula

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Top-rated holiday rentals in Delmarva Peninsula

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Tiny home in Cambridge

4.89 out of 5 average rating, 496 reviews

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette 5 min away from Blackwater Refuge! It is an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! Staying the cabin will make your visit even more memorable!The Tiny Cabin is now located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

23–30 Sep

$117 SGD per night

Guest favourite

Farm stay in Madison

4.98 out of 5 average rating, 163 reviews

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

11–18 Jul

$171 SGD per night

Guest favourite

Tiny home in Accomac

4.93 out of 5 average rating, 440 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!

11–18 Apr

$171 SGD per night

Guest favourite

Farm stay in Onancock

4.99 out of 5 average rating, 174 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!

8–15 Oct

$247 SGD per night

Guest favourite

Flat in Greenwood

4.97 out of 5 average rating, 479 reviews

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)

24 Nov – 1 Dec

$114 SGD per night

Guest favourite

Loft in Lusby

5.0 out of 5 average rating, 312 reviews

Coastal Treetop Retreat w/ Private Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons, and Calvert Cliffs. Private garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen (convection oven, induction stove, microwave, refrigerator, and Keurig). Enjoy quick Wi-Fi, a 40" Smart TV, a cozy queen bed, and comfy lounge chairs. Bring S'mores fixings to roast over the fire and wrap yourself in a blanket. Choose to stay in or adventure out.

19–26 Jan

$177 SGD per night

Guest favourite

Flat in Frederica

4.97 out of 5 average rating, 258 reviews

Smokefree Lakeside Relaxation

Quiet smoke free lakefront Carriage House studio over garage with separate entrance. Mini Fridge, microwave, dishes. Use of fire pits, canoe, SUP, dock. Lake is fishable and swimmable. Flatscreen HDTV with Premium Channels. WiFi to use with your own device or use my laptop in unit. 45 min from beach. 20 minutes to Dover. 4 parks with walking paths within 10 miles. Close to Dover Air Force Base but not in flight path. Well behaved social pets with responsible owners are welcome!

27 Oct – 3 Nov

$100 SGD per night

Guest favourite

Home in Cape Charles

4.99 out of 5 average rating, 104 reviews

Modern Private Beach House close to Cape Charles

A sanctuary, an oasis, a one of a kind experience communing with nature while lounging in civilized splendor—all are apt descriptions of this New York architect designed beach house on the shores of the Chesapeake Bay. Guests enjoy stunning waterfront views from a finished floor height of 36 feet. The Eastern Shore of Virginia is famous for its flat tidewaters, but this property is perched amongst unusual relic Sandhills, complete with pines, gum trees and vast sea and sunset vistas.

11–18 Sep

$1,466 SGD per night

Guest favourite

Guest house in Easton

4.99 out of 5 average rating, 545 reviews

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for two individuals (No children under 8 years of age.), and please limit your visit to one vehicle only.

22–27 Mar

$199 SGD per night

Guest favourite

Flat in Lexington Park

5.0 out of 5 average rating, 316 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

21–28 Nov

$122 SGD per night

Guest favourite

Cottage in Onancock

4.97 out of 5 average rating, 195 reviews

Escape to the Eastern Shore - Upscale Waterfront

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

1–8 Sep

$250 SGD per night

Guest favourite

Guest suite in Chincoteague

4.93 out of 5 average rating, 224 reviews

Baywatch North-Waterfront & Roaming Ponies

This is a lovely space! 2 queen bedroom 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, patio cooking area shared with upstairs unit, bbq grill, fantastic view, beach items, plenty of parking, private lane, very quiet out of the way of everything, super laid back host living in the other portion of the house. Labrador and cat on premises, ponies on premises!

21–28 Oct

$143 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Houses

A space that's all yours, with room for everyone

Popular amenities for Delmarva Peninsula holiday rentals

Free parking on premises

Air conditioning

Other great holiday rentals in Delmarva Peninsula

Guest favourite

Tiny home in Snow Hill

4.89 out of 5 average rating, 226 reviews

Private cottage and gardens/comfortable queen bed.

10–17 Aug

$172 SGD per night

Guest favourite

Cottage in Deal Island

4.93 out of 5 average rating, 119 reviews

Water View Cottage

1–8 Nov

$209 SGD per night

Guest favourite

Guest suite in Berlin

4.99 out of 5 average rating, 149 reviews

Berlin/Ocean City Suite- Relax/Refresh near beach!

11–18 Oct

$158 SGD per night

Guest favourite

Cottage in Heathsville

4.94 out of 5 average rating, 179 reviews

HedgeRow, Deer Haven in the NNK- Dock & Boat Ramp

4–11 Mar

$170 SGD per night

Guest favourite

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 293 reviews

Historic St.Mary's City at the Lazy Bear Cottage

1–8 Aug

$114 SGD per night

Guest favourite

Cabin in Deltaville

4.97 out of 5 average rating, 253 reviews

"The Little Red Cabin" aka The Galley

27 Mar – 3 Apr

$153 SGD per night

Guest favourite

Flat in Milton

4.96 out of 5 average rating, 132 reviews

Beachin' Inn Milton

13–20 Sep

$165 SGD per night

Guest favourite

Cottage in Westover

4.99 out of 5 average rating, 181 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

3–10 Feb

$467 SGD per night

Destinations to explore