Vacation rentals in Issue

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Top-rated vacation rentals in Issue

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Guest favorite

Cottage in Newburg

4.88 out of 5 average rating, 66 reviews

Cozy Farm Cottage Near Fishing/Boating in the DMV

Welcome to Wilson Family Farm! Located an hour south of Washington, D.C., Wilson Cottage is surrounded by trees, cropland and river marshes. The Cottage is perfect for a romantic getaway, a vacation with the kids and the family dog or a relaxing solo retreat. Sparkling clean 43” tv with Amazon Fire /Dish TV Wifi (rural internet service can be spotty) No crowds or traffic Public tennis court, fishing pier and playground 1/4 away. Two miles from kayaking area Five miles from Cobb Island Marina

Sep 26 – Oct 3

G$31,308 GYD per night

Guest favorite

Home in Newburg

4.92 out of 5 average rating, 103 reviews

The River House, a Wicomico Beach Retreat

Located right on the water of the Wicomico River with a private sandy beach, The River House will become your favorite retreat! This 4.5 bdrm, 3 bath fully stocked home has all the convenience of modern construction (including wifi) but maintains the vintage charm of the original property. The one acre lot is very private with spectacular forest & water views. Fun can be found in every direction and for all ages! It has two bottom floor bed/bath combos & a fabulous sleeping loft for the kids!

Nov 30 – Dec 7

G$43,045 GYD per night

Guest favorite

Cottage in Colonial Beach

4.91 out of 5 average rating, 116 reviews

Shore Cottage Getaway - Water access

Enjoy relaxing at your cozy "Shore Cottage." Two bedroom one full bath cottage sleeps 4-6 people. Owners bedroom has queen size bed and Tv. Second bedroom has a Full size mattress bunk bed. Fully equipped kitchen and back deck grillin'! Enjoy relaxing on your front porch across from Monroe Bay. Walk to your private beach on the Potomac River. Also enjoy free access to your local marina on Doctor Point, where you can kayak, boat and even fish. Minutes from the winery, restaurants and parks!

Sep 25 – Oct 2

G$34,137 GYD per night

Guest favorite

Cottage in California

4.97 out of 5 average rating, 193 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has been completely remodeled. The open floor plan allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum and St. Leonard Volunteer Fire Department featuring live concerts by top name bands.

Oct 4 – 11

G$18,502 GYD per night

Guest favorite

Cottage in Colonial Beach

4.98 out of 5 average rating, 124 reviews

River view dog friendly YOLO Beach House

YOLO Beach House has a gorgeous sunrise view only one block to the river & blocks to the beach. Fenced yard excellent for children & dogs (dog door to back yard). Recently updated. Walking distance to Dockside, Castlewood park & the boat landing. Beach is pet friendly Oct to Mar only. The house & property are no smoking. Home has a whole home backup generator that does a self-check on Monday morning. It will start automatically if power is lost. We hope you enjoy YOLO as much as we do!

Aug 7 – 14

G$30,368 GYD per night

Guest favorite

Apartment in Leonardtown

4.98 out of 5 average rating, 119 reviews

Stunning Sunsets on Breton Bay, Seaside apartment

Charming efficiency apartment decorated with a coastal theme overlooks Breton Bay. Use of pier for hanging out... or crabbing and fishing. Apartment is in the second floor of detached garage on the premises of a private home. Beautiful serene surroundings 5 min. from downtown Leonardtown with shopping, restaurants and events. Area offers historical sites, wonderful parks, a large Mennonite and Amish community, great restaurants and friendly people! 25 minutes from Solomons Island.

Jun 20 – 27

G$28,917 GYD per night

Guest favorite

Cabin in Colonial Beach

4.97 out of 5 average rating, 102 reviews

Spring Perfect, Water Front A-frame on Winery

This serene cabin is on the Ingleside Vineyard's property. Have a glass or two of wine and walk around the vineyards and then retreat to your own private a-frame cabin oasis. A beautiful view of the Roxsbury Estate where abundant wildlife can be viewed all around the property and the pond is stocked and ready to be fished. Within driving distance to wineries, Stratford Hall, George Washington & James Monroe's birthplace, Westmoreland State Park, and the beach town of Colonial Beach.

Nov 9 – 16

G$27,877 GYD per night

Guest favorite

Guesthouse in Bushwood

4.92 out of 5 average rating, 143 reviews

Little House by the water

Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. However, the space is small and it is really a studio apartment as I think the pictures make evident.

Jan 31 – Feb 7

G$18,509 GYD per night

Guest favorite

Apartment in Lexington Park

5.0 out of 5 average rating, 315 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!

Sep 24 – Oct 1

G$18,327 GYD per night

Guest favorite

Tiny home in Solomons

4.95 out of 5 average rating, 538 reviews

“Cabana by the Bay”-tiny home on a pier!

This tiny home is a newly renovated cabana sitting on a pier. Fall asleep to the sound of waves crashing under you! Enjoy shared use of our private beach. Kayaks and bikes are available April-October and are stored directly across the street. Go crabbing or fishing off the pier and walk to one of the many nearby restaurants. Check out the summer concert series at the Calvert Marine Museum.

Oct 23 – 30

G$29,758 GYD per night

Guest favorite

Guest suite in Colonial Beach

4.9 out of 5 average rating, 62 reviews

Private entrance 2 bedroom suite in new home

Walk to a secluded beach or enjoy a fire in the fire pit on the grass outside your suite. Private unit with outside entrance in new home. Two queen bedded rooms plus a sofa that converts to a queen bed in the living room. Continental breakfast, coffee, and ice await you. Quiet area close to all the fun Colonial Beach has to offer.

Jun 25 – Jul 2

G$19,126 GYD per night

Guest favorite

Home in Colonial Beach

4.99 out of 5 average rating, 198 reviews

Beach Blonde Cottage

Coastal farmhouse style cottage recently renovated and on "The Point" in Colonial Beach. Located 3 blocks from the water on a quiet street. Downtown attractions are close enough to walk, bike or access by golf cart. Dahlgren per diem welcome.

Mar 3 – 10

G$32,935 GYD per night