Holiday houses in Coles Point

4.97 out of 5 average rating, 162 reviews

Home in Hague

Osprey's roost: Spring and summer 2025

Hidden treasure! Come join the osprey along the Potomac River in the Northern Neck of Virginia! This 4 bedroom/3 bath custom home is at the end of a quiet lane and sits on a point of land between the Potomac River and Blackbeard’s Pond, making for magnificent river views from sunrise to sunset. Enjoy swimming, canoeing, Bocce on the lawn, barbecue on the deck! Osprey’s Roost is the perfect retreat to rest and recharge, ideal for a romantic week away, a girls’ weekend or a family gathering!

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 348 reviews

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

Inquire first on pets, there is a 50 lb. weight limit total, can be split up between 2 small dogs or 1 at 50lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

4.96 out of 5 average rating, 190 reviews

Cottage in Leonardtown

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

4.99 out of 5 average rating, 155 reviews

Beach Please! River cottage w/private beach & dock

Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

5 out of 5 average rating, 108 reviews

Home in Piney Point

Living on Island Time

Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

5 out of 5 average rating, 117 reviews

Home in Leonardtown

White Point Cottage -- Quiet Waterfront Getaway

Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

4.98 out of 5 average rating, 135 reviews

Apartment in Leonardtown

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.

4.95 out of 5 average rating, 155 reviews

Cabin in Colonial Beach

Summer 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.

Superhost

4.92 out of 5 average rating, 207 reviews

The Glebe

This 3br 2ba home with own private beach is nestled off of the Potomac River and boasts serene and expansive views. Sunbathe on the private beach, cool off in the water, go fishing/crabbing from the dock, or just listen to the waves crash. Whatever it is, you’ll find it absolutely relaxing. Be sure to explore local wineries, breweries, shops and enjoy the community pool and tennis court. It's the perfect getaway house for couples/families or anyone looking for a serene weekend.

4.93 out of 5 average rating, 159 reviews

Guesthouse in Bushwood

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.

Apartment in Lexington Park

5 out of 5 average rating, 383 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!

4.99 out of 5 average rating, 156 reviews

Cottage in Hague

Potomac River cheerful cottage

Embark on a journey to the serenity of nature and the gentle lullaby of the Potomac River at the cottage. Escape the hustle and let the timeless embrace of water and tranquility rejuvenate your mind and soul. The private sandy beach (no public access) is steps away and awaits your footprints. Delight in the serene surroundings of the Northern Neck countryside. Two hours from DC, Richmond and Maryland.

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Other great holiday rentals in Coles Point

4.94 out of 5 average rating, 16 reviews

Home in Kinsale

Nature's Retreat

JessicaRating, 5 stars1 month ago

Was looking for a nice and relaxing getaway and this place delivered! It was clean and I was impressed that the kitchen had everything stocked. Check-in was easy and the hosts were communicative.

Cottage in Leonardtown

4.92 out of 5 average rating, 225 reviews

Potomac River Freedom Cottage

SarahRating, 5 stars3 weeks ago

We were in town for a swim meet, and Greg’s place was perfect for our crew! We all slept soundly in the comfortable beds. We cooked every meal in the fully stocked kitchen. The view, the walk to the adorable little beach, and the peaceful surroundings were a bonus we had not experienced before during past trips! Greg is extremely responsive and helpful. We would absolutely book again!

4.9 out of 5 average rating, 166 reviews

Tranquil River Home

ElizabethRating, 5 stars2 months ago

Our 3-day stay at Emy's was perfect for us - two adults and a dog. The home is spacious, well-furnished, supplied with common everyday items and the view is awesome (the home is situated on a high cliff). Lots of spaces to sit/eat/enjoy the outdoors and even the gale-force winds were exciting to experience. At this time of year, the neighborhood was not busy and we were able to walk streets and leisurely stroll to the lake, the beach and the boat ramp. One of our favorite things - the proximity of the Westmoreland State Park and the Geo Washington Monument National Park. Lots of beautiful trails that we loved walking. The home was very comfortable for all of us; our 70-pound dog was able to fully use the outdoor space because it was securely fenced and the grounds were clean and clear of obstacles. Thank you, Emy. We appreciated the opportunity to visit your home and hope to do so again.

5 out of 5 average rating, 22 reviews

Cozy cottage with water access

ToddRating, 5 stars2 weeks ago

Great for a group/family weekend getaway. Erin and Aryn are very hospitable hosts and provided all the essentials. Everything in the kitchen and all the light switches are clearly labeled, making it easy to navigate.

4.95 out of 5 average rating, 19 reviews

Home in Coltons Point

The Eventide at Serenity Lane

JulieRating, 5 stars2 weeks ago

What a great find! We loved our stay and enjoyed the special touches that made us feel right at home. Definitely recommend and will be back!

Superhost

Home in Leonardtown

4.91 out of 5 average rating, 32 reviews

Abells Wharf Cottage - Natural Splendor Getaway

BrianRating, 5 stars8 months ago

We enjoyed our stay at Jan's cottage. Very clean, spacious and very good amenities. Jan was very responsive and informative on local places to visit/eat. The property is beautiful and peaceful. Just what we needed to have a relaxing weekend. Will visit again, Highly recommend!