Holiday rentals in Westmoreland County

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!

4.98 out of 5 average rating, 135 reviews

Guest suite in Warsaw

The Osprey Nest: Rappahannock Riverfront Suite

Sunny, private 2nd floor suite at the river's edge features panoramic views of the Rappahannock and surrounding farmland. Take in fiery sunsets, sunrises, starry skies, eagles, ospreys and more. Swim, fish, explore waterways by kayak, or bike in tranquil, rural surroundings. Morning coffee on the balcony with the songbirds is a treat, and the riverfront deck, surrounded by trees is sublime. Restaurants, historic sites, hiking, fossil hunting, wineries, antiques & more are a short car ride away.

Holiday home in Colonial Beach

4.97 out of 5 average rating, 122 reviews

The Observatory on Rose Manor

The Observatory on Rose Manor is a private home. It’s 2 blocks from the heart of downtown & beach. Colonial Beach is the golf cart capital of Virginia, we all drive them here. Rent one when your in town. Just over an hour south of DC. This small town takes you back in time with events & local charm. This brand new rental is on the grounds of Rose Manor. Rose Manor was built 1896 it operated as the New Willard hotel for over 50 years. Come relax on its huge porches & enjoy the water view.

4.96 out of 5 average rating, 191 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.

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

Flat 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.

4.96 out of 5 average rating, 156 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.

5 out of 5 average rating, 105 reviews

Waterfront Cottage in Colonial Beach at Placid Bay

Luxury Cottage with private water views full of natural wildlife. You will love the open floor plan with a chef's kitchen stocked with All the essentials including beverages and coffee. Sleep late with private bedrooms that include luxurious bedding Enjoy the expansive outdoor space complete with Patio, Pergola, Fire Pit, and large deck with outdoor kitchen. Walk down to the 28ft foot dock where you can fish, relax in the sun or take the Kayaks for a ride Close to DC and NOVA

4.93 out of 5 average rating, 160 reviews

Guest house 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.

4.96 out of 5 average rating, 250 reviews

Home in Montross

Stunning Lake House Retreat on the Potomac River

This beautiful lakeside home offers the perfect sanctuary for your next retreat, nestled along the Potomac River just two hours from the D.C. metro area. It is spacious enough for any large family gatherings or groups of friends. Lounge with a gorgeous view or start a ping pong/pool game. Whether embarking on your next fishing adventure, kayaking, biking, playing yard games or simply relaxing in our luxurious jacuzzi, your visit will surely be one to remember.

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.

4.98 out of 5 average rating, 107 reviews

Home in Montross

Waterfront Retreat| Kayak+Beaches+Pool | Gameroom

Relax ✧ Kayak ✧ Paddleboard ✧ Hike ✧ Fish ✧ Swim ✧ Beach & more at the Riverside Retreat in Montross! ☀️ Welcome to our modern waterfront sanctuary with kayaks + paddleboard 🏊‍♀️ 3 community beaches + pool (open Memorial to Labor Day) 👨‍🍳 Gas griddle for cooking a delicious meal 🔥 Fire pit + Gameroom (ping pong, arcade, & more!) 🐶 Dogs Welcome ⚡️EV Charging Book today or ❤️ us for next time

Holiday rentals for every style

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Quaint homes, peaceful surroundings

Popular amenities for Westmoreland County holiday rentals

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Pool

Free parking on premises

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Other great holiday rentals in Westmoreland County

5 out of 5 average rating, 20 reviews

Home in Avenue

200 Year-Old Waterfront Home only 1.5 hours fromDC

ReneeRating, 5 stars2 weeks ago

It was peaceful and serene. I wanted a place to relax and let the issues of the world fade away. That's exactly what I experienced at Skip-A-Way Landing. The house is not only beautiful but it has a warm and welcoming feel to it. Like coming home after a long time away. Overall the house is lovely however the subtle touches throughout are also much appreciated. It's the small details that let you know that the owners put a lot of thought into it and care about its' guests. I did not want to leave. I'm already looking forward to going back. Highly recommended!

4.95 out of 5 average rating, 97 reviews

Cottage in Cobb Island

Happy Hour~Riverfront, countyside, private pier

LisaRating, 5 stars1 month ago

As always, just an awesome getaway! The minute I pull up to the cottage and look out at the water, any stress just disappears. I’ve been coming here for a number of years and Angela and her cottage are second to none!! Angela is a wonderful host and provides great directions and recommendations and the cottage is just perfect. Thank you Angela for having this little gem!!!

4.98 out of 5 average rating, 45 reviews

Home in Montross

Game Themed Water Fun! Boats+Pool+Beach+King Bed

AlishaRating, 5 stars6 days ago

Absolutely beautiful stay! The cabin has the cutest theme and the proximity to the water was great and a gorgeous view. Abby and family was so kind, responsive, and great hosts. Would highly recommend this getaway!

4.96 out of 5 average rating, 70 reviews

Home in Newburg

Beautiful, serene waterfront property

JonathanRating, 5 stars1 month ago

An incredible peace of property! This house has been beautifully renovated and exceeded every expectation. Unbelievable waterfront views from nearly every room in the house, back porch and fire pit. Also a very nice surprise of having a little play area stocked with toys for the little ones! This is a must stay if we’re ever back in the area!

Superhost

4.75 out of 5 average rating, 48 reviews

Family Tides: Hidden Gem, Colonial Beach Getaway

KellyRating, 5 stars1 week ago

We loved our stay! The house was cleaner than any hotel we’ve used. There was plenty of room for our family of 6, and I got the best sleep in ages thanks to the super comfortable bed and soft linens. We were impressed by how thoughtfully the house was stocked with anything we could need: great selection of games in the dining room, laundry supplies including stain remover, kid-friendly dishes, etc. We appreciated the clear instructions posted by appliances. The neighborhood was peaceful and safe, and we felt comfortable letting our teens walk down to the beach each evening to watch the gorgeous sunset. We enjoyed the nearby towns, with great experiences at El Toro, Colonial Buzz Espresso Bar, Muse Pizzeria, Westmoreland State Park, and the Westmoreland County Museum. The location even made for easy day trips to Washington DC and the Pax River Naval Air Museum. Thanks again, Dani, for making our first ever family vacation such a great experience!!

4.98 out of 5 average rating, 65 reviews

Serene, well-appointed waterfront retreat

ErinRating, 5 stars3 weeks ago

This house and the amenities are amazing. It was perfect for our family reunion with 5 couples. Enough room for everyone to have space. My favorite part was gathering around the round dinner table with the 10 of us. We also took the kayaks out and up Mattox creek for a wonderful morning of a peaceful paddle. The Lodge was perfect for my husband and I to step away from the group and have some privacy. I highly recommend!!

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!