Holiday rentals with a pool in Westmoreland County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Westmoreland County

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Guest favourite
Home in Montross
4.98 out of 5 average rating, 131 reviews

3+N PROMO-Waterfront w/Gamerm, Firepit, Dog+EV OK

*Ask about our 3+ Night promotion* ☀️ Waterfront 🛶 Kayak/Paddleboard 👨‍🍳 Gas griddle ⛱️ 3 Community Beaches 🔥 Fire pit 🐶 Dogs OK (Max 2) 🎯 Gameroom ⚡️EV Outlet Relax - Star Gaze - Kayaks/Paddleboard - Hike - Fish - Swim - Beach & more! If you're looking to take a break or connect with nature, the Riverside Retreat in Montross, VA offers a peaceful sanctuary that is perfect for families, small groups, & couples Book your getaway today or ❤️ us for next time!

Top guest favourite
A bright living area features a spacious light-colored sectional sofa, paired with a small coffee table. Two framed bird prints adorn the walls, and natural light fills the room through large windows. A floor plant adds a touch of greenery beside a modern armchair.
Home in Colonial Beach
4.98 out of 5 average rating, 44 reviews

Beautiful townhome in charming Colonial Beach

Welcome to Colonial Beach Escape! Located in the heart of Colonial Beach on the POTOMAC RIVER, our brand new family-friendly townhome offers tasteful, comfortable furnishings and all the amenities you need for a fun getaway. Colonial Beach Escape boasts 4 bedrooms, 3.5 baths, 3 private outdoor spaces, and is steps from the community pool (opens April 18!) and putting green. We are just 3 blocks from the beach and a short walk/golf cart ride to many restaurants, breweries, shops, and playground.

Guest favourite
A comfortable living area features a navy blue sofa adorned with patterned cushions, complemented by a wooden coffee table. Large windows provide a view of the water, while natural light fills the space. A ceiling fan and indoor plants add to the ambiance.
Flat in Colonial Beach
4.88 out of 5 average rating, 64 reviews

Sail Away - Beachfront & Stunning Balcony Views

Sail Away, CoBe Condo’s brand new, waterfront condo w/ stunning views is now available! Reach out to accommodate more by booking our sister condo, Sail Away To! → Private patio w/ 180° views, perfect for a morning coffee or wine at sunset → Access to pool (owners and guests only) → 1,025 ft² of stylish, cozy space, steps from the water and restaurants → Master suite which looks upon the water → Fully equipped kitchen and living room, smart TVs → Reserved parking space → ❤️ of Colonial Beach

Top guest favourite
A spacious rooftop deck is presented, featuring comfortable seating arranged around a fire pit. A patterned area rug adds texture to the wooden surface. Clear views of the sky and surrounding greenery create an inviting atmosphere for relaxation.
Apartment in Colonial Beach
4.97 out of 5 average rating, 63 reviews

Rooftop bay and river views

Watch sunrise & sunsets overlooking the Potomac River and Monroe Bay on the rooftop deck. Your new, modern, spacious townhome(end unit), fully furnished with everything you need AND DOG FRIENDLY. This quiet family friendly town has walkable restaurants or rent a golf cart and explore. Separate levels with tv's so kids and adults can be on separate floors. Relax by the rooftop fire pit or in the HEATED pool. 2 adjacent parks kids love! Close to the city, but world's apart! $100/dog/stay

Guest favourite
An aerial view captures the single-story home situated on a private peninsula, surrounded by water. Lush green lawns and trees frame the property, while a dock extends into the bay. A pool is visible in the backyard, adding to the outdoor amenities.
Home in Abell
5 out of 5 average rating, 10 reviews

New, Waterfront Home w/ Island on St. Clements Bay

Wake up to breathtaking panoramic views of St. Clements Bay at this newly renovated 4-bedroom waterfront retreat in Abell, MD. Perched on a private peninsula, the home features a 160-ft dock for crabbing and fishing, bay beaches, an island, pool, hot tub and endless space to relax by the water. Paddle to your own private island to sit on the beach, swim, or explore. With kayaks, crab pots, beach chairs, and a Weber grill included, its everything you need for the perfect waterfront escape.

Top guest favourite
A wooden dock extends toward a tranquil waterway, framed by tall grass and a colorful sunset. The sky features hues of orange and purple, reflecting on the water's surface. The scene invites relaxation and appreciation of nature's beauty.
Home in Montross
4.98 out of 5 average rating, 173 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!

Guest favourite
A serene sunset view over the Potomac River is captured, with gentle reflections shimmering on the water's surface. Silhouette of tall grasses frame the image in the foreground, while silhouettes of docks are visible along the shoreline.
Home in Montross
4.94 out of 5 average rating, 65 reviews

Brigadoon, the BRAND NEW Waterfront Haven

Relax with your whole family at our peaceful home. Discover an oasis of serenity at this stunning 3-bedroom, 2.5-bath retreat boasting panoramic views of the Potomac River from every window. Marvel at breathtaking sunrises and sunsets, from your own private beach, immersing yourself in the tranquility of the landscape. Situated just 2-3 hours from the Washington, DC Metro Area, 2 hours from Charlottesville, and 1 hour from Richmond, this haven offers an easy escape into nature's embrace.

Guest favourite
Guest house in Hague
5 out of 5 average rating, 10 reviews

Bell House

Two-bedroom guesthouse with deck overlooking the Lower Machodic Creek (Coles Point, Hague VA) the perfect setting for enjoying sunrise and sunset. Shared property, but the second floor guesthouse is all yours. The first floor is a garage we use for storage. Salt water lap pool, 100 feet of beach on Lower Machodic Creek with expansive views of the Potomac River, kayaks, private dock, and 20 acres to explore. Great for a family vacation, couples getaway, girls weekend, you name it!

Guest favourite
A private beach area is depicted with soft, sandy ground, featuring two beach chairs under a blue umbrella. Calm waters extend to the horizon, complemented by a wooden dock and a distant view of the opposite shore under a clear, blue sky.
Home in Montross
4.92 out of 5 average rating, 224 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.

Guest favourite
A serene view of a private beach meets the calm waters of the bay under a clear blue sky. Gentle waves lap at the sandy shore, with a wooden dock extending into the water. Soft grasses frame the beach area, contributing to the tranquil atmosphere.
Villa in Montross
4.85 out of 5 average rating, 113 reviews

Beach Retreat

Relax with the whole family at the Beach Retreat! Enjoy the beautiful Sunrise and Sunsets in the Hot tub overlooking your own private beach! There is plenty to do in the Northern Neck of Virginia! We have Wineries, a Brewery, historical sites, boating, swimming, fires on the beach, bike rides, kayaking, plenty of Summer and Fall Festivals and so many great places to eat on and off the river! The Northern Neck of VA is a hidden gem! Just a 90 minute drive from the DC area

Top guest favourite
An open living space features a modern kitchen with stainless steel appliances and white cabinetry. A wooden dining table with light-colored chairs is positioned centrally, accompanied by a cozy seating area. Large windows provide natural light and a view of the adjoining four-season porch.
Cottage in Montross
4.98 out of 5 average rating, 52 reviews

Harbor Cottage

Nestled in a beautiful water community you'll find this modernized cottage. Harbor Cottage is a bright and open A-frame single family home, perfect for a quiet and cozy retreat. Relax on the four-season porch with panoramic views! Get outdoors and enjoy hiking, biking, bird watching or fossil hunting. A short 5 minute walk you'll find a riverbank beach perfect for sunbathing, shell collecting, kayaking, fishing and stunning sunrises.

Top guest favourite
A spacious bedroom features a light-colored bed with a floral-patterned coverlet. A small nightstand and a lamp provide soft lighting. Large glass doors open to a serene outdoor view, with a light green wall and plush carpet completing the inviting space.
Guest house in Leonardtown
5 out of 5 average rating, 49 reviews

Breton Bay Guesthouse ~ ~ No cleaning fee

Located in the preferred Breton Bay Golf & Country Club neighborhood, this immaculate guesthouse is a 900 square foot detached dwelling with fully equipped kitchen, living room, separate large bedroom, bathroom with shower, washer and dryer, and balcony. Will consider setting up the space to accommodate your child and/or infant/toddler. Plenty of parking -- enough room for your personal watercraft or small boat!

Popular amenities for Westmoreland County rentals with a pool