Holiday rentals with a pool in Westmoreland County

4.92 out of 5 average rating, 53 reviews

Flat in Colonial Beach

Sail Away To - Beachfront Views & Private Balcony

Sail Away To, CoBe Condo’s brand new, waterfront condo w/ stunning views is now available! Reach out to accommodate a group by booking our sister condo, Sail Away! → 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

4.95 out of 5 average rating, 43 reviews

New 4BR townhome in the heart of Colonial Beach

Relax and recharge at this family-friendly getaway in charming Colonial Beach, situated on the banks of the Potomac River. This townhouse is on a quiet block surrounded by water and only a short walk to the beach, restaurants & parks. There’s also a pool (heated mid April to mid Oct) and putting green only feet from the unit. This new four bedroom townhouse has multiple decks and patios -- including a rooftop with water views. It's the perfect spot to enjoy the quiet lifestyle of Colonial Beach.

4.95 out of 5 average rating, 38 reviews

Retro Retreat w/ Beaches, Pool + Tennis + Firepit

A quintessential 1970s house, characterized by bold patterns, earthy color schemes, and avocado green appliances. Geometric wallpaper and low-slung furniture dominate the living spaces. Disco-era charm extends to vibrant bedrooms; backyard boasts a lighted firepit area. This nostalgic retreat immerses guests in the groovy aesthetics of the 70s, providing a retro-cool escape. 4 beaches, a pool, and tennis. Close to Westmoreland State Pk, Colonial Beach, art galleries, great restaurants, and more.

5 out of 5 average rating, 9 reviews

Boat in Kinsale

Spend the Night on the River

Experience the charming town of Kinsale with a home base in the heart of it. This boat offers comfortable & spacious accommodations with all the perks of the marina - pool, tennis court, seasonal bar, kayaks for rent - right outside your cabin. Located on the Yeocomico River, The Slips Marina features a recently updated clubhouse where you can hang out, shower, enjoy the roof deck bar & many special events throughout the year. Note the boat does not have a bathroom, but clubhouse is nearby.

5 out of 5 average rating, 15 reviews

Water View Cozy Getaway- beach/Kayak/fishing/pool

Welcome to your ultimate waterfront community getaway! Our charming and cozy house is newly built 4 bedrooms and 4.5 bathrooms and 3 minutes Walking distance to the public beach, making it the perfect retreat for anyone looking to enjoy modern amenities in a serene and tranquil setting. Whether you're looking for a romantic getaway, a family vacation, or a peaceful retreat, our house offers a truly unique and unforgettable experience. We can't wait to welcome you to your home away from home!

4.99 out of 5 average rating, 156 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!

4.94 out of 5 average rating, 53 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.

4.97 out of 5 average rating, 89 reviews

Waterfront Gem: Dock, Hot Tub, Beach, Pool, Kayaks

Welcome to the Rivah! Lovely and inviting freshly renovated and beautifully decorated house with 5 bedrooms and 3 full bathrooms. Relax on the covered porch, large double deck with new hot tub, or our private dock. Walk the private beach and look for bald eagles, gaze at an evening fire, go crabbing/fishing, or jump in the community pool! Bring your boat + jet skis! We provide two kayaks and two standup paddle boards. There are two private community beaches in the neighborhood to enjoy!

Superhost

4.92 out of 5 average rating, 208 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.

4.96 out of 5 average rating, 46 reviews

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

★ Expansive Water Views ★ Dock ★ Outdoor community pool (May-Sept) ★ Beverage Bar & Popcorn maker ★ 3 Kayaks, Canoe, SUP & Paddle boat ★ Smokeless Fire Pit/Outdoor Lounge ★ Crab pots ★ Wood burning Fireplace ★ Level 2 EV Charger ★ 1 King Bed, 3 Queen Beds, 1 twin, 1 Queen pullout ★ Foosball ★ Games ★ Gas Grill ★ Telescope ★ Fully updated ★ Free 1G Wifi ★ Dedicated Workspace ★ 5 TVs w/Netflix & Prime 8 Miles-Montross 11 Miles-Stratford Hall 12 Miles-State Park

Superhost

Villa in Montross

4.86 out of 5 average rating, 99 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

Guest house in Colonial Beach

4.96 out of 5 average rating, 57 reviews

Beach Carriage House with Pool and Cabana

A Colonial Beach property with a heated pool, cabana, and entertaining patio with gas grill is located just steps away from a sandy bathing beach on the historic Potomac River. The Beach Carriage House includes a spiral staircase that leads up to a beautiful loft with a queen-size bed. Downstairs is a full bath with an extra-large walk-in shower as well as a comfortable living room with gas fireplace, queen-size sleep sofa, and equipped kitchenette. Holds up to 4 guests.

Holiday rentals for every style

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Cabins

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

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Westmoreland County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.8 out of 5 average rating, 25 reviews

Home in Kinsale

Riverfront Paradise w/ Hot Tub & Pool in Kinsale!

StacyRating, 5 stars3 weeks ago

From the moment we arrived, we were blown away by the breathtaking views—truly even more beautiful than the photos. The home was exactly as described: clean, spacious, and full of charm. It’s always a relief when a listing matches the real experience, and this one exceeded expectations. Even though we had some rain, there was still so much to enjoy. The house had a closet full of games for entertainment, and while we didn’t end up playing them, it was nice knowing they were there. Instead, we took full advantage of the large, well-equipped kitchen to cook a big family meal, then gathered around the even larger dining room table for laughter and connection. One of the most special parts of the trip was spending time at the dock. The hosts provided crab pots, and we were able to catch our own blue crabs and turn it into a full day of fun and delicious reward. This home gave us the space and setting to truly slow down, reconnect, and make lasting memories. Highly recommend for anyone l

4.91 out of 5 average rating, 11 reviews

New Private Beachfront panoramic view every window

HelenRating, 5 stars1 week ago

Wow!! Five stars 🌟 to Michael's place, beautiful house, I loved it. Really peaceful, beautiful view, the house is as described and in the pictures . Very helpful and friendly host. Would love to come back again

4.91 out of 5 average rating, 33 reviews

3 Little Birds

YenRating, 5 stars4 days ago

Jake was very helpful and responsive. Answered every question I had in minutes. The place was sparkling clean and in walkable distance to the beach and restaurants. My family of 6 had a very relaxed and pleasant union and stay at Jake’s place. One thing to note is that you will need to bring your own shower essentials (shampoo/conditioner and body wash). But Jake was able to provide the closest grocery store even I contacted him very late.

4.94 out of 5 average rating, 17 reviews

Stay&Play:Games, Pool, FirePit, Beach & Boardwalk!

VirginiaRating, 5 stars6 days ago

My family and I just took our first blended family vacation here! And it was everything and more than the pictures really show! This is a perfect vacation home for a family to get away! You want quite you got it! You want fun in the sun, you got it! You want endless hours of entertainment for the children, you definitely got it! Our kids didn’t think about an electronic once! My 12 year old nephew who is a Roblox lover, handed me is phone for the entire vacation! It was just truly amazing. And Tony! Is just an amazing host, from me personally God sent because our booking took faith! He had it and want to say we didn’t disappoint! As we packed up to head out our family decided that this house will be our family vacation home that we will visit! We loved the house and the accommodations and we love the host! We created a pivotal memory here! And we are forever grateful to God for Tony for allowing us to stay in his home for our first vacation ❤️

4.85 out of 5 average rating, 20 reviews

Idyllic Montross Vacation Rental Home w/ Views

Lisa JayneRating, 5 stars8 months ago

We really enjoyed the stay at the River House. We are a repeat customer and the house did not disappoint us. The host is very gracious and everything is just as the website has it listed. We enjoyed the amenities, lots of videos, games and the hottub. There is a short walk to the beach which we visited twice a day. We loved every minute of it! Thank you!

Superhost

5 out of 5 average rating, 3 reviews

Pier Pressure

AdrienneRating, 5 stars2 days ago

Highly recommend. Spacious house with lots of amenities including a pool. Well appointed kitchen with everything you need. Great location, walkable to Main Street in town.

DanaRating, 5 stars3 days ago

New place to stay

River Phoenix

A true gem! This Airbnb was absolutely beautiful! Every detail was thoughtfully curated to create a warm and welcoming atmosphere, that felt like a peaceful retreat. The space was spotless, stylish, and had great touches all throughout with something for everyone. We loved having the beautiful views and watching the wildlife. The host was very responsive and kind, making everything easy and stress-free. We would definitely stay here again and highly recommend to anyone looking for a relaxing and memorable stay on the water!