Holiday rentals with a pool in Rockingham County

4.93 out of 5 average rating, 265 reviews

A spacious living room features a large sectional couch and an accent chair, both positioned on a patterned area rug. A wall-mounted TV is visible, with light streaming through the windows, highlighting the natural wood flooring and airy design.

Home in Derry

Sanctum by the Lake

Looking for a place to bring the family, or a get-a-away with friends? This is it! From the light and airy design that makes it feel like home to the large pool, hot tub, and lake access, The Sanctum by the Lake has everything you need for a great stay. It is a short 100 yard walk from the lake and a quick drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston or the NH Seacoast, close to the Lakes Region, White mountains, and great skiing spots as well as the famous NH Outlets.

5 out of 5 average rating, 99 reviews

A heated pool is set within a stone patio, surrounded by lush greenery. Two lounge chairs are positioned nearby, while modern heating units stand along the patio's edge. The pool's clear water reflects the surrounding area, offering a serene outdoor retreat.

Home in Ogunquit

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach

Welcome to your Ogunquit Oasis, a luxurious 5-bedroom beach house located on the edge of Ogunquit Village. Walk to the beach, restaurants, Perkins Cove, Marginal Way & everything in Ogunquit! The house features a heated pool that reaches 104 degrees, ideal for all seasons. Built in 2014, the house includes central air, three Ultra HD TVs, and wireless speakers. The dining table seats 10, with an outdoor living room, grill, & gas firepit. Each spacious bedroom offers plush bedding & ceiling fans.

4.93 out of 5 average rating, 136 reviews

A spacious living area features a comfortable sectional sofa with patterned upholstery, situated alongside large windows offering expansive views of the waterfront. Natural light floods the room, complemented by warm wooden accents on the ceiling and floor. A dining table for four is placed near the windows.

Cottage in Newburyport

Sunset Waterfront Retreat | Private Beach, Pool &

Waterfront retreat with private beach access, panoramic marsh views, and unforgettable sunsets. Designed for families and groups looking to relax, reconnect, and enjoy the best of Plum Island living. Enjoy the private pool (open seasonally), expansive outdoor living spaces, firepit lounge, and peaceful wildlife views directly from the property. Spend your days walking the island, to local beaches and restaurants, or simply unwinding by the water. Inside, the home features a modern kitchen, was

4.9 out of 5 average rating, 52 reviews

Surfside - Boutique Studio Condo w/Pool

SURF-THEMED CONDO IN THE HEART OF HAMPTON BEACH! Just 208 ft from the beach and steps from all the excitement. Enjoy a fun coastal vibe with surf-inspired décor, a covered heated pool, and a fully furnished, well-equipped condo featuring a toaster oven, full fridge, cooktop & microwave. Walk to restaurants, shops, arcades, and nightlife. Includes Wi-Fi, Smart TV, and 1 covered parking spot. 🌊🏄‍♂️☀️ No need for a morning coffee run as we provide coffee, tea, sugar & cream during your stay.

4.97 out of 5 average rating, 62 reviews

A spacious bedroom is presented, featuring a dark wooden bed frame with a light-colored bedding set. Two nightstands with lamps are positioned on either side. Natural light enters through three windows, complementing the warm tones of the wooden floor and subtle wall color.

Home in Kittery

Fantastic Kittery Home with Pool

Modern New Englander boasting a large, private backyard with pool (seasonal, from May to Oct, approx). Our comfortable, 3-bedroom home is a commuter's dream. Working from home? Use our separate dedicated office space with 1 gig WiFi. Playing hooky? So many options! Walk or bike to the fabulous eateries, shopping or breweries our area has to offer! Enjoy our pool or take a short drive to the beach! (Please note, our pool is normally unheated. For an additional $40 a day we'll heat it!)

The sleeping area features a queen Murphy bed with a soft white quilt and decorative pillows. Beside the bed, two lamps provide warm lighting, and a framed wall art piece in neutral tones is displayed above. Ample storage is available in stylish cabinetry.

4.94 out of 5 average rating, 54 reviews

Whale's Tale - Boutique Studio Condo w/Pool

FRESHLY UPDATED & IN THE HEART OF HAMPTON BEACH! 208ft across from the main beach & located only steps from all the excitement. Covered & heated pool. Furnished & fully-equipped condo w/ Keurig coffee machine, toaster, fridge & microwave. Easterly facing unit, so you can hear the roar of the Atlantic Ocean & enjoy the ocean breeze! No need for a morning coffee run as we provide coffee, tea, sugar & cream during your stay. Wifi, cable, chromecast & smart TV. Parking for 1 car included.

5 out of 5 average rating, 10 reviews

Flat in Pittsfield

Eaton Pond Retreat

Nestled on Catamount Mountain, this peaceful mountain retreat offers the perfect blend of relaxation and outdoor adventure. Enjoy scenic views from the gazebo, unwind by the firepit, take a dip in the pool, or launch a kayak right from the property’s pond. Surrounded by hiking trails, nearby lakes, and classic New Hampshire beauty, it’s the perfect escape year-round. Plenty of parking for trailers (boats and Snowmobile). Plenty of parking. message me if you have any questions.

4.79 out of 5 average rating, 48 reviews

A classic red-shingled house is depicted, featuring multiple gabled roofs and a welcoming front porch. A paved pathway leads to the entrance, bordered by landscaped greenery. The parking area is visible alongside the building, with a mix of outdoor lighting and natural shade from nearby trees.

Flat in Haverhill

Cozy 2BR Haverhill Stay | Pool & Parking

🏡 Escape to this peaceful 2BR Haverhill retreat, perfect for couples, families, business travelers, and extended stays. Relax with a King bed, a Queen bed, a private fire pit, and a shared fenced backyard, with optional seasonal pool access (June–September, $50/hour). Inside, enjoy fast WiFi, a Smart TV, a fully equipped kitchen, dining for six, free parking, and easy access to downtown Haverhill, commuter rail, scenic trails, shopping, and convenient Boston day trips.

An aerial view of Hampton Beach highlights the proximity of the condo to the beach and nearby attractions. The coastline stretches out with sandy shores and a vibrant blue ocean. Nearby buildings and roadways are visible, providing a sense of the community and access to the area.

4.84 out of 5 average rating, 103 reviews

Steps from Beach | Pool | Parking | Large Deck

This furnished 2-bedroom, 2-bath condo is available for monthly stays from mid March through April, offering a comfortable coastal home base just steps from Hampton Beach. The unit features high-speed WiFi, central heat and A/C, one off-street parking space, and access to a covered common pool (open seasonally during summer months). Ideal for professionals, couples, or extended winter stays seeking walkable beach access without sacrificing comfort, privacy, or flexibility.

Superhost

An open living area is visible, featuring a gray sofa, a patterned yellow armchair, and a dining table with six chairs. Large sliding glass doors provide access to a balcony, offering views of the outdoors. A kitchen counter and a coffee machine are also present.

4.82 out of 5 average rating, 34 reviews

Serenity by the Sea

Welcome to Serenity by the Sea! This postcard is the perfect place to get away and enjoy the smell & views of the ocean from your own balcony. This cozy place has it all for you to bring your family, or to get away from the hustle and bustle of daily life. You will enjoy beautiful North Beach, which offers a place to relax by the ocean or take a walk to find the perfect shell and seaglass. I hope you enjoy the space as much as I do! Welcome home.