Holiday rentals with a pool in Reading

Guesthouse in Chester Springs

A bedroom features a spacious bed with a light grey blanket, flanked by two nightstands with lamps providing soft lighting. A dresser with drawers and a woven basket are positioned nearby. A large mirror reflects the tranquil space, enhancing its openness.

4.96 out of 5 average rating, 281 reviews

Newly Renovated Chester Springs Guesthouse

The newly renovated one bedroom apartment (that can accommodate up to 5 guests) above the detached garage at Artisan Studios provides a lovely guesthouse retreat. Nestled in the woods in beautiful Chester County, you'll enjoy privacy and seclusion even though you're just a 5 minute drive to anything you could need. We're just 8 miles from the PA Turnpike and only 38 miles (45 minutes to an hour) from Philadelphia. Feel free to bring your pet, as long as they are house broken or litter trained.

4.89 out of 5 average rating, 559 reviews

An inviting outdoor area is illuminated by soft string lights, creating a cozy ambiance. Comfortable seating is arranged around a small table, surrounded by well-maintained greenery. The cabin's rustic wooden exterior is visible in the background, set against a twilight sky.

Tiny home in Alburtis

Glamping Cabin~Gazebo/ HotTub~1.5 NYC/ 1~Philly

Welcome/todos son bienvenidos~Hot tub/365 days/yr~Pool is seasonal. A romantic getaway. Comforts/amenities of a cabin with an atmosphere of camping. Experiential get-away/private gated/fenced property. Gazebo~panels, furniture,gas firepit & hot tub. Detached bathroom behind cabin.Outdoor shower, Hammock, BBQ’s, Wood firepit. Reconnect w/the outdoors.Queen bed w/firm mattress.Escape the cities to privacy. Abutted on 3 sides by a farm/pasture views.Easy to get to from points east in NYC & Philly

4.97 out of 5 average rating, 119 reviews

Home in Auburn

11-Acre Farmhouse Retreat | Creek, Pool, Hot Tub

✨ Peaceful Creekside Farmstead Getaway! Located on 11 acres of serene land, this farmhouse offers a perfect mix of relaxation and adventure and is an entire farmhouse offering private, peaceful accommodations! ★ Private Outdoor Pool ★ Game Room with Pool Table & Ping-Pong ★ 52" Smart TV for entertainment ★ Free Wi-Fi ★ Fire Pit & Blackstone Griddle ★ 7-Person, 93-Jet Hot Tub for relaxation ★ Creekside Views with a bridge in front of the house ★ Spacious Outdoor Area perfect for kids to play!

4.98 out of 5 average rating, 155 reviews

The outdoor patio area features a spacious pool surrounded by lounge chairs. An outdoor seating arrangement with a fire pit is positioned before the pool, inviting relaxation. The stone farmhouse and trees in the background complete the serene retreat atmosphere.

Villa in Morgantown

Mill Road Farmhouse: Restored with Beautiful Pool.

The Mill Road Farmhouse is a destination in and of itself. Immaculately restored inside and out, this home is a true retreat in the middle of Amish Country. We have a feeling you will be spending all of your time relaxing by pool and hot tub during the warmer months (or maybe grilling up a feast in the brand new outdoor kitchen area) and curled up next to one of the four indoor fireplaces during the winter months. And then of course end each day star-gazing while sitting around the campfire.

4.91 out of 5 average rating, 126 reviews

A spacious two-story home is situated on a well-kept lawn, framed by lush greenery. The property features a paved driveway leading to a large garage, while gentle hills create a serene background under a partly cloudy sky.

Guest suite in Oxford

Spacious country oasis with pool and pet allowed

More guests upon request. Large solar heated pool and roomy, pet allowed space on over one acre. Your own private space; property is shared-host occupies seperate area on 1st floor. You have a large private living area that opens to a porch including; Family room, streaming service w/42" tv with surround & large sectional couch. Kitchenette area with a sink, fridge, mini-oven, hotplates, and dishes/silverware. If you would like, Amish style sticky bread, juice & fruit served for breakfast.

4.97 out of 5 average rating, 134 reviews

A two-story house is surrounded by lush greenery and colorful plants. The exterior features a mix of brick and siding, complemented by purple shutters. A set of stairs leads to the front door, while a shaded porch provides a welcoming entryway.

Home in Coatesville

King’s place, hot tub Pool is closed until Spring

New hot tub, above ground pool with deck built into it ! Recently remodeled, Centrally located on a 1 acre lot. Not far from all the tourist attractions that Lancaster has to offer. 1 hr from philly airport, 15 minutes from downingtown, 15 minutes from gap,and 20 minutes from Intercourse. A quiet neighborhood with a spacious back yard, which is great for kids. Whether you bring cornhole, use the grill, or sit around the propane fire pit. The yard and large back deck have so much to offer!

4.96 out of 5 average rating, 599 reviews

A dining area is presented with a farmhouse-style table surrounded by metal chairs. A wooden centerpiece filled with glass vases holds fresh flowers. A stone fireplace is adorned with greenery and decorative items, while a vintage sign adds character to the space.

Bungalow in Lancaster

The River Nook in Lancaster

Our cozy three bedroom, two bathroom riverside cottage comfortably sleeps 6-8 adults, includes a 3 sided fireplace, fully stocked kitchen, and multiple seating areas both indoors and outdoors. Scandinavian, rustic/modern decor includes a hanging rope bed. Outdoor pavilion and spacious backyard in a quiet neighborhood make this the perfect getaway! *5 min to downtown Lancaster *5 min to the Riverdale Manor *10 min to Dutch Wonderland *15 min to Sight & Sound Theater *40 min to Hershey Park

4.86 out of 5 average rating, 119 reviews

An open and airy living space showcases a dining area with a wooden table surrounded by white chairs. Natural light pours through large windows, illuminating the polished wood floors. A sectional couch is positioned in the corner, while the kitchen and other areas are visible in the background.

Home in Coatesville

Peaceful Retreat Pool and great outdoor space

Peaceful and spacious home on a 2 acre lot with a small above ground pool. Great outdoor space with fire pit and seating area. Located just minutes from beautiful Lancaster County. 15 to 30 minutes from most local attractions. Philadelphia is about an hour away. There is an Amish farm market nearby. Our place is great for families with children, couples, business travelers and more. *Please read the entire listing before you decide to book and message me with any questions you may have.

4.94 out of 5 average rating, 297 reviews

A modern living area is characterized by exposed wooden beams and a cozy fireplace. Two spacious sofas are positioned around a central coffee table, with natural light streaming in through large windows. Artwork adorns the walls, adding a touch of personality to the space.

Home in Honey Brook

Ode to the '70's - hot tub & pool in Honey Brook

4 bedroom/2 bath home - modern renovation with retro flair. Large backyard with saltwater pool, hot tub, grill, fire pit, and kids playhouse! (Pool open May-Sept) We've furnished this home with our favorite pieces to create a space that inspires creativity & life. Pickleball courts within walking distance in local park. Paddles and balls provided. Close to the Honey Brook Thrift Store, September Farms & other local attractions! 1/2 hour to Lancaster City, Exton/King of Prussia.

4.94 out of 5 average rating, 336 reviews

Guesthouse in Lititz

The Grey Wolf (studio-style loft suite)

Enjoy the clean, comfy, eco-friendly & private loft space with your own private HOT TUB! Situated on top of a hill in the beautiful lake area of Lititz, PA, you will enjoy lovely views and quiet privacy. The main house is detached & adjacent to the loft suite. The loft is located on the top floor of the carriage house. Explore charming downtown Lititz just 4 miles away! Pool open Memorial Day-Labor Day. Hot tub open year round. ONE parking space/EV charging fee

4.99 out of 5 average rating, 247 reviews

The front entrance of the home features a well-maintained pathway bordered by lush greenery and flowering plants. An elegant lamp post stands beside the path, illuminating the approach to the entrance where double doors and a decorative American flag are positioned.

Apartment in Chadds Ford

Silo Suite

Welcome to our charming suite located in the heart of the historic Brandywine Valley. Nestled within the entrance of a beautifully converted 12,000 square foot barn home, this space offers a truly unique and memorable stay. Our special place is perfectly situated between the renowned Brandywine River Museum and the Chadds Ford Winery, and in just minutes, you can explore the enchanting beauty of Longwood Gardens or dive into the world of history at Winterthur.

4.96 out of 5 average rating, 151 reviews

A patio area features a set of white outdoor furniture, including a table and several chairs, arranged on a stone surface. A large tree provides shade, while expansive green fields and rolling hills can be seen in the background under a partly cloudy sky.

Apartment in New Tripoli

Countryside Suite

Take a break and unwind at this peaceful oasis. This beautiful, cozy countryside suite is located in an area where there is a lot to do. If you like the outdoors, shopping, wineries distilleries, breweries or just plain relaxing in the country, this is the place for you. We are a short driving distance to all local restaurants, hiking/biking trails, kayaking, and shops. Access to the pool and a private patio are included in the price of the rental.

House rentals with a pool

4.98 out of 5 average rating, 116 reviews

Home in Manheim

92 Acre Beautiful Farmhouse with in-ground pool

4.87 out of 5 average rating, 99 reviews

The exterior of a spacious two-story home is shown, featuring a combination of white and stone walls. Lush green grass surrounds the property, with trees and shrubs providing additional greenery. The home is set against a serene sky with scattered clouds.

Home in Douglassville

Smoker Family Estate, 5 BDR Home w In- Ground Pool

4.95 out of 5 average rating, 152 reviews

A country-style kitchen features mint green cabinetry and a wooden countertop. Stainless steel appliances include a microwave, oven, and dishwasher. A deep farmhouse sink is positioned beneath a window adorned with light curtains, while a bowl of fruit and kitchen essentials are displayed on the counter.

Home in Strasburg

Findley Farm View Cottage (Outdoor Pool!)

4.97 out of 5 average rating, 118 reviews

Home in Peach Bottom

Cozy home- heated pool & waterfall heated all year

4.94 out of 5 average rating, 127 reviews

A panoramic view showcases a clear swimming pool surrounded by a spacious deck. Lounge chairs and umbrellas are positioned along the poolside, with lush greenery and trees in the background. The inviting outdoor space provides a serene atmosphere for relaxation.

Home in Downingtown

Lakefront Guesthouse

4.98 out of 5 average rating, 121 reviews

The exterior of a single-story brick home is featured, showcasing a neatly paved driveway and a well-maintained front yard. Colorful flower beds surround the entrance, complemented by large potted plants on the porch. The inviting facade exudes a sense of warmth and welcoming.

Home in Kinzers

Country Land Guest House

4.95 out of 5 average rating, 180 reviews

The exterior of a welcoming A-frame home is shown, featuring a spacious porch with wooden railings. Two seating areas, including a swing and chairs, are surrounded by greenery and colorful flowers. A flag and hanging plants add a bright touch to the inviting entrance.

Home in Jonestown

Relax in your lower-level living space and enjoy.

4.91 out of 5 average rating, 163 reviews

A dining area is presented with a large wooden table surrounded by six light-colored chairs. Soft light fixtures hang overhead, and large windows are adorned with flowing drapes. A sideboard with decorative items complements the space, which is finished with warm wooden flooring.

Home in Glen Mills

Sweet home w/pool & woods at peaceful Glen Mills

Condo rentals with a pool

The hotel building features a modern design with multiple stories and a red roof. Surrounding greenery provides a serene environment, while balconies offer outdoor access. The property is set against a backdrop of gently rolling hills under a clear blue sky.

Hershey 2BR Suite Villa nearby Park w/indoor pool

A three-story resort building is framed by manicured lawns and trees, showcasing a red-tiled roof and green balconies. Surrounding hills create a serene backdrop, while the driveway leads to the entrance. The structure features multiple windows, allowing natural light to brighten the interiors.

4.91 out of 5 average rating, 32 reviews

2BR Unit @ Resort | Heated Pool, Gym, BBQ, Games

The exterior of the resort is showcased, featuring a multi-story building with a red roof. Surrounding green lawns and trees create a natural setting, while distant rolling hills can be seen in the background, providing a sense of openness.

Smell the Chocolate from Hershey Park 2BD Condo

A well-lit outdoor pool area is framed by a charming gazebo featuring a set of black chairs and a table. The swimming pool displays a gentle curvature, complemented by lounge chairs positioned nearby. A multi-story building is visible in the background, contributing to the resort atmosphere.

5 out of 5 average rating, 11 reviews

The Suites at Hershey- 2 bdrm sleeps 8

A scenic view of a theme park is showcased, featuring a wooden roller coaster and vibrant amusement rides against a backdrop of lush greenery and distant hills. Colorful flowers in the foreground provide a touch of natural beauty to the landscape.

Hershey, PA- Hershey Resort-2Bd Suite - BG

4.91 out of 5 average rating, 33 reviews

An inviting inground pool is surrounded by a spacious stone patio and lush greenery. Several lounge chairs, shaded by umbrellas, are positioned along the edge. Guests are enjoying the water while others are gathered nearby, creating a lively and relaxed atmosphere.

Condo in Ephrata

The Highland Oasis

The entrance to Suites At Hershey is framed by well-maintained landscaping, featuring neatly shaped bushes and vibrant flowers. The sign above reads 'Clubhouse & Registration,' indicating the welcoming atmosphere of the property. Bright blue skies and fluffy clouds enhance the inviting appearance.

5 out of 5 average rating, 7 reviews

2 Bedrooms, 2 Bath Suites at Hershey Resort Lux

The exterior of the resort is presented, featuring a multi-story building with a red roof and multiple balconies. The surrounding green landscape and gentle hills create a serene backdrop, while a clear sky enhances the vibrant setting.

5 out of 5 average rating, 4 reviews

Hershey 2BR Resort Villa nearby Hershey Park

Other holiday rentals with a pool

5 out of 5 average rating, 98 reviews

A cozy sleeping area features a spacious bed with a light-colored coverlet and a decorative pillow that reads 'RELAX.' Two comfortable chairs are positioned nearby, and large glass doors allow natural light to fill the room, offering views of the outdoor space.

Guest suite in Lancaster

Relax off of Pine

4.91 out of 5 average rating, 85 reviews

Home in Myerstown

Hershey Retreat | Pool, Spa, Sauna, Plunge, & Pond

4.76 out of 5 average rating, 41 reviews

A serene backyard features a spacious patio with comfortable seating arranged around a fire pit. A hot tub is situated nearby, surrounded by greenery. The two-story home stands in the background, showcasing a well-maintained exterior with large windows and a wooden fence.

Home in Paradise

Family home with Pool, Hot-tub & Pickleball court!

5 out of 5 average rating, 55 reviews

An open-concept kitchen and dining area features a large wooden dining table with seating for ten. Exposed wooden beams line the ceiling, complementing the stone accent wall. An island with seating for three is positioned near modern kitchen appliances, creating a welcoming space for gatherings.

Home in Quarryville

Modern Farmhouse: Pool, Hot Tub & Pickleball

5 out of 5 average rating, 99 reviews

A luxury swimming pool is surrounded by serene landscaping, including a large tree. Comfortable seating is arranged nearby, with a spacious covered porch visible in the background. The house features a combination of modern architecture and natural elements, enhancing the outdoor living space.

Home in Lancaster

Idyllic estate, close to downtown and the Amish.

4.89 out of 5 average rating, 9 reviews

Home in Washington Boro

Lancaster Retreat-Hot tub, River & Farm Views

5 out of 5 average rating, 60 reviews

A cozy living area features a small dark wooden table adjacent to a wall-mounted TV. Antique decor accents the warm golden walls, while a decorative fireplace is flanked by soft lighting. A woven basket holds books and candles atop a dark trunk, adding character.

Guest suite in Telford

Poet’s Corner | Private 4 Room Guest Suite