Family-friendly holiday rentals in Dover

5 out of 5 average rating, 148 reviews

Four colorful tiny cottage suites are aligned under a blue sky with fluffy clouds. Each suite features distinct pastel-colored exteriors with round windows and front doors in various hues, complemented by modern railings and landscaping that enhances the welcoming vibe.

Tiny home in Villas

Hot Tub | Mini Golf | Arcade | Gym — Coastal Quad

Welcome to The Coastal Quad, New Jersey’s first pocket resort! You will be booking a stay in one of four luxurious, 1BR tiny cottage suites, so each visit is a new adventure! You will enjoy your own private hot tub, fire pit, grill, fenced-in yard, and access to a shared rooftop mini golf course, retro arcade, full gym with sauna, office, laundry facility and more. Located just steps from a quiet bay beach and a short drive to Cape May and Wildwood, this is the most exciting resort at the shore!

4.9 out of 5 average rating, 168 reviews

The exterior of the property is illuminated at night, highlighting the path with strategically placed ground lights. The façade features a simple, white wooden structure with dark shutters, creating contrast against the soft glow of the lighting.

Guest suite in Dover

💖 Edi’s Suite *Privacy & Comfort Away From Home*

THIS IS A SMOKE-FREE PROPERTY w/ a Spacious apartment connected to my home. Large bedroom w/ queen sized bed, queen sized air mattress, living room, dinning nook, kitchenette & bathroom. Just off of the Rt. 1 exit, it's 5 miles from Dover Downs & DSU, 3 miles from Wesley College, minutes from Dover AFB, & 15 min (13.5 mi) via DE-1 S to DE Turf Sport Complex. Rehoboth Beach is 53 min (42.9 mi) via DE-1 S. Bethany Beach is 1 h 7 min (54.0 mi) via DE-1 S Dewey Beach is 53 min (43.2 mi) via DE-1 S

4.92 out of 5 average rating, 253 reviews

A cozy bedroom features a full-sized bed covered with a nautical-themed quilt. A nightstand and a dresser with multiple drawers are situated against the walls. Decorative wall art adorns the yellow walls, while soft lighting creates a welcoming ambiance. A plush area rug adds warmth to the space.

Guest suite in Lincoln

Nicencozy, near DE Turf, Bayhealth, beaches, AFB

Stay in peace at this smoke-free, quiet abode. Within 10 mins of Milford (Bayhealth Sussex, Walmart, shopping, pharmacies, restaurants, etc.). 15 mins: DE Turf, Milton, breweries. 20-30 mins: Bowers Bch, Pickering Bch, Sports at the Bch, Dover & Georgetown, theaters & casinos. 30-45 mins: other beaches and outlets. Please review Guide Book and House Manual after booking, and call us after a last minute booking, so we can tell you how to get in. Snacks, water, etc. provided while supplies last.

4.99 out of 5 average rating, 266 reviews

A welcoming space is featured, showcasing a luxurious jacuzzi with a wooden tray holding candles and decor. Nearby, a cozy living area with a modern couch is highlighted against an artistic forest mural. An adorable Highland cow stands nearby, adding a touch of rustic charm.

Ranch in Selbyville

Ranch Stay- Farm Animals, Jacuzzi, Arcade, Beaches

Welcome to the Swedish Cowboy, your ultimate escape! This unique BARNDOMINIUM home is designed to offer a memorable retreat for up to four (4) guests, with the flexibility to accommodate two (2) additional guests for a small fee. Enjoy the charming backyard where you can meet a variety of fuzzy and feathered friends or head inside and play on the arcade or relax in the jacuzzi. Perfectly situated near popular beaches and bustling boardwalks, you'll have plenty of options for fun and relaxation.

A serene view of a sandy beach leading towards the ocean is depicted. A wooden fence with wire stretches along the path, bordered by patches of tall grass. The gently rolling waves and soft sky create a calming atmosphere.

4.99 out of 5 average rating, 453 reviews

High Tech Hideaway: The modern beach lifestyle

Live the beach lifestyle with every modern convenience! Roomy 2 bedroom, 2 bath condo only 10 mins from Rehoboth, Lewes and Dewey. Surrounded by craft beer, tax-free outlet shopping, and fantastic food. Cleanings exceed CDC guidelines. Three 65" 4k TVs with 221+ channels, Apps, touchscreen Amazon Echos, dimmable LED lighting, and ultra high speed wi-fi. Fully renovated with luxurious flooring, quartz countertops, and new furniture. Free washer/dryer, free coffee, free parking, and water views.

4.97 out of 5 average rating, 635 reviews

The exterior of a two-story wooden structure is presented, featuring a staircase leading to a covered balcony. The building is surrounded by trees displaying fall foliage, creating a serene outdoor atmosphere. A gravel area is noted at the base, with a vibrant red and white camper positioned nearby.

Flat in Greenwood

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

4.84 out of 5 average rating, 258 reviews

A shared outdoor space showcases a large pool with a tiled hot tub, surrounded by lounge seating. In the background, a playset and a whimsical playhouse are visible amid lush greenery, creating an inviting area for relaxation and family fun.

Flat in Lincoln

Waterfront Studio • Pool • Near DE Turf & Beach

Discover a stunning studio nestled along the Cedar Creek, steps from Route 1. Perfectly situated, it’s only a 10-min. drive to the DE Turf Complex, & charming shops and restaurants of Milford. A quick 15-min. trip to the beach. This cozy retreat accommodates four guests, with room to stretch upto 6! Enjoy waterfront views right from your unit. Unwind in our year-round hot tub or take a dip in the seasonal pool and spa during the summer months. Warmly welcome families, pets & contractors!

4.95 out of 5 average rating, 146 reviews

A modern kitchenette features wooden cabinetry with a spacious sink and various kitchen appliances, including a toaster oven and coffee maker. Open shelving displays decorative containers and essential utensils, while a wall clock adds a touch of functionality. A towel hangs neatly from a hook.

Flat in Magnolia

Perfect Rental for Dover Attractions & BayBeaches

15 minutes from Dover Nearby casinos, beaches, and the racetrack. Bowers and Slaughter beaches are about 10-15 mins from us, whereas, the major beaches like Rehoboth, Lewes and Dewey are 45mins to an hour from us. We are 5 mins from Highway 1 and located 15 mins from DE Sports Complex 10 mins from Highway 13 (Dupont Ave) Near the mall, casino, racetrack, shopping, and many restaurants. Killens Pond State Park is a 10 min drive. Harrington Casino the Del. State Fair is 15 mins from us.

4.95 out of 5 average rating, 186 reviews

A cozy sleeping area features a spacious bed with a quilted grey coverlet. Two decorative yellow pillows are positioned at the head of the bed. A small bedside table holds a lamp and books, while a colorful area rug adds warmth to the space.

Tiny home in Lewes

Cozy Woodland Cottage

Enjoy the sounds of nature when you stay in this unique place. Located less than 5 miles from downtown Lewes and Delaware Beaches. The cottage guest house is nestled in the woods adjacent to a tree house overlooking a tranquil pond with a calming fountain sounds. On the main property guests have access to a in ground swimming pool (seasonal) with a 60 foot lap lane and slide, schedule times with hosts.. The backyard also includes an organic garden, playground and 🐔 chickens.

4.96 out of 5 average rating, 114 reviews

A single-story home is set amidst a lush, green lawn, surrounded by trees and natural vegetation. The exterior features a light-colored facade with a welcoming front entry and flower beds to the sides, enhancing the serene atmosphere of the wooded location.

Home in Greensboro

Cozy 2 bedroom home on wooded private lane

Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.

A spacious living area features a comfortable sectional sofa with decorative pillows, complemented by a large area rug. A television is positioned on a stylish media console, while large glass doors provide access to a private patio, framed by blue curtains. A ceiling fan is present above.

4.97 out of 5 average rating, 115 reviews

1st Floor Beach-town Condo in Lewes

Come stay at our favorite little beachtown condo in Lewes! This 1st floor 2 bedroom, 2 bath condo has everything you need for an enjoyable and relaxing vacation! You will be just a few miles to the beach and outlet malls, have access to the community pools (May-Sept), park, and sport courts, and will be within walking distance to several great restaurants and shops. While we are "pet friendly" only 1 pet (dog or cat, 40lb maximum) is allowed per the HOA rules.

Superhost

A comfortable living area features a cozy gray sofa facing a stone fireplace. A wooden coffee table sits on a decorative rug, while a flat-screen TV is mounted on the wall. Light enters through a nearby window, illuminating the space.

Guest house in Dover

4.83 out of 5 average rating, 161 reviews

Country Guest House

Relax with the whole family at this peaceful place to stay on the farm. You will see horses, cows, goats, chickens & ducks. Family friendly. Animals roam the property & are safe to pet. You will hear many farm noises such as roosters crowing, cows mooing & more. This home is located in the country & a min of 5 miles from stores and shopping. Full kitchen, 1 full bathroom & 1 queen bed included. Upon request Queen Air Mattress or Twin Bed can be provided.

Popular amenities for Dover family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Casa particular in Chestertown

A spacious lawn is surrounded by tall trees, leading to a two-story house with a porch. Soft evening light casts a gentle glow, while a hammock can be seen suspended between two trees, inviting relaxation in the outdoor space.

4.93 out of 5 average rating, 168 reviews

Red, White & Waterview Studio Apt with pool

4.97 out of 5 average rating, 153 reviews

A cozy living area features two brown leather sofas, a patterned rug, and a soft ottoman. A reading nook is created with a gray chair draped in a yellow blanket. Natural light streams in through a large window, with plants and bookshelves enhancing the space.

Home in Chestertown

Cozy 3-bedroom home w/ Hot tub & firepit

4.99 out of 5 average rating, 313 reviews

The exterior of a quaint house features a black and white design with a front porch adorned by a vibrant American flag. The gravel pathway leads to the entrance, surrounded by small potted plants and a spacious, tree-lined yard.

Bungalow in Town Bank

Romantic Saltbox Bungalow! HOT TUB! Bay Sunsets!

Superhost

The master suite features wooden beams and log walls, creating a rustic atmosphere. A plush bed is positioned next to a classic bench. Soft lighting illuminates the space, while a colorful woven rug adds warmth to the wooden floor.

Cabin in Goldsboro

4.85 out of 5 average rating, 161 reviews

Wigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views

4.99 out of 5 average rating, 150 reviews

A spacious living room features a large sectional sofa and a floor-to-ceiling gas fireplace. Natural light filters through the plantation shutters, highlighting decorative plants and a round mirror. A large TV is mounted above a white-brick fireplace, creating a cozy gathering space.

Home in Villas

Hot Tub Holiday Escape! Fireplace + backyrd oasis!

4.96 out of 5 average rating, 142 reviews

Home in Rehoboth Beach

Rehoboth Beach Gem – Hot Tub + EV Charger 2 BR

4.95 out of 5 average rating, 225 reviews

Cottage in Charlestown

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

4.96 out of 5 average rating, 119 reviews

An outdoor space features a heated swimming pool surrounded by a concrete patio. Comfortable seating options include several couches and chairs. A large umbrella provides shade, while a hot tub is positioned nearby. String lights and greenery enhance the backyard ambiance.

Home in Lower Township

Relaxing Getaway

Family- and pet-friendly home rentals

4.91 out of 5 average rating, 228 reviews

A serene gravel lane is framed by tall trees, creating a natural canopy. Sunlight filters through the leaves, creating a dappled effect on the path below. The surrounding greenery contributes to a peaceful and quiet atmosphere, ideal for relaxation.

Guest suite in Greenwood

Woodsong Suite & Getaway!

4.95 out of 5 average rating, 151 reviews

The interior of the bus features a cozy layout with wood paneling and large windows providing natural light. A comfortable seating area, equipped with pillows, is situated next to a compact kitchen with a stove and cabinets. A small dining table with two placemats is visible.

Bus in Frankford

Delightful Skoolie Near Bethany Beach

4.95 out of 5 average rating, 152 reviews

The exterior of the cabin displays a rustic design with wooden accents and large windows that invite natural light. A spacious grassy area surrounds the structure, complemented by trees and landscaping. A small patio area is visible, offering a place to sit outdoors.

Farm stay in Chestertown

Outrange at Blue Heron Farm

Guest house in Rehoboth Beach

The structure features a modern design with a wooden exterior and large glass windows. A spacious deck is accessible from the upper level, surrounded by lush greenery. The ground floor includes a stone facade with garage doors, creating a harmonious blend with the natural surroundings.

4.86 out of 5 average rating, 338 reviews

The Winkler

Guest suite in Chestertown

A serene waterfront view reveals calm water framed by lush green trees. A small private dock is visible, featuring an orange kayak resting at the edge. The scene conveys tranquility, inviting relaxation amidst nature.

4.99 out of 5 average rating, 241 reviews

Beautiful Waterfront Chestertown Getaway

Superhost

A spacious dining area features a large wooden table surrounded by eight chairs. A decorative mirror hangs above the table, reflecting warm light from a unique pendant fixture. A doorway leads to a well-lit bedroom, with the bed visible through the open door.

Home in Rehoboth Beach

4.88 out of 5 average rating, 144 reviews

Secluded Coastal Cottage • Just 9 Min to the Beach

4.95 out of 5 average rating, 207 reviews

A wooden picnic table is positioned on a grassy area, surrounded by trees. A fire pit made of metal is placed nearby. The lush greenery provides a natural backdrop, with dappled light filtering through the leaves.

Campsite in Ocean View

Tent Camp Site 2, Good Earth near Bethany Beach

Place to stay in Rehoboth Beach

A comfortable living area features a green sofa and two coral armchairs, accompanied by a round wooden coffee table with decorative items. A stylish indoor/outdoor fireplace is centrally positioned beneath a wall-mounted television, with a vibrant area rug adding warmth to the space.

4.99 out of 5 average rating, 259 reviews

Stylish, Spacious & Dog-Friendly Studio Cottage

Family-friendly home rentals with a pool

A serene bedroom features a spacious bed adorned with a textured navy quilt, flanked by two bedside tables with lamps. Natural light enters through a window, illuminating the light blue walls. A dresser and decorative mirror complement the calming atmosphere.

4.99 out of 5 average rating, 158 reviews

Family Friendly Top Floor Condo Near Boardwalk

A balcony view captures a wide expanse of lush green fields and dense trees, framed by a soft gray sky. The natural landscape offers a serene backdrop, highlighting a peaceful atmosphere. A railing can be seen in the foreground, providing a sense of depth.

5 out of 5 average rating, 147 reviews

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

4.79 out of 5 average rating, 283 reviews

A spacious outdoor pool is surrounded by brightly colored buildings, featuring vibrant blue umbrellas and stacked lounge chairs. The pool reflects the sky, inviting relaxation, while the white railings create a barrier between the pool area and the well-maintained walkways.

Apartment in Wildwood

Cozy Wildwood Crest Beach - Poolside Condo

A dining area is showcased with a grey table set for six, surrounded by vibrant yellow chairs and a metal wire-frame chair. A modern light fixture hangs above, and a decorative wreath adorns the wall, complemented by abstract artwork on either side.

4.98 out of 5 average rating, 197 reviews

Renovated Condo Near Outlets, 3.5 Miles to Beach

An inviting living area features a dark grey couch complemented by a decorative blue pillow. A wooden dining table accommodates six chairs, positioned near a softly lit ceiling fixture. A television rests on an earthy-toned cabinet, while an open kitchen area is visible in the background.

4.85 out of 5 average rating, 135 reviews

2b 2b condo! 2 master bedrooms! rehoboth beach

A bright living area features a light-colored sofa and armchair with coastal patterns. A wooden coffee table sits on a textured rug, while a mounted television is visible on the wall opposite. The open layout allows for glimpses of a dining area with a table set for six.

4.98 out of 5 average rating, 108 reviews

First Floor Comfort and Convenience

A comfortable living area features a dark sofa adorned with patterned throw pillows. A coffee table sits atop a patterned area rug, while natural light enters through multiple windows adorned with wooden blinds. A TV is positioned on an entertainment unit across from the seating area.

4.95 out of 5 average rating, 138 reviews

Beautiful condo in Villages of Five Points, Lewes