Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A bright bedroom features a twin bed adorned with a colorful striped blanket and a decorative pillow. Natural light enters through a window dressed with sheer curtains, illuminating the space. A blue dresser sits nearby, complemented by soft lighting from a lamp.
Apartment in Middletown
4.89 out of 5 average rating, 216 reviews

Newport Beach Retreat

Adorable 2 bedroom 2nd floor apartment located exactly 1 mile from both 1st and 2nd beaches, only 2 miles from downtown Newport and the mansions. Bring your bikes to enjoy the 14 mile trip from our front door to complete the Ocean Drive loop, or go the full 26.2 mile marathon loop. Whether your preference is to relax on the beach, enjoy Newport's shops, restaurants, & night life, or to cozy up inside, cook for yourself and watch a movie, this is the perfect retreat. *Please read full details.

Top guest favorite
A well-lit sleeping area features a spacious bed dressed in crisp white linens and a soft blue throw. A television is positioned on a dresser nearby, and a mirror reflects natural light from the window, creating an open atmosphere.
Apartment in Newport
5 out of 5 average rating, 118 reviews

Spacious Studio Near Cliff Walk

Prime location at the top of the hill between Downtown Newport & Easton's (1st) Beach. Run on the Cliff Walk - 3 blocks away! This private, open studio has a comfy memory foam king bed, new bath, kitchenette (microwave & fridge- no oven) & a big couch to stretch out on! Ideal for a couple looking to get away to somewhere a little more homey than a hotel. Has parking. Also suitable for parents and small child. NOTE: March 2026 front yard is muddy-ugly from construction, price reduced.😊NPT ID#755

Guest favorite
The inviting living area is bright and airy, featuring a mix of seating including an L-shaped sofa and two armchairs. Large windows allow natural light to illuminate the space, complemented by a neutral color palette and wooden accents throughout.
Home in Middletown
4.95 out of 5 average rating, 150 reviews

Coastal 4 Bedroom House - Steps from Beach

The Yellow Door Cottage is perfect for the ultimate beach vacation. This 4-bdrm house is close to restaurants/downtown/cliff walk and .3 mi to 1st beach! The main level offers open concept entertaining with kitchen, dining, living area, 1/2 bath and 1 bdrm. 3 spacious bdrms are located upstairs. Gather in the newly renovated lower level with wet bar, tv, games and a 3-piece bath. Enjoy the outdoor shower or sit around the fire pit. Ample outdoor space for lawn games in the fenced in back yard.

Guest favorite
A charming entrance to a tiny house is bordered by vibrant flowers and greenery. Two blue chairs provide a seating area by the door, complemented by potted plants. The wooden deck appears inviting and well-maintained, enhancing access to the home.
Tiny home in Middletown
4.98 out of 5 average rating, 168 reviews

Cozy coastal tiny house getaway

Situated on Easton's Point, brand new ocean front tiny house looks across to Mansion Row with access to a rocky beach for lounging, swimming, or fishing. The property is close to downtown Newport & ideally located between three beaches. The cozy unit has a queen bed, full bath & kitchenette with coffee maker, fridge, and toaster oven. There is a small deck with ocean views, access to ocean front, outdoor shower and off street parking. We provide beach chairs, a beach umbrella and towels.

Top guest favorite
A charming guesthouse is surrounded by lush greenery and vibrant flowers. A stone pathway leads to a welcoming entrance, framed by a large tree providing shade. The rustic design features rich wooden siding and a pitched roof, blending harmoniously with the tranquil landscape.
Apartment in Middletown
4.99 out of 5 average rating, 319 reviews

Lovely Private Setting, walk to beach.

A five minute drive to downtown Newport, and a few minutes walk to Sachuest Beach, this above-garage guesthouse is detached from the main residence with its own private entrance. There is a large living area and a kitchenette, bedroom and bathroom. The living room sofa converts to a bed, so the property is ideal for 2 people, however, the sleep sofa can accommodate 2 more. There is no extra charge for children under the age of 18. We are dog friendly. There's a $25 charge for a second dog.

Guest favorite
The rooftop space showcases comfortable seating arrangements with wooden furniture, offering expansive views of the surrounding neighborhood and distant ocean. Sunlight brightens the deck, emphasizing the inviting outdoor area. Green trees and colorful flowers can be seen in the vicinity, enhancing the landscape.
Apartment in Middletown
4.85 out of 5 average rating, 123 reviews

Spacious Newport Vacation Apt. w/Private Rooftop 2

GREAT LOCATION & SPACIOUS TOWNHOUSE! This location is unbeatable! 3 Bedroom apartment located right in the middle of First Beach (Easton's Beach - 0.7 miles) and Second Beach (Sachuest Beach - 1 mile). The only difficult decision will be which beach to go to! Do you want more than this? We got you! Free parking, Free Wi-Fi, Spacious Rooftop (Perfect for family gatherings, watch the sunset, view from Pell Bridge), HUGE backyard perfect for barbecues & full equipped kitchen!

Top guest favorite
A bright living room features a navy futon and a light-colored armchair, offering a cozy seating arrangement. Natural light filters through two white-curtained windows, illuminating the warm wooden floor. A simple white coffee table stands at the center, enhancing the inviting space.
Home in Middletown
4.98 out of 5 average rating, 120 reviews

Settle Inn-Cozy newly renovated house near beaches

Quaint, restful 1950's cottage located btwn two beaches within 2 miles. Located 1 mile from historic Newport. Two parking spaces on premises. Centrally located near restaurants, bars, grocery stores, breweries, and vineyards. Comfortable queen bed on level 2, full bathroom, fully equipped kitchen, grill, outdoor sitting & dining, air conditioners, washer & dryer, WIFI. Beaches chairs & towels available. Perfect for romantic couples getaway. Sorry, no pets.

Top guest favorite
The living space showcases a blend of rustic and modern decor. A cozy seating area, including a red chair, is positioned near a fireplace. A dining table with a striped runner and floral centerpiece complements the room's inviting ambiance, accented by warm natural light from the windows.
Guest suite in Middletown
4.92 out of 5 average rating, 856 reviews

Sunset Hill Idyllic In-Law Suite 5 min from Beach

3 beds = 1 queen and 2 twins for your group. ONLY a $10 cleaning fee from us! Our spot is PERFECT for attending summer weddings, especially at Newport Vineyards or Glen Manor! Avoid overpriced hotels and come get cozy at K & K's place. Enjoy walks on the BEST beaches (2nd & 3rd, avoiding red seaweed 1st beach). Find some peace and quiet amidst our serene setting, but just a stones throw from bustling Newport (avoid that congestion and the parking nightmare!)

Guest favorite
A spacious studio apartment features a light-colored sofa and a small coffee table in the living area. A queen-sized bed with white bedding is positioned near a wall art piece, while a kitchenette and dining area with bar stools are visible in the background.
Guest suite in Middletown
4.95 out of 5 average rating, 174 reviews

Unique and Modern Place to Stay!

Cozy studio downstairs from our ranch-style home. Includes kitchen (no stove), private bath, coffee setup, free parking, and WiFi. Great for a couple, solo guest, or family with a child. Quiet, safe neighborhood, 10 min from Newport crowd. Beaches nearby: 5 min to Easton Beach, 10 min to Middletown Second Beach. Note: Bathroom has a pump-assisted toilet. It works fine but the flush is a bit noisy. If you’re very sensitive to sound, this may not be ideal.

Top guest favorite
A recently renovated two-story home is featured with a gray exterior and white trim. Spacious porches overlook a well-maintained lawn surrounded by gravel. The entrance is marked by a set of wide stairs, leading to a welcoming front door flanked by large windows.
Home in Middletown
4.97 out of 5 average rating, 137 reviews

Steps from Beach and Minutes to Downtown!

Recently renovated home located between Newport's 2 best beaches. Choose your adventure! Spend the morning at Easton's (1st) Beach, soak up some sun, visit the aquarium, and ride the carousel. Grab a lobster roll for lunch before heading off for a stroll along Newport's Cliff Walk - or - Walk over to Surfer's End at Sachuest (2nd) Beach to catch some waves, sip on a Del's lemonade, and hike Sachuest Point National Wildlife Refuge.

Top guest favorite
Purple allium flowers bloom prominently in the foreground, while a light-colored two-story home is visible in the background. The house features a deck and a children's playhouse, with soft sunlight illuminating the scene.
Home in Middletown
4.86 out of 5 average rating, 151 reviews

Between Two Beaches - for Six and Family Sprawl

There is 2 night minimum through 2024. There are air conditioners in the bedroom windows and a portable unit in the living room. Towels, linens, soap, shampoo, wifi, tv, deck, grill, yard w/ swing set & kid's clubhouse - 1st & 2nd Beaches are nearby - Newport Center: 7 min by car. Groups of Unrelated Individuals: 22 & Older Only. NO EXCEPTIONS! Capacity: 6 adults with room for family sprawl (1-3 kids under 7)

Superhost
A cozy living room area features a fireplace with a golden frame, adorned with decorative items and a painting above depicting a serene landscape. A snow-dusted Christmas tree is placed beside a leafy plant in a ceramic pot, adding to the warm ambiance.
Guest suite in Middletown
4.86 out of 5 average rating, 206 reviews

Downtown middletown private suite - 5min Newport

Private entrance to the suite will not share any space with anyone . Free 2 parking lot. Sun- filled private suite with sofa bed and queen bed, fireplace, refurbished bathroom and living room. No local channels, tv works with your phone connected and free Hulu , Disney + channels. cooking kitchen, has Towel and Pots like kitchenware . Will not disturb the company. Quiet and perfect for couples!

Popular amenities for Middletown vacation rentals

When is the best time to visit Middletown?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR3,196 ZARR3,130 ZARR3,262 ZARR3,937 ZARR4,942 ZARR5,650 ZARR7,017 ZARR7,067 ZARR5,765 ZARR4,744 ZARR3,690 ZARR3,706 ZAR
Avg. temp-2°C-1°C3°C8°C13°C18°C22°C21°C17°C11°C6°C1°C

Frequently Asked Questions

  • Where should I stay in Middletown?

    Make yourself at home in Middletown by choosing from our most frequently booked neighborhoods. We have over 390 vacation rentals in Purgatory, over 2,080 vacation rentals in Newport East, and over 1,500 vacation rentals in Lawtons.

  • Are there vacation rentals with a dedicated workspace in Middletown?

    Yes! Work meets play with ease at over 780 vacation rentals in Middletown featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Middletown?

    Four-legged friends are welcome in Middletown. Choose from more than 400 vacation rentals for guests traveling with pets.

  • Are there Middletown vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 430 vacation homes with pools in Middletown, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in house rentals in Middletown?

    Experience the best of Middletown with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do condo rentals in Middletown have self check-in?

    Absolutely! We offer over 130 condo rentals with self check-in in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Middletown have wifi?

    Absolutely! We offer over 10 guesthouse rentals with wifi in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Middletown have a bbq area?

    Absolutely! We offer over 100 condo rentals with a bbq area in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Do hotel rentals in Middletown have a gym?

    Absolutely! We offer over 110 hotel rentals with a gym in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly resort rentals in Middletown?

    Middletown has more than 10 family-friendly resort rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about vacation rentals in Middletown

  • Total vacation rentals

    Explore 1,580 vacation rentals in Middletown

  • Nightly prices starting at

    Middletown vacation rentals start at R659 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 82,610 verified reviews to help you choose

  • Family-friendly vacation rentals

    970 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 400 rentals that welcome pets

  • Vacation rentals with a pool

    430 properties feature pools

  • Rentals with dedicated workspaces

    780 properties have a dedicated workspace

  • Wi-Fi availability

    1,580 of Middletown vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Middletown rentals

  • 4.8 Average rating

    Middletown stays are highly rated by guests—averaging 4.8 out of 5!

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