Holiday rentals in Middletown

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Top-rated holiday rentals in Middletown

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

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Top guest favourite
A manicured outdoor space features a grassy lawn framed by vibrant flower planters. Lounge chairs are positioned for relaxation, and a cozy seating area invites gathering. Natural stone pathways lead to a covered porch with wooden pillars, creating an inviting connection between the indoor and outdoor environments.
Home in Middletown
4.99 out of 5 average rating, 170 reviews

Walk to the Beach - Serene Coastal Country Cottage

Relax with ocean breezes. A 13 minute walk to pristine second beach and a short drive to everything Newport has to offer. Recently refreshed, and nestled within the famous Paradise farm setting, this home will keep you perfectly comfortable amid your Island exploration downtime. A full kitchen with Gas range and beautifully kept grounds will allow for alfresco summer dining. The home is Immaculately kept and spaciously sleeps max 6 adults and 2 children under 13yrs for a maximum of 8 guests.

Top guest favourite
An aerial view of a modern, three-level home features a spacious outdoor deck with seating arrangements. Large glass doors on each level allow natural light to flood the interior. A well-maintained lawn surrounds the structure, and neighboring homes are visible in the background.
Home in Middletown
5 out of 5 average rating, 104 reviews

Your 5 Star Beach House Experience

Only 1 week left for Summer 2026! 🌊☀️ Just 60 seconds from Easton's Beach, Mar Azul is your perfect Newport getaway! Nestled in Easton’s Point, this stunning 3-level modern home puts you steps from downtown Newport’s vibrant attractions, dining, and charm. Unwind with a cocktail on our ocean-view decks, fire up the BBQ on the private patio, or stroll to the beach and restaurants. Book now for an unforgettable summer escape at Mar Azul. ///Smoking & Parties are not allowed: RE.00887-STR

Top guest favourite
A hot tub is situated under a shaded gazebo, surrounded by lush greenery and blooming hydrangeas. The area is well-maintained with neatly trimmed grass and subtle outdoor lighting, creating a serene space for relaxation.
Home in Middletown
4.98 out of 5 average rating, 102 reviews

Coastal Hideaway- hot tub close to Newport+beaches

Welcome to The Coastal Hideaway! Just off Indian Avenue within walking distance of Pebble Beach, your friends or family can relax by lounging on the outdoor patio, rocking on the side porch, or soaking in the hot tub. You can also enjoy the local beaches, visit Sweet Berry Farm, taste the local cuisine, and enjoy the many artisan shops in downtown Newport (just 15 minutes away). Brand new listing, this home is well equipped with everything from beach chairs to a pack-n-play to a chef's kitchen.

Top guest favourite
A cozy living area features a spacious sofa with decorative pillows, accompanied by a side table and a lamp. Light streams in through large windows, and a dining table set for six is visible in the background. Soft blue walls enhance the inviting ambiance.
Townhouse in Middletown
4.97 out of 5 average rating, 143 reviews

Cozy townhouse w/yard, 1 mile to beach & downtown

Bright 2 level townhouse with remodeled bathroom in July 2024 & refinished hardwood floors as of Oct '23. Tastefully decorated & stocked w everything you need! Kitchen w/ gas stove, micro, toaster & Keurig coffeemaker. Master bdrm w/ queen bed & TV; 2nd bdrm has full size bed. Gorgeous sunporch overlooking a nice shared yard w/ chairs, table & gas grill. Driveway for 3 cars. Quiet area centrally located, very close to beaches 🏖 & the hopping restaurant row of Lower Broadway & downtown Newport!

Top guest favourite
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
4.99 out of 5 average rating, 154 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 favourite
Guest suite in Middletown
4.95 out of 5 average rating, 362 reviews

Traveler's Guest Nest, special winter rates

Off-Season Special – Cozy Coastal Getaway Near Newport Escape the crowds and experience Newport in its quiet season. Our private studio offers peace, comfort, and easy access to the area’s best trails and beaches, just 3 miles from downtown. Perfect for a weekend getaway, nature walks, or a cozy couple’s retreat. Features: • Private entrance & patio • Easy parking • Quiet+safe Special off-season rates for fall and winter stays. A perfect little escape by the sea, without the Newport prices.

Top guest favourite
A bright and spacious kitchen is equipped with modern stainless-steel appliances, including a refrigerator and double oven. Marble countertops are complemented by natural wood accents. A center island offers additional prep space, while elegant pendant lights hang above, enhancing the inviting atmosphere.
Home in Newport
4.95 out of 5 average rating, 117 reviews

Downtown Cottage

Experience refined coastal living in this exquisitely designed downtown Newport retreat, where luxury and comfort are seamlessly blended. Thoughtfully furnished with high-end, organic materials—from linen bedding to natural wood accents—every detail is chosen for both elegance and well-being. The open-concept living area flows into a chef’s-grade kitchen, outfitted with premium appliances, a gas range, and artisan cookware perfect for preparing locally sourced seafood or entertaining with sty

Top guest favourite
The exterior of the house features a large deck made of wood, surrounded by a spacious lawn. A fenced yard provides privacy, while multiple gabled roofs and windows enhance the architectural character of the home.
Home in Middletown
4.99 out of 5 average rating, 186 reviews

Beach House

My place is: -less than a 5 min walk to First beach -15 min walk to Second beach. -1 mile walk/drive to the start of the cliff walk. -2 miles to downtown Newport. You’ll love my place because of the: -Two Primary Suites -Open concept living -Huge outdoor entertaining area -Super close to beaches, cliff walk and a quick drive to downtown. . -Brand new construction. My place is good for 2 couples, large families (with kids), and big groups. RI Registration # RE.000311-STR

Guest favourite
A spacious deck is visible, providing a view of the surrounding rooftops and the harbor in the distance. Sunshine illuminates the scene, accentuating the blue sky dotted with clouds. The distant water adds a tranquil aspect to the urban landscape.
Flat in Newport
4.92 out of 5 average rating, 166 reviews

Penthouse harbor view. 30 steps

Penthouse apartment overlooking Thames St. and the Harbor w/ a huge deck. Please take notice this a third floor apartment. Located in the heart of Newport right on Thames St. Cook dinner in the chef style kitchen and eat al fresco on the deck. The central location gives you walking distance to dozens of shops and restaurants as well. It is a 15 min. walk to first beach and the mansions. A private parking space is included with the stay making it super convenient.

Guest favourite
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, 837 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!)

Top guest favourite
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.
Flat in Middletown
4.99 out of 5 average rating, 315 reviews

Lovely private setting near 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.

Guest favourite
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, 197 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 holiday rentals

When is the best time to visit Middletown?

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Avg. price$250 SGD$245 SGD$255 SGD$308 SGD$387 SGD$442 SGD$549 SGD$553 SGD$451 SGD$355 SGD$284 SGD$258 SGD
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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 1,500 vacation rentals in Lawtons, and over 1,980 vacation rentals in Memorial Boulevard.

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

    Yes! Work meets play with ease at over 810 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 380 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 400 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 serviced apartment rentals in Middletown?

    Experience the best of Middletown with our serviced apartment rentals, starting at about $230 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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 house rentals in Middletown have self check-in?

    Absolutely! We offer over 200 house rentals with self check-in in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Middletown have a bbq area?

    Absolutely! We offer over 50 apartment rentals with a bbq area in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Middletown have a gym?

    Absolutely! We offer over 30 apartment rentals with a gym in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly townhouse rentals in Middletown?

    Middletown has more than 20 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about holiday rentals in Middletown

  • Total holiday rentals

    Explore 1,640 holiday rentals in Middletown

  • Nightly prices starting at

    Middletown holiday rentals start at $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 81,270 verified reviews to help you choose

  • Family-friendly holiday rentals

    940 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 380 rentals that welcome pets

  • Holiday rentals with a pool

    400 properties feature pools

  • Rentals with dedicated workspaces

    810 properties have a dedicated workspace

  • Wifi availability

    1,630 of Middletown holiday rentals include wifi 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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