
Vacation rentals with a pool in Middletown
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Middletown

Total vacation rentals
Explore 480 vacation rentals in Middletown

Nightly prices starting at
Middletown vacation rentals start at $112 CAD per night before taxes and fees

Verified guest reviews
Over 5,480 verified reviews to help you choose

Family-friendly vacation rentals
270 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 80 rentals that welcome pets

Rentals with dedicated workspaces
280 properties have a dedicated workspace

Wifi availability
480 of Middletown vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Middletown rentals

4.7 Average rating
Middletown stays receive an average rating of 4.7 out of 5 from guests
Top-rated rentals with a pool in Middletown
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Perfect Coastal Escape close to Newport & Beaches!
Located in Portsmouth's desirable Lilac Lane neighborhood, and conveniently located between downtown Newport and Bristol, this beautiful home offers everything you're looking for! Enjoy the sunset as you relax and unwind in privacy on the back deck or by the pool. You'll be surrounded by landscaped gardens and sweeping picturesque farmlands. 6 miles from Historic Newport and Middletown beaches, 2.4 miles from Sandy Pt. Beach, 8 miles from Bristol, and a short drive to many local vineyards!

Close to Town, Beach & Vineyards! Pool!
Welcome to your ideal coastal retreat. This spacious 4-bedroom, 2-bath home comfortably sleeps up to 8 guests and blends modern amenities with an unbeatable location. Just minutes from wineries and local beaches, the home is perfect for relaxing and recharging. Enjoy a gated backyard featuring a private pool (open mid-Jun through mid-Sept), fire pit, and a beautiful deck with BBQ grill. Inside, you’ll find a well-equipped kitchen and generous living spaces designed for comfort and connection.

Bass Rocks Upper Decks apartment
With 10+ years of STR history with a 5 star rating, Bass Rocks Upper Deck is new to Airbnb. This spacious loft is located in a large historic carriage house that was remodeled into 3 apartments with privacy in mind. Just 5 minutes' drive to downtown Newport and a short walk to Sachuest (Second) Beach, it has one of the best locations in the Northeast! The beautiful mile of public beach only 1500 feet away is the best in town for sun bathing, swimming, or surfing at legendary Surfer's End.

Dwntwn 1BR/Pool/Gym/Parking/Hi-Speed WiFi/King Bed
Just steps away from everything that downtown Providence has to offer is our beautifully furnished upscale apartment with a view of the city & courtyard. This space offers a large fully equipped kitchen, king size bed, high speed internet, 55" smart TV w/Disney+ & Netflix. The building has a fitness center, heated lap pool, BBQ & picnic area, a concierge, resident lounge & covered parking. No car needed, we are just a short walk to all shops, restaurants, the mall & amazing Waterfire!

Private POOL, Central AC, Walk to beach, king MBR
Summer 2025/2026 full weeks run SUNDAY to SUNDAY. Max capacity: 8 adults, 4 kids under 12. Spacious 4-5BD/2BA, close to downtown Newport, walk to beach, fully fenced private backyard and OWN POOL. Newly remodeled KITCHEN. King bed master BD. Great family neighborhood. Good fit for families, weddings/reunions, kids. CENTRAL AIR. Easy secure check in with private 4 digit code; No keys to lose! Minutes walk to the Atlantic Resort. Walk to Newport's best beaches and many restaurants.

Get comfy in the country!
This special place is close to everything, making it easy to plan your visit. Just 10 minutes away from town. Secluded cabin on a 57-acre farm outlooking a large paddock with 4 highland cows. This beautiful property has a neighboring golf course and trails connecting to Heritage Park. Pool. Fireplace. Amazing sunsets! Who wouldn’t want to live like Yellowstone for a little? Home of Welcome Pastures, a Nonprofit 501(c)3 organization. Portion of proceeds go towards the foundation.

Jamestown:Coastal Cottage in town near beach/Nwp
The cottage is a perfect getaway in the Ocean State. It is an ideal location within walking distance of restaurants, shops, local beaches & parks. The renovated chef's kitchen is an entertainer's delight. This 3/2 home has two living rooms and high-speed internet allowing for ample work and play. The private outdoor deck features a hot tub (open during the winter), pool, fire pit, BBQ, gazebo, multiple seating areas, and a backyard for additional recreational space.

Artist studio in the woods
Take it easy at this unique and tranquil getaway. Be a little bohemian, stay in an artist’s studio for two adults, views of woods and stone walls.walk along a 300 stone wall past a 5000 gallon koi pond, and discover a stone sculpture in the woods. Wall of windows, private deck, queen size bed, kitchenette, full bath, dishwasher, Wi-Fi, cable tv, guest robes, iron and board, kuerig, all necessary utensils. Quiet, tranquil, relax. 47 minutes from Gillette Stadium.

Private Heated Pool • Upscale 4BR • 13 min 2 Beach
Enjoy a private heated salt-water pool, spacious living areas, and dining for ten — perfect for families and groups looking for comfort, privacy, and easy access to beaches, mansions, and downtown Newport. Relax in your own private oasis just minutes from Newport. Welcome to #ChiquitaCasita, a thoughtfully designed 4-bedroom home offering the space, comfort, and amenities guests want — without the congestion or parking challenges of downtown Newport.

Newport 3BR Long Wharf Waterfront Resort
The Long Wharf Resort managed by Wyndham is located on the picturesque waterfront bordering downtown Newport. Venture out from your suite and explore the vibrant Thames Street where you'll discover a wealth of coffee shops, antique stores, art galleries and live music entertainment. A variety of Newport attractions and things to do are within walking distance from this premier waterfront vacation resort in the heart of beautiful Newport.

Townhouse Close to Downtown Newport & Beaches
Two bedroom townhouse in residential neighborhood; 1 mile from historic/downtown Newport (shops/restaurants); 2 miles from Easton's Beach; 2 playgrounds within walking distance; above ground pool, fire pit, 20' furnished deck, grill; plenty of parking; WiFi & apps; central air. It's about a 7 minute uber ride to downtown Newport or Easton's Beach. Shaws/LQ/Starbucks/Dunkin are one mile away in the opposite direction.

Beachfront W/ Hot Tub, Sauna, Pool & Panoramic View
Welcome to the Heart of Somerset! Read our reviews & stay a while! Nestled at the very tip of Somerset on a private dead-end road, this coastal waterfront home is the perfect place for a family retreat, romantic getaway or friends seeking adventure Marvel at the panoramic views and dramatic colors from Sunrise to Sunset. Grab a kayak, or sit back and relax and let the gentle sea breeze wash your worries away!
Popular amenities for Middletown rentals with a pool
House rentals with a pool

Lake Tiogue retreat

Cozy Coastal Escape in Warren | Dog Friendly

Family-Friendly Beach Getaway

Minimal Modern Home Getaway

Mid-Cent Artist Cape, Pool, 3B, Beaches, 22 Acres

Vitamin Sea Pier Beach House POOL. Book Fall 2026!

Oyster Hill

Three bedroom home with pool, dogs considered
Condo rentals with a pool

Newport Oceanfront Resorts

Wyndham Inn on Long Wharf |1BR/1BA King Bed Suite

Wyndham Long Wharf Resort |2BR King Suite

Timeshare Rental. 3rd floor Condo w/ water view

2BR Newport Oceanside Condo Resort w/2 Pools!

Newport Resorts

Wyndham Inn on Long Wharf |1BR/1BA King Bed Suite

Newport Downtown Rental
Other vacation rentals with a pool

Hot Tub/Pool/FirePit Near NFL Gillette/Xfinity/PVD

Vineyards, Newport, Narragansett, In-Ground Pool

NEW ENGLAND SEAPORT ESCAPE in our 2 Bedroom Deluxe

Modern, Bright, Private Studio w/POOL

The Denison Markham Carriage House

Boutique Luxury Waterfront w/Pool & Sunset Views

Newport Long Wharf Resort 7/31/26-8/7/26

Private suite-2 bed/2 bath, pool/ hot tub access
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $175 CAD | $186 CAD | $205 CAD | $273 CAD | $316 CAD | $453 CAD | $611 CAD | $653 CAD | $641 CAD | $289 CAD | $181 CAD | $181 CAD |
| Avg. temp | -2 °C | -1 °C | 3 °C | 8 °C | 13 °C | 18 °C | 22 °C | 21 °C | 17 °C | 11 °C | 6 °C | 1 °C |
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- Gillette Stadium
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