
Apartment holiday rentals in Cumberland
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Top-rated apartment rentals in Cumberland
Guests agree: these apartments are highly rated for location, cleanliness and more.

Quiet Comfy Victorian Escape
Spend your vacation, work-trip, or weekend getaway in this lovely renovated cozy 2 bedroom unit. Apartment 2 is located on the second floor of a three family house where you have access to all the modern appliances: refrigerator, W/D, microwave and TV in the living room. A brand new queen bed each bedroom, with seat in cozy seating in the living room. Located in the very central Oakdale neighborhood, this unit is steps from Deering Park, Sea Dogs stadium, USM Law School and Portland's Old Port.

Peaceful Oasis on Munjoy Hill -2nd flr/3BR+parking
Spacious, light-filled 3 Bedroom/1 bath 2nd-floor apartment with tasteful art, contemporary furnishings, + a well-appointed kitchen. Fantastic location! -A 5-minute walk to the Eastern Promenade with its food trucks, beach & scenic trails -Nearby are bakeries, cafes, world-class restaurants and popular breweries -Relax in the serene garden w/ outdoor seating -A 15-minute walk takes you to the Old Port. Discover the best of Portland, then return to A Peaceful Oasis, a place to truly call home.

Falmouth Waterfront Carriage House Apt
Waterviews! This 1 bedroom apt has a new “purple”mattress, above our detached garage in classic Maine waterfront neighborhood. Next door to the iconic Town Landing Market and Town Landing pier/beach. In beautiful Falmouth Foreside neighborhood. Walkable to Dockside Restaurant and marina, and 10 minute drive or bus to downtown Portland. 20 minute drive to Freeport shopping. We only accept well- behaved and house- trained dogs, no other pets are allowed for a fee of $75.00 per dog per stay.

Sweet 1-Bedroom Apartment in Vintage Village Cape
Built roughly 200 years ago, the traditional cape housing this first-floor apartment is located on a hilltop above the Royal River, just steps from restaurants, trails, and waterfront. It's been thoroughly renovated, and features pretty much all the comforts of home—including a full kitchen with dishwasher, a wood-burning fireplace insert, an all-natural mattress (super comfy), and a clawfoot tub-equipped bathroom. Oh, and if you're bringing a third, let me know—and I'll roll in the rollaway.

RETRO BnB in the Heart of East End Portland
Retro BnB in The Heart of Portland's East End offers a combination of 70's mod charm with a vibrant comfortable style. Sunny, first floor back apartment with private entrance, one hybrid coil/thermarest queen bed overlooking yard with lovely perennial garden, bathroom with central, well appointed kitchen/dining room. This space is perfect for one couples looking for a cozy home base hideaway. A short walk to gourmet restaurants, cafes, East End beach and all Portland peninsula has to offer!

Sopo Abode
Welcome to your garden oasis. Your home away from home. This elegantly styled garden level apartment in South Portland's crown jewel neighborhood, Sylvan Sites, is spacious, calm, and inviting. Have a sit in your private sauna, and take in the abundant birdsong of the neighborhood from your private back patio while you sip your morning coffee. Just down the road (5 minutes) to downtown Portland, Willard Beach, or Knightville, and 10-15 minutes to Scarborough and Cape Elizabeth beaches.

Peaks Island Master Bedroom Suite
Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.

Harborview - Curated East End Escape w/ Parking
Harborview is a newly renovated, top-floor apartment perched on the edge of Munjoy Hill in Portland's East End. This home is a short stroll to the Eastern Promenade and the East End Beach, the Casco Bay Islands Ferry Terminal, and the historic Old Port. The apartment features a spacious open kitchen, dining, and living room floor plan adjoined by a large private deck. It's the perfect spot to gather, relax, and dine while enjoying the breathtaking views of Casco Bay!

Private Hill Top Apartment/w One Car Driveway
Cover photo is a view of Eastern Prom, a 5 minutes walk. Two bdrm apartment. 1 Queen, 1 full. Private entrance,sitting room/kitchenette w/sink, fridge , toaster & microwave. Bath w/tub&shower, Up to four adults, children and infants welcome. Rate based on two adults. A $30 up charge per night for each additional adult, 4 maximum. Pet(s) not to be left alone in the apartment. $60 charge per pet,per night. Babysitting available by arrangement. Note: No TV.

Cozy King bed apt near Portland with free parking
Enjoy a comfortable and relaxing getaway in this charming second-floor studio, owned and operated by a local family. Nestled in a quiet neighborhood, yet just minutes from Downtown Portland with easy access to I-95 and I-295, it offers the perfect mix of peace and convenience. This cozy studio features a brand-new King bed with a fresh mattress and pillows, along with a 3/4 bath—perfect for unwinding after a day of exploring the city or coast.

2 Bedroom Just Steps from the Old Port w/ Parking
Whether traveling for work or pleasure, our apartment is the perfect spot to call home in the heart of downtown Portland. It's steps from the Merrill Auditorium and 6 or less minute walk to the Old Port, One Monument Square, restaurants and shopping on Exchange St, and much more. Features of this 2nd-floor apartment include off-street parking, two bedrooms, living room with TV, newly renovated bathroom and kitchen, and coffee bar.

Peaceful & Cozy Falmouth Getaway
Relax with the whole family at this peaceful home away from home. Enjoy our brand new one bedroom apartment above a detached garage. There is a convenient private key coded entrance. We are located in West Falmouth situated about 5 miles from downtown Portland, a great home base for exploring Maine's towns, beaches, mountains and more!
Popular amenities for Cumberland apartment rentals
Weekly apartment rentals

Portland + Cape Elizabeth + Beaches + luxurious!

Munjoy Hill House - Pet Friendly !

Comfortable studio apartment in quiet location

Crow's Nest

Modern Studio Loft w/ Parking in Perfect Location

Amazing Views! Perfect Location. Loft style feel.

Quiet West End Retreat - parking - 100% Non Smoker

Updated stylish 1 BR Downtown Apt
Private apartment rentals

Urban Seaside Retreat- East End Overlook Casco Bay

Lovely 4 Bedroom with free parking

Spacious 1st floor New England charm.

Cozy new unit in charming town near Portland

The Nest

The Inn on Bridge Street

Cozy Urban Treehouse on Munjoy Hill

Midcentury Modern 2 Bedroom Village Oasis
Apartment rentals with a hot tub

3 bed up apt with no cleaning fee or checklist

Falmouth 3br near Town landing

Welcome to our BoHo Treehouse!

Cozy hot tub haven

Downtown Hideaway-Loft HotTub Modern Clean Private

Saco/Old Orchard Beach Get Away

Beautiful West End studio, hot tub, free parking

Maine Hacienda w/hot tub & seasonal pool
Quick stats about flat rentals in Cumberland

Total holiday rentals
Explore 20 holiday rentals in Cumberland

Nightly prices starting at
Cumberland holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 1,040 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Cumberland holiday rentals include wifi access

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

4.9 Average rating
Cumberland stays are highly rated by guests – averaging 4.9 out of 5!
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- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Scarborough Beach
- Popham Beach, Phippsburg
- York Harbor Beach
- Popham Beach State Park
- Pemaquid Beach
- Cranmore Mountain Resort
- Willard Beach
- King Pine Ski Area
- Short Sands Beach
- Cape Neddick Beach
- Pemaquid Point Lighthouse
- Gooch's Beach
- East End Beach
- Diana's Baths
- Funtown Splashtown USA
- Crescent Beach State Park
- Coastal Maine Botanical Gardens
- Pleasant Mountain Ski Area
- Footbridge Beach
- Wolfe's Neck Woods State Park




