
Pet-friendly holiday rentals in Oakland
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Oakland
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

Modern 1 Bedroom, Private Entrance, Great Location
This spacious and comfortable 1 bedroom in law suite will not disappoint! Equipped with its own entrance and parking, this modern suite is nestled in the Foothills of Maine, but within walking distance of UMF, restaurants, shops and just a short drive from Franklin Memorial Hospital. This space is perfect for business travelers and vacationers alike! Equipped with a full washer & Dryer, fully stocked kitchen, state of the art appliances and a luxury walk in shower. Pets welcome with deposit.

Luxury loft in historic downtown Farmington
Pets welcome! 25.00 pet fee required. A sanctuary in the middle of historic downtown Farmington, the Loft is the perfect jumping-off point for your Western Maine adventures. The kitchen is fully equipped with refrigerator, oven, and dishwasher, and all furnishings have been thoughtfully curated. Locally owned shops, restaurants, and UMF campus are steps away. It's the perfect home away from home for visiting professional, or those in town to visit family or student. See “Guest Access” section.

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak
Immerse yourself in our forest and serene pond. Quiet 40-acre commune consists of two tiny house cabins + barn on private pond. Book one of the simple yet elegant cabins/barn for more guests. Modern, off-grid, solar-powered retreat. Two solid glass walls to bring you closer to nature while staying in our simple yet elegant tiny house with all comforts of home. 5 min walk to shared fire pits, kayaks, pond & seasonal picnic shelter. AWD SUV or truck required. Off-grid, so no A/C. Pet fee $89.

Rustic Family Cabin on China Lake
This rustic cabin has been in my family for 4 generations. It's well loved, a bit quirky, sometimes musty and perfect for a family get away. We welcome well trained dogs, and have high expectations that you will respect the place and leave it in good shape for us and future guests. We welcome families, but after bad experiences, we are not available for your group of friends, reunion, or bachelor/(ette) party. We ask you to bring your own linens. The water in the cabin is not drinkable

The Cabin -Skowhegan
Main floor has living area, kitchen and dining area, 1 queen bed, with a daybed and trundler. Loft has 2 twin beds. The couch could be used as a bed, full bathroom. Has no kitchen sink but has a kitchen area with microwave, large air fry oven, fridge/freezer, toaster and coffee maker, iron/board. Also has TV, DVD/Blue ray player, Gas BBQ (May to November 1st.), as well as a picnic table, out door fire pit. For guest who are traveling by plane, towels are provided, upon request.

Downtown Augusta - 2 Bedroom - Newly renovated!
Located at the heart of downtown Augusta, this 2 bedroom apartment is a wonderful choice when visiting Augusta Maine with another couple or if you just want more room then your average hotel! This 2nd floor apartment comes fully furnished with brand new furniture, supplies and bedding! The apartment has keyless entry via a keypad with each guests receiving a unique pin. There is free parking and laundry available on site. Enjoy a stylish experience at this centrally-located place.

SILVER MOON, a Yurt for All Seasons
Silver Moon at The Appleton Retreat is quite private, check out the Trail Map. This contemporary yurt features a private therapeutic hot tub on the wrap around deck, a fire pit, and fast wifi. Silver Moon is located in a wooded area close to a bog that attracts a variety of wildlife. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

Charming Cottage With Spectacular Water View
Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

Brook Ridge Retreat
Work, play, & relax at Brook Ridge Retreat! Come visit your Colby or Thomas College student and have the comforts of home. Do some grilling or cook up a favorite meal in the full kitchen. Remotely connect to work or school at our custom-made desk and dedicated office area with wireless printer and available computer monitor. Splash in the brook or in the basin, and sit under the waterfalls. WiFi, firepit, Keurig or french press, electric fireplace, large decks, & big yard.

Hallowell Hilltop Home with Hot Tub & Sauna
Discover this newly renovated 2-bedroom, 1-bathroom home in a quiet family-friendly neighborhood in Hallowell. This home's rustic-modern design, natural light, and all-new amenities make it a perfect getaway. Relax in the hot tub, grill on the deck, enjoy the backyard or visit downtown Hallowell and explore its restaurants, cafes, live music and antique shops. This home is also minutes away from several hiking and walking trails that can all be found in our guidebook.

Lake-House on water, East Lake, Near Waterville
Welcome to the Lake House! 5 bedrooms. Access to a mooring. Full bathroom and kitchen with accessories. Bedrooms have locked doors & Wi-Fi. The house has a Deck and Docks, 8 foot by 10 foot floating Island, BBQ Grill. Lakeside Bon Fire Pit. Full bath, 30 feet from Lake! 2 entrances, 3 Kayaks, Fishing/Swimming. Nice neighbors including Camp Manitou, Matoaka and Somerset. Near Public Boat Landing & country store. I reside nearby, and will help with any issues.

Moore's place
🇺🇸🏳️🌈Our place is good for couples, solo adventurers, business travelers, families (with kids), big groups, and furry friends (pets). Close to hiking, Sugarloaf, ME IT Snowmobile trails is .03 miles away,located between Farmington, Skowhegan, and Augusta If your looking for someone to take you on a hike, and or short kayaking trip, pontoon ride around Lake Wassookeag. moose head lake on a Saturday or Sunday , (with a fee) just let us know
Popular amenities for Oakland pet-friendly home rentals
Pet-friendly house rentals

Cozy Winter Farmhouse Getaway

Classy AF Home, walk across the street to Colby!

Beautiful home on Wyman Lake

Spacious retreat in central Maine

Belgrade Lake house with Dock!

LUX Designer Private Waterfront Hot Tub - Secluded

Seaside House/Upstairs

The Riverfront Retreat - 27 minutes to Sugarloaf!
Pet-friendly home rentals with a pool

Large Home with Great View next to horse farm

Ski-In/Ski-Out Studio Condo w/ Après-Ski Comfort!

Luxe Liberty: Getaway with Heated Indoor Pool!

The Getaway - A River Paradise

Ocean View Retreat with Heated Pool / Hot Tub

SUGARLOAF, TRAILSIDE, 4-BDRM, & AC

Ski In Ski Out, Pet Friendly, Pool & Hottub Access

Home away from home
Private, pet-friendly home rentals

epicurean feast with zen like surroundings

Apartment in Skowhegan

Modern Tiny Cabin Near Belgrade Lakes

Cozy Lakefront Cabin * CampChamp

Lakefront cottage in Belgrade Lakes

Cozy Lakefront Retreat

Cozy Cabin with Lake Access

Peaceful 5 bedroom 4.5 bath waterfront house
Quick stats about holiday rentals that are pet-friendly in Oakland

Total holiday rentals
Explore 20 holiday rentals in Oakland

Nightly prices starting at
Oakland holiday rentals start at € 51 per night before taxes and fees

Verified guest reviews
Over 1,100 verified reviews to help you choose

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

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Oakland holiday rentals include wifi access

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

4.9 Average rating
Oakland stays are highly rated by guests – averaging 4.9 out of 5!
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