Pet-friendly holiday rentals in Gray

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

You will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular shops and restaurants. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, quiet hours after 10 pm. No parties. City of Portland License #: STHR-004465-2022

Pets · Outdoor spaces · Condition

The Purple House by Pettingill Pond

Welcome to Maine. The way life should be! The Purple House (bc the paint color is a happy shade of light purple) is 2 floor home ACROSS the gravel road from Pettingill Pond. Less than 100 ft away from the dock with SHARED access with two super friendly neighbors in the Summer. As a guest of this house you have access to this pond where it is perfect for swimming, rowing, kayaking, canoeing, paddle boarding, boating, floating, ice skating, & snow shoeing. Quick 5 mins from the city center!

Pets · Walkability · Decor

Spacious Freeport 5 BR Home | Near LLBean & Coast

Recently renovated and thoughtfully furnished Maine retreat with fast WiFi, smart TVs, spacious backyard fire pit, back deck with grill and outdoor dining, covered front porch, and plenty of room to relax with family and friends. Enjoy a large kitchen, dining room, and comfortable living spaces while feeling tucked away in nature, yet only 5 minutes from downtown Freeport, LLBean, breweries, restaurants, and shops. Bradbury Mountain State Park and Portland’s Old Port are nearby year-round.

Pets · Outdoor spaces · Indoor spaces

Cheerful spacious updated 1825 Maine Farmhouse!

Bring the whole family to this great place with lots of room for fun. Classic New England farmhouse in a quiet setting, yet minutes away from everything! Many updates ensure comfort while maintaining its original charm. House sits on 3 acres, located 5 minutes away from turnpike I-95. It’s just 30 minutes to Portland, Augusta, and Freeport! Close to Bates College, Lost Valley for skiing, a multitude of trails for hiking, swimming, breweries, restaurants & many activities for all ages!

Pets · Outdoor spaces · Nearby

On the water Boathouse!

In the water! Two story boathouse. Originally built in 1939 and parked boats in until 1972. Converted to living space in the early eighties. The upstairs consist of a bedroom walk in closet and a balcony. The downstairs is a living room, kitchen and bathroom. Walk out the door to the patio , dock , and beach! You won't find anything closer to the water! The balcony is the perfect place to watch the sunset, thunderstorms, or sip your morning coffee. Watch the fish out the window!

Outdoor spaces · Pets · View

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Outdoor spaces · Walkability · Check-in

New and Spacious Family Home Close to Sebago Lake

Full of light and thoughtful touches, this giant five bedroom home is perfect for your Sebago Lake getaway. Spend your evenings relaxing or entertaining on the spacious deck and days on the water. Perfect for family fun and couples' retreats, this home is a fantastic home base to explore the Sebago Lake Region. Enjoy a fully air conditioned home with mini splits in every room. Bedrooms include 4 King, 1 Full, and 5 Twin beds. Bathrooms include 2 walk in showers and one bathtub.

Walkability · Pets · Cleanliness

Best Ski & Lake House

Spectacular, expansive, state-of-the-art log cabin—your ultimate four-season escape. Winter ski trips (just 25 minutes to Pleasant Mountain, formerly Shawnee Peak), summer fun (beaches & watersports galore), & unforgettable year-round gatherings. Chef’s kitchen with two ovens, dining for eight + bar seating, sleeps up to 12 (with 2 king beds), two living rooms, and abundant outdoor dining & lounge space, including a playground - designed to make lasting memories!

Pets · Outdoor spaces · Beach

open concept Guest Suite in southern Maine

A short distance to many nature trails, Bradbury Mountain, state parks and the rocky coastline. This North Yarmouth guest suite is nestled between all the breweries and restaurants Portland has to offer as well as the famous outlet shopping in Freeport. We are located in a unique location where you are able to go from the rocky coast to the hiking trails all within 30 minutes. The guest suite is perfect for quiet lodging after a day of exploring or visiting.

Outdoor spaces · Walkability · Breakfast

Blueberry Hill

Beautiful property located on Watchic Lake in Standish Maine. Clear clean spring fed lake. 25 minutes to Portland with access to shopping, restaurants and entertainment. 45 minutes to North Conway New Hampshire. Where you wil find plenty of shopping, restaurants and winter skiing. Property includes use of Main Chalet home year round and two additional cabins each sleeping 4 are available from May-Oct. Great for extended families and friends.

Pets · Outdoor spaces · Hospitality

Rustic charm close to Portland

Peaceful and private. My home is a country getaway with unique charm and has a feeling like no other. Just voted the safest town to live in Maine, located close to downtown Portland, the Portland Jet Port, Freeport, beautiful Maine beaches, apple orchards, a Gorgeous wedding venue a mile away called Caswell Farm and close to trails for hiking, my home has many options. It's a great spot for a group of 6 or a couple of 2 to unwind.

Walkability · Outdoor spaces · Quiet

Sebago Lakehouse: Hot Tub and Private Beach Access

Lovely 3 bedroom/2 bathroom house in the woods with a Hot Tub and access to the private shared beach! Sebago Lake is a perfect family destination for swimming, boating, and fishing. It is ideally located for a day trip to Portland, Old Orchard Beach, Kennebunkport, or Freeport. Or stay home, enjoy the Lake or watch the stars from the Hot Tub. Close to grocery stores and restaurants. Lake and beach access is only a 5-minute walk.

Outdoor spaces · Pets · Comfort