Holiday rentals with a pool in Lincoln County

RiverWalk Condo

Simple living here in Midcoast Maine at this peaceful, centrally-located, condo with in ground pool. Kitchen includes built in stainless steel microwave, dishwasher, and refrigerator. Enjoy indoor or al fresco dining on the deck (tables seat 4). A spiral staircase leads to a cozy living area serving as a studio, game room, or 2nd bedroom with Murphy bed. Both levels have decks with seasonal views of the water and amazing sunsets. Riverwalk Trail, behind the property, is a great spot to kayak.

Location · Family · Quiet

Shimmering River Retreat

Experience Shimmering River Retreat on historic Westport Island, Maine. This renovated riverfront log cabin and separate coastal cottage sit on the tidal Sheepscot River with 200 ft of frontage and a floating deep-water dock. The 4-bedroom, 2.5-bath main house features large deck, pool, and river views. The detached cottage includes a , bedroom and full bath. Sleeps 2–3 families. Kayaks, canoe, WiFi, linens provided. Private yard for games. Minutes from Boothbay Harbor, Wiscasset, and Bath.

2 Bedroom new renovation Condo/Pool/ River Access

Forget your worries in this spacious and serene space. Plenty of room for 4 with all new furniture, appliances, rugs and linens. An amazing space for a weekend or a month. Enjoy all the comforts of home in this special beautifully appointed 2 bedroom/3 bed private. Easy access to grocery, YMCA, Round top Ice Cream and some of the best restaurants in Damariscotta. Take in a nature hike to the Damariscotta River from your private path in the backyard. Free parking and beautiful pool in summer.

Family · Value · Air conditioning

Relax in this 3BR “Gem of a Stay” •Pool •Grill

Feels like home from the moment you arrive—clean, cozy, and thoughtfully prepared for a relaxing stay. Enjoy a spotless space with everything you need, plus extra touches guests consistently rave about. Unwind in a peaceful setting and take advantage of the heated pool, BBQ grill, and outdoor space perfect for families after a day exploring the area. Nestled on a three-acre lot in a quiet neighborhood, this apartment is attached to the host’s home near the town of Gardiner.

Family · Location · Indoor spaces

Tanager Cottage | 3BR + 2 Porches + Fireplace

Tucked along the woodland edge of Spruce Point Inn, Tanager Cottage welcomes families or groups with three bedrooms, 2.5 baths, and charming pine finishes throughout. From the double porches to the rolled stone fireplace and cozy living area, this Boothbay retreat blends warmth and function. Gather in the open spaces, stock the kitchenette, and recharge beneath forest-filtered light with the resort's full range of pools, spa, and activities just moments away.

Location · Hospitality · Nearby

Little Spruce Cottage | Wood Stove + Porch

Step into Little Spruce Cottage, a nostalgic woodland retreat tucked among towering trees at Spruce Point Inn. With cathedral ceilings and a cozy gas wood stove adding warmth, this Boothbay hideaway offers vintage charm and modern comfort. Perfect for couples or small families, the king and twin beds, efficiency kitchen, and tranquil porch set the scene for memorable Maine moments — with the resort's full array of amenities just a short stroll away.

House in the woods

Relax with the whole family at this peaceful place to stay. Quiet neighborhood. Open concept with pool and hot tub, big open lawn. Master bedroom-Queen Second bedroom- Full/Double Living room -large sectional Queen air mattress Possible sleep 8 The address is 34 Homestead Rd , but this app has it as fire road - it is the same ! I do have a business down in basement -hair salon- not typically an issue ( I try not to be open when I have guests)

Value · Location · Comfort

Oriole Suite | Stone Fireplace + Woodland

Set in a peaceful woodland corner of Spruce Point Inn, the Oriole Suite welcomes you with pine-paneled walls, a vaulted ceiling, and a cozy rolled-stone fireplace. This one-bedroom retreat blends rustic charm and modern amenities including a kitchenette and sleeping alcove with twin bed. Steps from the spa, forestside pool, and Lighthouse Hall, it's a tranquil escape designed for small families or romantic getaways in the heart of coastal Maine.

Pelican Cottage | 2 BR + Waterfront Porch

We can't wait to host you in our tranquil 2-bedroom Pelican Cottage at Spruce Point Inn in Boothbay Harbor! Perfect for friends or families, this charming retreat features a private covered porch with waterfront views, a gas fireplace, and beautifully decorated spaces. Step outside for whale watching, kayaking, or hiking, then return to the comfort of your cottage — with the resort's pools, spa, and on-site restaurants all just moments away.

Stay Together in Style

Gather in Comfort at The Flying Cloud Visiting for an event or getaway? The Flying Cloud offers space for your group—where everyone gets their own bedroom and bathroom! Relax in the swim spa and hot tub, share meals at the 14-person dining table, and enjoy games, TVs, and quiet spaces. Just a 5-minute walk to downtown Damariscotta, you’re close to shops, dining, and waterfront views. Book your stay today!

Location · Family · Layout

Luxury Condo on Water's Edge in Boothbay Harbor

Luxury condo with charm and character of a cottage. Private deck on water’s edge; dock/float shared with other 2 units. 2 bedrooms (each with a king bed) + den with trundle bed, 2 full bathrooms, modern kitchen. Sleeps up to 6. It's my home part of the year when not rented, so I've included just about everything you could imagine to make your (and my) stay comfortable.

Family · Location · Accuracy

Lovely 2 bedroom updated riverside condo with pool

Forget your worries in this spacious and serene private condo with access to the Damariscotta river and peaceful riverside trails. Bring your Kayak or paddleboard. Relaxing pool for you and your guests. Newly renovated with all new furniture, beds, bedding and kitchen supplies. Have your morning coffee on your choice of two spacious and private balconies.

Family · Value · Hospitality