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Holiday rentals in Litchfield

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Top-rated holiday rentals in Litchfield

Guests agree: these stays are highly rated for location, cleanliness and more.

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Cottage

4.91 out of 5 average rating, 85 reviews

Tranquil waterfront cottage

A private clean tranquil cottage, dock, parking, deck, grill, hammock, kitchen & all amenities, bathroom, 2 bedrooms, sleeps 5, futon, WIFI, cable, bidet, washer & dryer, granite outdoor table, kayaks, paddle boards, floats, fire pit and fireplace. Minutes from great restaurants, bars, hiking trails, and shopping. The most amazing sunsets. 30 minutes from Portland. Winter rentals as well. 40 min. from Shawnee Peek, 1 mile from Seacoast tubing. This place is privately yours. Smoke free please!

Cabin

5 out of 5 average rating, 17 reviews

[B] The Bellemark | Lakefront Cabin + Amazing View

Welcome to The Bellemark Lakehouse! Our Lakefront Log cabin located in Fryeburg Maine, is the perfect spot to relax and escape the busy world. Located only minutes from Pleasant mountain and downtown Fryeburg, it is the perfect jumping off point for any season. Our open concept living area/kitchen caters perfectly for gathering after a long day on the lake or slopes. Light a fire, sit back & enjoy the breathtaking views of the mountains and lakes in the winter or hang on the porch in the summer!

Guest favourite

Home

4.93 out of 5 average rating, 118 reviews

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Guest favourite

Guest suite

4.93 out of 5 average rating, 56 reviews

Mystery Mountain View Near many outdoor activities

Put up your feet at this 900 sqft rental unit with 1 large bedroom, full kitchen, media room, sitting room, full bath, dining area, and dart board. Private entrance, daylight basement in lower level of our home. There is a key code box to obtain access, and guest parking. 15 minutes to Sunday River and Black Mountain and 20 minutes to Mt. Abram ski resorts. Swimming access at Howard Pond. Skiers, riders, hikers, kayakers, and outdoor enthusiasts would love this location anytime of the year.

Guest favourite

Cabin

5 out of 5 average rating, 12 reviews

All seasons Lake House next to ski areas

Welcome to the Howell’s cabin ! A beautiful and peaceful lake house in the heart of Maine. Located just 5 minutes from Mt Abrahm ‘s ski area , 20 minutes from Sunday River Ski Center, and 15 minutes from Bethel, a charmy town with great restaurants and unique attractions. This has been our family getaway for nearly 40 years. Recently renovated, fully equipped kitchen, tiled bathroom, heating/ AC system, Wi-Fi and a nice deck to enjoy your morning coffee. No suitable for infants under 6

Guest favourite

Home

4.83 out of 5 average rating, 6 reviews

Tailwinds - Upscale Oceanfront! Stunning Views!

Welcome to Tailwinds in East Boothbay, where you will enjoy stunning sunsets over Linekin Bay from the comfort of this beautifully updated home. Formerly a B&B, this is a perfect place to gather frinds and family with en-suite baths 2 living rooms and a large porch. You will also find all new beds and furniture, luxurious 100% cotton linens, and AC window units in the bedrooms. Located between downtown Boothbay Harbor and Ocean Point, this is a gorgeous spot for your next family vacation!

Guest favourite

Flat

4.94 out of 5 average rating, 17 reviews

Boho Beach Escape: Top-Floor Condo

Soak up the sun at our charming Old Orchard Beach retreat! Just steps from the sand, this spacious beach house is perfect for families. Enjoy ocean breezes and on-site fun after a day at the beach. Explore nearby arcades, shops, and restaurants. Comfy beds and a relaxing atmosphere await you! Our peaceful haven is nestled away from the hustle and bustle yet close to attractions. Enjoy cozy beds, a nostalgic record player, plush robes, an OLED smart TV, and sound machines in the bedrooms.

Guest favourite

Home

5 out of 5 average rating, 5 reviews

Stunning Beachfront Dream Home

Experience ultimate luxury at this newly built (2023) beachfront home, featuring breathtaking ocean views from nearly every room. With high-end finishes, two gourmet kitchens, and a spacious living area, every detail is designed for your comfort. An elevator provides easy access to all three levels. Fully furnished for a turnkey stay, relax as soon as you arrive. Don’t miss the chance to stay in this dream home—perfect for creating unforgettable memories with friends and family!

Guest favourite

Home

5 out of 5 average rating, 6 reviews

2BR Lake House on Private Beach w/hot tub & sauna

Romantic getaway or peaceful family vacation, this lake house is right on a private beach, and perfect all year round!The beach is literally your back yard! Experience beautiful views while enjoying a cozy outdoor fire. Relax and take amazing sunset pics in the covered hot tub, or unwind indoor w/the sauna and fire place. Cook up a delicious meal in the fully stacked kitchen. Centrally located near hiking trails, and 45min from North Conway outlets. Book now and make memories! ✨

Townhouse

4.89 out of 5 average rating, 9 reviews

Unit 3 Getaway - Perfect for Families!

Unit 3 **Have a large group ask us about renting all 3 units sleeps 22** This 2 bedroom, 2 bath unit has been completely renovated. Only steps to the beach, this basement unit is literally just one block away from public beach access, and will sleep up to 6 people. Off-street parking, private picnic area and large gas BBQ grill. You will need to bring your own sheets, pillow cases and towels. Check in Saturday after 3PM, check out the following Saturday by 10AM.

Guest favourite

Home

5 out of 5 average rating, 58 reviews

Dream Vacation Home - Full Amenities & Hot Tub

The Bingham House in Bethel / Sunday River is the ultimate vacation home to meet all your needs. Sleeps up to 18 people in 6 bedrooms, 6 bathrooms. Full service amenities include: wifi, 10 HD TVs with premium cable (including HBO), 8-person hot tub, fire pit, billiards room, bar w/ wine fridge, game room, elevator, full kitchen & walk-in pantry, gas grill, fireplaces, parking, free shuttle to Sunday River, crib + high chair + booster seat

Guest favourite

Home

4.86 out of 5 average rating, 14 reviews

Peaceful Sun and Fun Cabin-B

Your well needed relaxing and peaceful getaway awaits in this newly renovated cabin centrally located on a quiet safe street with short walk to the beach, restaurants, and Pier and amusements. This newly renovated 1-bedroom cozy cabin is perfect for a those looking to spend a peaceful and lovely time near the white sand in Old Orchard Beach. There is a hiking trail and biking trail beginning at the end of our street.

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Popular amenities for Litchfield holiday rentals

Free parking on premises

Air conditioning

Stay near Litchfield's top sights

Theater at Monmouth18 locals recommend

Grateful Grain Brewing Company12 locals recommend

The Milkhouse Farm & Dairy9 locals recommend

Apple Valley Bakery6 locals recommend

The Meadows Golf Club5 locals recommend

South Monmouth Market5 locals recommend

Other great holiday rentals in Litchfield

Guest favourite

Cottage

5 out of 5 average rating, 103 reviews

Lakefront Home, Sandy Beach, Belgrade Lakes Maine

Guest favourite

Home

5 out of 5 average rating, 6 reviews

The Hideaway, In Harpswell Maine

Guest favourite

Home

4.97 out of 5 average rating, 63 reviews

cozy 3 bedroom ranch with deck and screen porch

Home

4.75 out of 5 average rating, 20 reviews

Log Cabin *15 acres*hunting* snowmobile*skiing

Guest favourite

Home

5 out of 5 average rating, 100 reviews

Waterfront Farmhouse with Modern Flair!

Guest favourite

Home

4.98 out of 5 average rating, 89 reviews

Woods Lane Golf and Beach Vacation

Guest favourite

Cabin

5 out of 5 average rating, 7 reviews

Great Pond Getaway|Lakefront|Dock|Sunset Views

Guest favourite

Cabin

4.95 out of 5 average rating, 100 reviews

Cabin on the hill!

Destinations to explore