Location

Dates

Guests

Vacation rentals in New Gloucester, Maine, United States

Welcome to the Guest House!

The guest house is your own separate place, tucked in among the surrounding gardens and trees on Munjoy Hill.

Entry and dining area with sliding door connecting to guests' private garden patio.

Living room with side tables and big window for afternoon sunlight.

Radiant concrete slab heat on the ground floor for warm toes in winter. Radiant tile heat in the upstairs bathroom.

Modern Guest House + garden patio on Munjoy Hill

2 bedrooms·1½ baths

Portland • Maine

4.98(55 reviews)

$1,745.09 USD total for 4 nights

Oct 3 – 7, 2026

Free cancellation

Modern Comfort: Game Room & Access to Portland

Modern Comfort: Game Room & Access to Portland

Modern Comfort: Game Room & Access to Portland

Modern Comfort: Game Room & Access to Portland

Modern Comfort: Game Room & Access to Portland

Modern Comfort: Game Room & Access to Portland

3 bedrooms·1 bath

Westbrook • Maine

4(5 reviews)

$1,108.53 USD total for 3 nights

Sep 7 – 10, 2026

Bridgton Bungalow | Brand New, Central & Spacious

5 bedrooms·3 baths

Bridgton • Maine

4.89(27 reviews)

$1,883.63 USD total for 3 nights

Sep 7 – 10, 2026

Bridgton Bungalow | Brand New, Central & Spacious

5 bedrooms·3 baths

Bridgton • Maine

$1,875.38 USD total for 3 nights

Sep 7 – 10, 2026

Long Lake Oasis | Private Lake Access + Views

Long Lake Oasis | Private Lake Access + Views

Long Lake Oasis | Private Lake Access + Views

Long Lake Oasis | Private Lake Access + Views

Long Lake Oasis | Private Lake Access + Views

Long Lake Oasis | Private Lake Access + Views

7 bedrooms·4 baths

Bridgton • Maine

5(17 reviews)

Long Lake Oasis | Private Lake Access + Views

Long Lake Oasis | Private Lake Access + Views

Long Lake Oasis | Private Lake Access + Views

Long Lake Oasis | Private Lake Access + Views

Long Lake Oasis | Private Lake Access + Views

Long Lake Oasis | Private Lake Access + Views

7 bedrooms·4 baths

Bridgton • Maine

$6,236.05 USD total for 3 nights

Sep 7 – 10, 2026

Modern Penthouse in the Old Port

Modern Penthouse in the Old Port

Modern Penthouse in the Old Port

Modern Penthouse in the Old Port

Modern Penthouse in the Old Port

Modern Penthouse in the Old Port

2 bedrooms·1 bath

Portland • Maine

$2,700.00 USD total for 3 nights

Sep 7 – 10, 2026

Luxury Penthouse in Downtown Portland

Luxury Penthouse in Downtown Portland

Luxury Penthouse in Downtown Portland

Luxury Penthouse in Downtown Portland

Luxury Penthouse in Downtown Portland

Luxury Penthouse in Downtown Portland

2 bedrooms·1 bath

Portland • Maine

5(6 reviews)

$605 – $934/ night(excl. fees & taxes)

Luxury Penthouse in Downtown Portland

Luxury Penthouse in Downtown Portland

Luxury Penthouse in Downtown Portland

Luxury Penthouse in Downtown Portland

Luxury Penthouse in Downtown Portland

Luxury Penthouse in Downtown Portland

2 bedrooms·1 bath

Portland • Maine

$12,009.62 USD total for 30 nights

Oct 20 – Nov 19, 2026

Free cancellation

Luxury Penthouse in Downtown Portland

Luxury Penthouse in Downtown Portland

Luxury Penthouse in Downtown Portland

Luxury Penthouse in Downtown Portland

Luxury Penthouse in Downtown Portland

Luxury Penthouse in Downtown Portland

2 bedrooms·1 bath

Portland • Maine

$20,366.65 USD total for 30 nights

Sep 7 – Oct 7, 2026

PWM Airport King Room with Breakfast, Pool & Gym image 1

PWM Airport King Room with Breakfast, Pool & Gym image 2

PWM Airport King Room with Breakfast, Pool & Gym image 3

PWM Airport King Room with Breakfast, Pool & Gym image 4

PWM Airport King Room with Breakfast, Pool & Gym image 5

PWM Airport King Room with Breakfast, Pool & Gym

1 bedroom·1 bath

Portland • Maine

$751.25 USD total for 3 nights

Sep 7 – 10, 2026

PWM Airport 2 Queens Room | Breakfast, Pool & Gym image 1

PWM Airport 2 Queens Room | Breakfast, Pool & Gym image 2

PWM Airport 2 Queens Room | Breakfast, Pool & Gym image 3

PWM Airport 2 Queens Room | Breakfast, Pool & Gym image 4

PWM Airport 2 Queens Room | Breakfast, Pool & Gym image 5

PWM Airport 2 Queens Room | Breakfast, Pool & Gym

1 bedroom·1 bath

Portland • Maine

$804.35 USD total for 3 nights

Sep 7 – 10, 2026

Sweet Home Near Food & Old Port

Sweet Home Near Food & Old Port

Sweet Home Near Food & Old Port

Sweet Home Near Food & Old Port

Sweet Home Near Food & Old Port

Sweet Home Near Food & Old Port

2 bedrooms·1½ baths

Portland • Maine

$1,079.10 USD total for 3 nights

Sep 7 – 10, 2026

Queen bed and extra twin bed

Queen bed with couch setup

TV, and secretary desk

Stairs to second floor room

West End Room Near Top Food & Old Port Attractions

1 bedroom·1 bath

Portland • Maine

5(6 reviews)

$294.30 USD total for 3 nights

Nov 1 – 4, 2026

Free cancellation

Panoramic Sea Views • Oceanic Hot Tub • Epic Food image 1

Back yard features perennials, ornamental shrubs, roses galore and 4 person outdoor hot tub

Panoramic Sea Views • Oceanic Hot Tub • Epic Food image 3

Oversize main bedroom roof deck offers sweeping views of waves crashing on Picnic Point, Whitehead, Cushings Island, moonrise, the Atlantic Ocean, starry skies, boats navigating Whitehead passage, and sometimes even fireworks!

Panoramic Sea Views • Oceanic Hot Tub • Epic Food image 5

Peaks Islnd Seaside Cottage hot tub/decks/walkable

3 bedrooms·2½ baths

Portland • Maine

4.9(48 reviews)

$295 – $1,328/ night(excl. fees & taxes)

Enchanting 3BR Farmhouse Retreat | Nature Getaway

Enchanting 3BR Farmhouse Retreat | Nature Getaway

Enchanting 3BR Farmhouse Retreat | Nature Getaway

Enchanting 3BR Farmhouse Retreat | Nature Getaway

Enchanting 3BR Farmhouse Retreat | Nature Getaway

Enchanting 3BR Farmhouse Retreat | Nature Getaway

3 bedrooms·2 baths

Gorham • Maine

4.56(16 reviews)

$1,250.23 USD total for 3 nights

Sep 7 – 10, 2026

Countryside Oasis: Charming 1BR Farmhouse Getaway

Countryside Oasis: Charming 1BR Farmhouse Getaway

Countryside Oasis: Charming 1BR Farmhouse Getaway

Countryside Oasis: Charming 1BR Farmhouse Getaway

Countryside Oasis: Charming 1BR Farmhouse Getaway

Countryside Oasis: Charming 1BR Farmhouse Getaway

1 bedroom·1 bath

Gorham • Maine

5(17 reviews)

Newly Constructed Two-BR Retreat Near Portland

Newly Constructed Two-BR Retreat Near Portland

Newly Constructed Two-BR Retreat Near Portland

Newly Constructed Two-BR Retreat Near Portland

Newly Constructed Two-BR Retreat Near Portland

Newly Constructed Two-BR Retreat Near Portland

2 bedrooms·1 bath

Gorham • Maine

4.87(15 reviews)

$143 – $424/ night(excl. fees & taxes)

Fowler Farmhouse |Downtown | Beach | Hot tub | Outdoor Oasis!

Fowler Farmhouse |Downtown | Beach | Hot tub | Outdoor Oasis!

Fowler Farmhouse |Downtown | Beach | Hot tub | Outdoor Oasis!

Fowler Farmhouse |Downtown | Beach | Hot tub | Outdoor Oasis!

Fowler Farmhouse |Downtown | Beach | Hot tub | Outdoor Oasis!

Fowler Farmhouse |Downtown | Beach | Hot tub | Outdoor Oasis!

4 bedrooms·2 baths

Bridgton • Maine

5(18 reviews)

Fowler Farmhouse | Downtown | Beach | Hot tub +Bar

Fowler Farmhouse | Downtown | Beach | Hot tub +Bar

Fowler Farmhouse | Downtown | Beach | Hot tub +Bar

Fowler Farmhouse | Downtown | Beach | Hot tub +Bar

Fowler Farmhouse | Downtown | Beach | Hot tub +Bar

Fowler Farmhouse | Downtown | Beach | Hot tub +Bar

4 bedrooms·2 baths

Bridgton • Maine

$1,771.60 USD total for 3 nights

Sep 8 – 11, 2026

Kitchen porch view

Front of the house

Long Lake Escape, fun in all four seasons.

3 bedrooms·1½ baths

Bridgton • Maine

5(8 reviews)

$275 – $315/ night(excl. fees & taxes)

Perley Mills | Private Pond | Hot Tub | Theater

Perley Mills | Private Pond | Hot Tub | Theater

Perley Mills | Private Pond | Hot Tub | Theater

Perley Mills | Private Pond | Hot Tub | Theater

Perley Mills | Private Pond | Hot Tub | Theater

Perley Mills | Private Pond | Hot Tub | Theater

4 bedrooms·3 baths

Denmark • Maine

Victorian Farmhouse | Walk to Saco River

Victorian Farmhouse | Walk to Saco River

Victorian Farmhouse | Walk to Saco River

Victorian Farmhouse | Walk to Saco River

Victorian Farmhouse | Walk to Saco River

Victorian Farmhouse | Walk to Saco River

3 bedrooms·2 baths

Buxton • Maine

$1,248.05 USD total for 3 nights

Sep 24 – 27, 2026